Founding Partners

On a balmy June evening in 1790, the enslaved chef James Hemings was putting the final touches on a meal that, according to his master Thomas Jefferson, would “save the Union.” Jefferson had recently returned from five tranquil years in France. He’d dreamed of retreating to his Monticello plantation in Virginia, where he would farm, renovate the house, read books, and entertain friends. Instead, soon after his arrival, he had reluctantly agreed to serve as George Washington’s secretary of state, a daunting task that left him with migraines for the better part of the previous month. Even worse, his position required relocating to the capital in New York and renting a small house at 57 Maiden Lane, a far cry from the spacious home he was used to at Monticello. The cramped quarters left him longing for his former life, but on this night he had no time for distraction: This dinner, from the food to the conversation, had to be executed to perfection.

He asked Hemings to prepare each course in advance, laying everything out neatly on dumbwaiters. That way, no servants would enter the dining room and potentially leak what they heard to outsiders. For his plan to work, secrecy was essential. Hemings carefully reviewed each menu item: no less than five rare wines; green salad and jelly; two main courses of Virginia ham and beef stew; an array of sweets including meringues, macaroons, and vanilla ice cream.

The lavish spread seemed fit for a crowd, but only two guests arrived that night: Alexander Hamilton and James Madison. To Jefferson’s relief, the fancy food and fine wine put both men at ease, especially Hamilton. The previous day, Jefferson had encountered Hamilton in front of Washington’s office, looking “somber, haggard, and dejected beyond comparison.” Even his clothes, in Jefferson’s recollection, appeared “uncouth and neglected.” The purpose of this “little dinner” was to broach the topic causing Hamilton’s distress.

Hamilton, as secretary of the treasury, had warned Jefferson that the fragile, three-year-old experiment in republican government would soon “burst and vanish.” He placed the blame on none other than Jefferson’s closest friend, Madison. It was Madison who was leading Southern congressmen to block Hamilton’s prized fiscal proposal: to create a national bank that would pay off states’ debts from the Revolutionary War. Madison strongly opposed this “assumption” of debts, believing it would give too much power to the central government at the expense of Southern states.

But in the comforts of Jefferson’s home, sipping on French brandy after the main meal, Madison and Hamilton finally reached an agreement that had eluded the legislature for months. The South would support the federal assumption of states’ debts in exchange for the relocation of the capital from New York City to the banks of the Potomac River, right outside Virginia.

In the words of historian Joseph Ellis, this Dinner Table Bargain should “rank alongside the Missouri Compromise and the Compromise of 1850 as one of the landmark accommodations in American politics.” Months of backroom maneuvering had yielded no progress; it was only after Jefferson’s dinner that the deadlocked legislature finally passed the Residence and Funding Acts. The first great political crisis of the nascent republic had been averted, a deadlock many statesmen had feared would destroy the country.

On a more intimate level, the dinner marked the height of a potent political partnership, the so-called “great collaboration” between Jefferson and Madison. While Jefferson portrayed himself as a neutral mediator that June night, he had already sided firmly with Madison on the need to rein in the “monarchist” Hamilton. This alliance between Jefferson and Madison was by no means assured. Only a few years earlier, any “great collaboration” would have better described the partnership between Madison and Hamilton, now sworn enemies. At the outset of the Revolutionary era, it was Madison and Jefferson who differed vastly both in how they related personally and how they thought politically. Now, in 1790, fifteen years into their complex and layered friendship, the two patriarchs had managed to find common ground. The story of that convergence reflects the story of America’s own shifting political tides. As their friendship evolved and deepened, Jefferson and Madison jointly developed our nation’s highest ideals and, with them, the hybrid foundation for our democracy.

In popular American history, Jefferson is typically portrayed as the dominant player in his partnership with Madison, more charismatic, vigorous, and ultimately successful. In a literal sense, the depiction is accurate: The six-foot-three-inch Jefferson did tower over the five-foot-four-inch Madison. While Jefferson appeared more intense and manly, Madison looked colorless and fragile, never weighing more than one hundred pounds. The physical differences translated to temperamental ones as well. The fundamentally optimistic Jefferson exuded charisma, while Madison was a chronic worrier often paralyzed by shyness. Madison’s delicate health stemmed from hypochondria, defined then as a disease afflicting those who studied too much. Plagued by a slew of physical ailments and depression, Madison once confessed to a friend that he anticipated dying young. With his dark clothes and feeble voice, “little Jemmy” (as his colleagues nicknamed him) in no way came across as the commanding, self-confident figure that Jefferson was.

These superficial differences have only enhanced the impression of Jefferson’s singular status. The popular image is of Jefferson perched heroically atop his Windsor chair, quill pen poised to write that epic phrase “all men are created equal.” Madison, though recognized as the “Father of the Constitution,” still tends to be consigned to the role of Jefferson’s trusty lieutenant, a junior member forced to rely on a senior leader for his own later prominence. In some ways, this characterization rings true. Madison did serve largely as Jefferson’s political wingman, especially amid the divisions of the 1790s, then as his secretary of state and ultimately his presidential successor. Later in life, a pattern seemed to emerge: Jefferson would communicate the overarching vision, while Madison would manage the messy details, offering advice and quietly editing Jefferson’s speeches and writings.

But appearances can also be illusory; in this case, they surely don’t tell the true story of a friendship that was in fact much more equal than popular lore has long held. Madison’s readiness to linger in Jefferson’s shadow masked and even distorted the extent to which he actually possessed independent power in the relationship—one that lasted for half a century and encompassed nearly 1,250 letters. Those letters ranged from casual notes to more extended essays, such as Madison’s seventeen-page description to Jefferson of the Constitutional Convention. Their closeness was apparent in how easily they switched between sharing the meaningful and the mundane. Plots against Hamilton might be interspersed with jokes about “the mystery of the missing pecans” that Madison had tried sending unsuccessfully to Jefferson in France. Occasionally, the two men would even write in code to conceal gossipy tidbits about their famous contemporaries. They also shared more blunt assessments of their enemies, such as one December 1784 letter, in which Jefferson expressed their mutual wish for Patrick Henry’s downfall: “What we have to do I think is devoutly pray for his death.” Such candidness and cattiness showed how much they considered themselves equals, with mutual respect and devotion for one another. Their seamless collaboration, wrote John Quincy Adams, resembled “a phenomenon, like the invisible and mysterious movements of the magnet in the physical world.”

As Adams recognized, Jefferson and Madison’s magnetic attraction partly stemmed from their opposite charges. Their contemporaries repeatedly pointed out that the two giants were not simply dissimilar in looks but in abilities. Jefferson was more imaginative and creative; Madison was more prudent and systematic. Jefferson wrote with greater eloquence and facility, Madison with heightened persuasion and analysis. Jefferson was lofty in his thinking; Madison was anchored in reality. In short, their partnership embodied the human equivalent of checks and balances. For Jefferson to be Jefferson—big thinking and idealistic to the max—he needed as his stabilizer and actualizer the more practical, cautious Madison.

For all their contrasts, Jefferson and Madison were bound by one vital feature: They were proud sons of Virginia. Indeed, their determination to broker the Dinner Table Bargain stemmed first from an unflinching loyalty to their native state. They viewed the location of the District of Columbia on the Potomac as proof of Virginia’s centrality to national governance. As Joseph Ellis points out, though their stance reflected a certain provincialism, Virginia in the late 1700s did possess one-fifth of the country’s population and contributed one-third of its trade. When John Adams quipped that “in Virginia all geese are swans,” he meant to capture the conviction among the Virginia gentry that their state had stood at the forefront of the Revolutionary War. Both Madison and Jefferson held deeply to this belief, and it persisted even through all their disagreements.

Of course, their faith in Virginia’s superiority rested on an uncomfortable fact: Both were wealthy Southern farmers who possessed large plantations that relied heavily on slave labor. Though they claimed to detest slavery, they never ceased to own slaves or to temper their paternalistic and racist judgments. Though Madison entertained ideas about gradual emancipation and exporting freed slaves to Africa, he never fully reconciled his economic interests with his theoretical musings. His four-thousand-acre Montpelier estate, less than thirty miles from Jefferson’s Monticello, was tended by more than one hundred slaves, none of whom he ever freed. Most notoriously, it was Madison who proposed during the Constitutional Convention that slaves, as property, should be counted as only three-fifths of a person.

And Jefferson—the same man who famously proclaimed that “all men are created equal”—could just as easily insist on the inferiority of Black people, describing them as being “incapable as children.” One of the largest slaveowners in Albemarle County, Jefferson held 607 slaves over his lifetime. It was the kind of contradiction that seeped into Jefferson’s own family as well. James Hemings, the slave who cooked Jefferson’s legendary 1790 dinner, was the older brother of Sally Hemings—another of Jefferson’s slaves, the mixed-race half sister of his wife and likely the mother of six of his twelve children. One of those six children, James Madison Hemings, was named after Jefferson’s best friend.

This mixture of intimacy and inhumanity defined the personal and political lives of both Jefferson and Madison. It hovered in the background of their existences and formed the subtext of nearly every discussion the two men shared about the emergent nation’s future.

So much of how we can understand Jefferson and Madison’s friendship today must be learned through subtext—the deeper meaning hidden beneath the surface of their words. Unlike other First Friends, they were often separated by long physical distances. Consequently, their bond had to develop mostly through the written word—letters—not by casual get-togethers in favorite haunts. Both were prolific writers at a time when print culture dominated; political arguments were made and disseminated through letters as much as by newspapers, broadsides, and pamphlets. Yet none of this dissemination—no matter how urgent—was ever instant. Months might pass before even the most important news could be received. Political gossip had to traverse undeveloped terrain or linger aboard slow-moving ships. In short, most communication required patience, investing each letter with considerable weight and gravity.

When Jefferson and Madison wrote one another, their words were not particularly effusive or evocative. For both men, words needed to be carefully chosen and considered, often alluding to an emotion but rarely stating it directly. This restraint was also partly a function of who Jefferson and Madison were: two serious, highly intellectual philosopher-statesmen, the only First Friends who would both go on to serve as president. Born and bred into leadership, their primary way of signifying trust and closeness was through abstract meditations on democracy, government, and human nature. Though occasionally there were glimmers of shared jokes and stinging opinions, most of their correspondence initially appears rather dull and formal by today’s standards.

To appreciate this particular friendship, we must accept it then as a product of its own time with its own peculiarities. Through it, we can also better perceive the intricate nature of our national experiment. For two such powerful men during the Revolutionary era, personal identity was inseparable from national identity. As Jefferson and Madison first clashed then grew into intimate friends, they were also working out the contours and character of America itself.

Born in 1751, James Madison was the oldest of eleven children, surrounded by brothers and sisters to play with on the rich, red soil of their family’s Piedmont plantation. From the beginning, Madison’s life benefited from the privileges of inheritance. His father, James Madison Sr., was the wealthiest man in Orange County, himself the beneficiary of a long line of English ancestors who had accumulated fortunes in Virginia more than a century before. As his family grew, the senior Madison had a mansion built on his vast lands and proudly named it Montpelier, meaning “Mount of the Pilgrim.” With ample space and supportive parents, the young Madison enjoyed a largely happy childhood. But what marred those early years—what gave him a sobering view of reality—was his frail health, including a digestive disease that forced him to stick to a bland diet of gruel. From an early age, Madison knew intimately the fragility of his own body and of life itself.

The one benefit of Madison’s bad health was that it encouraged his studiousness (though his studiousness would also worsen his health). Before reaching his teens, he was already reading the works of Greek and Roman philosophers—Virgil, Homer, Ovid, Plato, Plutarch—as well as the great Enlightenment thinkers like Locke and Montesquieu. He was so precocious that at age eleven his father sent him away from home to attend an advanced boarding school in neighboring King and Queen County. After five years of intense study, he returned home for two more years of private lessons with a local minister. By 1769, the eighteen-year-old Madison was ready for college, but his father wanted to get him away from Virginia’s unhealthy tidewaters. So rather than the College of William and Mary, which most Virginians—including Jefferson—attended, Madison left for the College of New Jersey (now Princeton).

Arriving in Princeton in 1769, Madison soon showed how much his classical education had overprepared him for college. He easily aced all the exams needed to skip his entire freshman year. He then started a rigorous study regimen, one that the college’s new president, the Reverend John Witherspoon, believed would demonstrate the school’s superiority over its rivals to the north at Harvard and Yale. Madison more than lived up to Witherspoon’s high standards, cramming three years of college into two (in part by going weeks at a time sleeping only five hours a night).

But cruising through college proved to be a near-fatal mistake. Soon after completing his studies, the young man collapsed, too ill to make the three-hundred-mile journey back home. Instead of relaxing after this scare, Madison plowed ahead, lingering at Princeton for another year to take more classes. In the fall of 1772, he finally returned home—twenty-one years old, worn out by his declining health, and loath to become a farmer in the remote hill country. He began suffering from seizures, which kept him home for three more years. While recuperating, he read books, wrote to college friends, and contemplated his uncertain future. He began studying law, but he lacked passion for the subject and never intended to practice. The next common choice for any Princeton graduate—the ministry—seemed equally dreary.

In 1774, with better health but still directionless, Madison decided to embark on a trip to Pennsylvania to visit his friend William Bradford, who came from a prominent Philadelphia printing family. There, Madison witnessed something he’d never seen before: riotous street demonstrations in support of the Boston Tea Party, when a group of colonists had protested British taxes by dumping chests of tea into Boston Harbor. For the first time in his life, Madison felt truly inspired, marking the beginning of his fascination with Revolutionary politics. Once back in Virginia, he asked Bradford to send him regular updates on the political scene. Aimless until then, Madison had finally found his life’s mission in the ferment that would become the American Revolution.

When war broke out at Lexington and Concord in 1775, Madison joined the Orange County militia as a colonel, elected because of his father’s local importance. Before he could even take the battlefield, it became clear that the sickly Madison was far better suited to safer confines, like a legislative body. In less than six months, he resigned from the militia to accept a more fitting, elected position in the House of Delegates during Virginia’s Convention of 1776, a moment that forever altered the course of his life.

In April 1776, the twenty-five-year-old Madison ventured into Williamsburg and took his seat among this illustrious body of politicians. It was here that he would soon meet Jefferson, an impressive, reddish-haired man eight years his senior. Jefferson had already made a name for himself after writing the “Summary View of the Rights of British America” two years earlier, in 1774. That pamphlet propelled him to prominence in the Revolutionary cause, highlighting his exceptional ability to articulate the colonial yearning for independence. While Jefferson stood on the brink of penning an even more revered document, the Declaration of Independence, Madison could boast of little else than untapped potential. Fifty years later, Jefferson recalled his rather humdrum first impression: “Mr. Madison came into the House in 1776, a new member and young: which circumstances, concurring with his extreme modesty, prevented his venturing himself in debate.”

Jefferson wasn’t exaggerating in describing Madison’s first venture into public life. Throughout the proceedings, as Virginia adopted a new constitution, Madison kept his mouth shut, more than happy to let established politicians like Jefferson dominate the spotlight. It certainly didn’t help that his many ailments left him with a weak and reedy voice; it was so incapable of projecting that he wouldn’t even attempt to speak in public until he turned thirty years old. But Madison’s silence foreshadowed the style for which he would soon become celebrated: He watched closely, quietly took everything in, studied intently, until one day when his genius would catch everyone off guard.

Later that fall, when the Virginia legislature began a debate over religious freedom, Madison was awed by Jefferson’s eloquence in arguing his case for the separation of church and state. From Madison’s standpoint, Jefferson was as (if not more) articulate than one of his heroes, the dynamic Patrick Henry, known for his uncompromising motto, “Give me Liberty or Give me Death!” Madison entered politics as a rapt observer of firebrands like Henry and Jefferson, stirred by their charisma but sensitive to their untouchable status—and his own inadequacies. As Madison would recall decades later, Jefferson paid scant attention to him at the time because of “the disparities between us.” Jefferson seemed to be everything Madison was not: tall, dashing, and outgoing, with a rare gift for coining pithy phrases and witticisms. Little did Madison know then, but even at that very moment, the student was evolving into the master.

Before “little Jemmy” met that hallowed author of the Declaration, Jefferson was just a scrawny daydreamer growing up in Virginia’s Blue Ridge Mountains. He idolized his father, Peter, a strapping frontiersman who had served in the House of Burgesses. Peter Jefferson’s main focus seems to have been trying to transform the lanky boy into a robust Virginian man like himself. At one point, Peter sent young Thomas into the woods with a gun to fetch a wild turkey. Jefferson fired his shots but each one missed—until he stumbled across a turkey trapped in a pen. He tied the unlucky bird to a tree and shot it point-blank. Despite this failed attempt, Peter continued his project to toughen up his son. But Thomas remained a bookworm, reading everything he could find in the family’s small library.

When Peter Jefferson died, fourteen-year-old Thomas was left reeling, unable to rely on books for concrete solutions. There were, though, the familiar benefits of inheritance to soften the blow. As the older son, Jefferson received his father’s Shadwell plantation, totaling more than five thousand acres of land—a blessing that eased his worries over money and allowed his imagination to blossom.

In 1760, at the age of seventeen, Jefferson enrolled in the College of William and Mary. As a country boy, he began his college years feeling self-conscious around the scions of Virginia’s leading families. To compensate, he cloaked his insecurity with diligence. As one friend recalled: “He used to be seen with his Greek grammar in his hand while his comrades were enjoying relaxation.” According to family legend, he would sometimes study fifteen hours a day, building the same strong foundation in classical and Enlightenment thought that Madison would. In 1762, he was introduced to George Wythe, one of colonial America’s most renowned lawyers, who took Jefferson under his wing and honed his legal mind and writing talents.

For five years, Jefferson studied law under Wythe just as the legal profession was gaining greater standing. Wythe taught Jefferson invaluable lessons about how to fill his time: reading law in the morning; exploring political philosophy and political economy in the afternoon. According to fellow attorney William Wirt, Jefferson absorbed from Wythe an “unrivaled neatness, system, and method in business.” He also learned to write. His goal was to be able to recap legal cases as succinctly as possible, “never using two words where one will do.” After countless hours studying and writing, Jefferson grew more and more convinced that law could be used to structure and shape society.

After he had completed his studies with Wythe, Jefferson joined Virginia’s House of Burgesses, establishing his reputation as a highly respected lawyer and a strong advocate for Virginia’s legal reform. His social life skyrocketed in turn; he began mingling with members of Williamsburg’s most elite circles. Friends orbited around him, drawn to Jefferson’s warmth and good humor. One of those friends happened to be Madison’s cousin, who (confusingly) was also named James Madison. Then, in 1770, Jefferson began courting a twenty-two-year-old widow named Martha Wayles Skelton, one year his junior and the daughter of John Wayles, also a successful lawyer who made handsome profits as a slave trader. The father disapproved of his daughter’s new beau, but the increasingly serious couple ignored his opposition.

Giddy with passion and full of resources, Jefferson finally began to tackle a project he’d been fantasizing about for years: the construction of a mansion on an 857-foot summit a mile outside Charlottesville. Jefferson inherited the peak from his father and, as a teen, had wandered on the slopes dreaming of one day building a house there. He spent months sketching and planning, then recruited a year’s worth of slave labor to transform his one-room cottage into something much more regal: a neoclassical villa with a shining dome and snow-white columns. Jefferson christened the estate “Monticello,” meaning “little mountain” or “hillock.”

In creating Monticello, Jefferson was not just preparing for his future with Martha but straining to secure the approval of Martha’s father. His hard efforts paid off. On November 11, 1771, John Wayles finally gave his permission and only two months later, on New Year’s Day of 1772, the young couple wed. When John Wayles died a year later, Jefferson and his new bride found themselves with even greater riches: 11,000 additional acres and 142 slaves. With this massive inheritance, Jefferson now was set for life, free to be a gentleman farmer and needing only his family, his fields, and his books.

At the very moment the world opened itself up to his brilliance and ambition, Jefferson retreated. At heart a homebody, Jefferson became deeply ambivalent about being a lawyer, preferring instead to remain a farmer. The irony is that while the reserved Madison steadily ascended the ranks of Revolutionary leaders, the more sociable Jefferson often preferred a simpler, quieter existence. In 1774, for the first of many times, he took steps toward abandoning his profession so that he could lead an idyllic life on his hilltop. He gave up his busy law practice, hoping to prove his steadfast loyalty to Martha as she struggled through multiple pregnancies. Day after day, month after month, Jefferson devoted himself to her, only occasionally fulfilling his legislative duties. He saw himself willingly and happily living the rest of his life on Monticello—reading his favorite books with Martha, doting on their babies, far from the tumult of Virginia politics.

Until, that is, events on the horizon forced Jefferson to descend from his sheltered hilltop world.

The Revolution that ignited in Boston in April 1775 spread across the rest of the colonies, turning local clashes into full-scale war. For Madison, this moment finally gave him the opportunity to prove himself—to show Virginia’s political elders what a remarkable mind and keen judgment he truly had. Jefferson, meanwhile, did not share Madison’s excitement, confessing to his cousin John Randolph that he longed for the day when “this unnatural contest” with Britain would end. Only then, Jefferson wrote, could he “withdraw [himself] totally from the public stage and pass the rest of [his] days in domestic ease and tranquility.”

Unfortunately for Jefferson, the word “tranquility” turned out to be overly optimistic. The strains of childbirth had so weakened Martha that Jefferson needed to curtail his public responsibilities, even refusing an appointment as commissioner to France. For the ensuing months, he split his time between the Continental Congress and Monticello, torn between his loyalty to the Revolutionary cause and his romantic wish to simply stay home.

In the end, a quiet domestic life was never a realistic option. Especially after the acclaim he received for authoring the Declaration of Independence, Jefferson could do little to avoid the drama engulfing the land. By 1779, he was elected governor of Virginia, a triumph that coincided with a hiccup in Madison’s own ascent. In the first real political contest of his life, Madison had lost his race for re-election to the 1777 session of the Virginia House of Delegates. He had refused to accede to the local tradition of plying voters with whiskey and beer as they gathered first to drink and then vote. His opponent, a tavern owner, showed no such reluctance. A decision Madison thought noble was instead interpreted as cheap, teaching Madison an expensive lesson. But all was not lost. In less than six months, his former colleagues in the House appointed him to the Council of State, a newly formed body to ratify decisions made by the governor. Working together daily, Jefferson soon noticed that Madison’s unassuming presence belied his shrewd political skill, and he began turning to him as his primary confidant and friend. As Madison remembered years later, it was during this time, three years after their initial meeting, that “a friendship was formed, which was for life.”

Their increasing closeness could not have come at a better time for both men and for the cause to which they were committed. As Madison achieved greater renown in state politics, fighting for such causes as religious freedom, Jefferson entered the lowest point of his life, both publicly and privately. Foreshadowing criticism of dilettantism that would dog him years later, many leaders disapproved of how Jefferson split his time between Monticello and politics. But Madison remained sympathetic and loyal, providing Jefferson with a constant stream of news from Philadelphia, where he began serving in 1780 as Virginia’s youngest delegate to the Continental Congress. For the next few years, as Jefferson grappled with problems at home and as Virginia governor, Madison emerged as an unwavering source of emotional support. It is no coincidence that during this period, Madison began signing his letters “your sincere friend” rather than his usual “your obedient servant.”

The first great challenge that Jefferson faced as governor unfolded just after New Year’s Day in 1781. British troops, led by the traitor Benedict Arnold, stormed into Virginia and destroyed the capital in Richmond. Braving harsh winter weather, Martha hastily packed some things and fled with her infant girl. Meanwhile, Jefferson frantically tried to rally the state’s militia, but only two hundred men showed up. Vastly outnumbered, he could do nothing but sit powerlessly on his horse near the James River, watching as Arnold ravaged buildings, looted homes, and burned property. Only a few months later, in April, Jefferson and Martha’s newborn daughter died, devastating both parents. They had no time to grieve; in May, the British again invaded Virginia with seven thousand men.

In the midst of these dual crises, Jefferson did the unthinkable: He informed his council and state legislature that he would not accept a third term as governor. He had done his duty for two years; now, more than ever, he needed some time to himself. Many outsiders, including Jefferson’s former friend and Virginia’s ex-governor Patrick Henry, condemned Jefferson for shirking his duties at the worst possible time. Madison himself urged Jefferson to reconsider, confessing that he was “lamenting that the state… in the present crisis” could not afford “to lose the benefit of your administration.” Jefferson ignored even Madison’s pleas, and whisked Martha and the children away to Monticello.

But the mountain hideaway was not as impervious as Jefferson believed. On June 4, Jefferson received news that Lord Cornwallis had ordered a British strike force to invade Charlottesville with the specific goal of capturing him—the ultimate prize as the state’s governor and the Declaration’s author. This attack presented a final, unforgiving reflection of Jefferson’s failed governorship, as Virginia again could do nothing to block Cornwallis’s dragoons from entering the state. Despite this reality, Jefferson had already resolved that he would no longer try to manage the war. His sole priority was simply to escape with his family to the last remaining refuge, Poplar Forest, where he owned a small plantation. They hid there, in the woods, for the next few months.

Finally, in October 1781, with pressure from both the French and an American army led by George Washington, the British under Cornwallis were forced to retreat, ultimately surrendering at Yorktown. America had won the Revolutionary War. Madison joined the jubilant celebrations in Philadelphia, but Jefferson enjoyed no such reprieve. While out for a morning ride in Poplar Forest, he had been thrown from his saddle and broken his wrist. During his six-week recuperation, he received a letter from a friend revealing that an investigation was being launched, led by Patrick Henry, that would assess his conduct as governor. The implication was that Jefferson had failed to properly defend Richmond from invasion by Arnold and Cornwallis and, even worse, that he was a coward. Jefferson, unused to being ridiculed, believed that his reputation had been damaged forever.

When the Virginia Assembly met in late fall, Jefferson stood ready to defend himself against all accusations. Henry gleefully read a list of charges, but they went nowhere. Without any debate, the assembly passed a resolution affirming its faith in Jefferson’s “ability, rectitude, and integrity as chief magistrate of this commonwealth.” Madison, meanwhile, showed how deeply he understood Jefferson’s sensitive nature and especially his fear of rejection. Rather than penning a gushy letter to express his sorrow over Jefferson’s embarrassing situation, he simply sidestepped the topic altogether. In the midst of the investigation, Madison blithely wrote to Jefferson about western expansion, then signed off: “With great respect and sincere regard.” Once again, subtext was key: By focusing on what was “important”—thus ignoring the elephant in the room—Madison was implicitly showing his confidence in Jefferson’s innocence and his faith that his friend would be redeemed. The Assembly ultimately agreed in returning a not-guilty verdict.

But if Madison thought that the vindication would heal Jefferson’s wounded pride, he was wrong. Rather than resuming his duties, Jefferson claimed that this whole ordeal had ruined his appetite for future public service and that “these injuries… will only be cured by the all-healing grave.” He then retreated to Monticello once again, announcing in a note to his distant cousin Edmund Randolph, “I have retired to my farm, my family and books, from which I think nothing will ever more separate me.”

Freed of responsibilities, it seemed at first as if happiness had finally returned to Jefferson’s life. On May 8, 1782, Martha gave birth to another baby girl. But the labor was an arduous one, especially since she had never fully recovered from having to flee Richmond and Monticello. Martha died four months later on September 6, 1782. Already ashamed over being investigated by his peers, Jefferson was shattered by his wife’s death. For three weeks, he went into isolation at Monticello, consumed by grief and guilt. He shut himself in his room, pacing back and forth in despair, then burned every single letter to and from Martha.

A concerned Madison went into action, determined to get Jefferson away from Monticello, now a haunted place. He began lobbying the Confederation Congress to send Jefferson to Paris, where Benjamin Franklin, John Adams, and John Jay were negotiating a peace treaty with the British after the surrender at Yorktown. Madison knew that such a trip would not simply benefit the nation; it would place Jefferson in a new setting that would soothe his grief and perhaps moderate his attachment to home. After Madison’s repeated encouragement, Jefferson grimly accepted the appointment. In January 1783, he arrived in Philadelphia to lodge with Madison while awaiting his departure to Paris.

While living with Madison at Mary House’s upscale boardinghouse, Jefferson noticed something surprising: Madison had begun courting a fifteen-year-old woman named Catherine “Kitty” Floyd. Kitty was the daughter of a Continental Congress delegate from New York, William Floyd, who roomed at the same boardinghouse and was an acquaintance and political supporter of Jefferson. While most men during that era married by their midtwenties, the thirty-two-year-old Madison was still a frustrated bachelor. He had never been an appealing catch, given his introverted nature and a bald spot he tried to conceal by brushing downward his last few strands of hair. The wife of a fellow Virginia delegate compared him to the stylish European emissaries visiting Philadelphia and found him wanting: “Mr Madison, a gloomy, stiff creature, they say is clever in Congress, but out of it there is nothing engaging or even bearable in his manners—the most unsociable creature in existence.”

Luckily, Madison could rely on Jefferson to tone down at least some of this awkwardness. With frosty winter weather delaying his departure to Paris, Jefferson continued to linger in Philadelphia, encouraging his friend’s blossoming romance. He effectively served as a middleman, passing on Madison’s “compliments” to Kitty and then relaying how Kitty had responded. In April 1783, Jefferson returned briefly to Monticello after Congress withdrew his appointment as a peace commissioner; the Treaty of Paris had been negotiated before he could leave. His disappointment was short-lived, however, since the Virginia legislature elected him a delegate to the Confederation Congress only a month later. While easing back into affairs of state, he continued pushing Madison to propose marriage, even admitting his hand in convincing her to marry him: “I often made it the subject of conversation, more, exhortation with her,” Jefferson wrote. Consequently, “I… was able to convince myself that [Kitty] possessed every sentiment in your favor which you could wish.”

But only a few months later, on August 11, 1783, Madison wrote a coded letter to Jefferson disclosing devastating news: Kitty had fallen in love with a more age-appropriate, nineteen-year-old medical student named William Clarkson. Jefferson tried his best to console the crushed Madison, admitting that “no event has been more contrary to my expectations,” yet reassuring him that “the world still presents the same and many other resources of happiness, and you possess many within yourself.” But it was now Madison’s turn to grieve. For weeks afterward, he did his best to avoid social situations and wrote letters only to his family and closest friends.

For the rest of his life, Madison never got over Kitty’s brutal rejection, even after he married Dolley Payne Todd more than a decade later. When he was nearly eighty years old, he stumbled across two letters he had written to Jefferson about Kitty. Rereading those letters so upset him that he passionately scribbled out all the references to his long-lost love and pushed the papers to the bottom of his files.

Their shared emotional torment bonded the two friends tightly, but the world was moving forward fast, with little time to indulge their grief. Though heartbroken, Madison was not one for self-pity. He remained an attentive friend, aware that Jefferson’s anguish over losing Martha persisted despite his resumption of various public duties. After masterfully orchestrating the Congress’ ratification of the Treaty of Paris shortly after New Year’s Day 1784, Jefferson felt readier than ever for, in his words, “a change of scene.” The Confederation Congress now agreed to add Jefferson to its mission in Europe, joining Franklin and Adams in helping to fortify the nation’s new alliances. The day after his ambassadorship was made official, Jefferson told Madison that he intended to stick to the same principles that informed his public life thus far: “I shall pursue there the line I have pursued here; convinced that it can never be the interest of any party to do what is unjust, or to ask what is unequal.”

In July 1784, at a turning point in both of their lives, Jefferson finally moved to France, where he would stay for the next five years. Before his departure, Jefferson asked two things of Madison: first, to care for his favorite nephew, Peter Carr, whose father had died a few years before; and second, “to continue to favor me with your correspondence” as the new nation embarked on creating a government.

Madison’s moment to emerge from Jefferson’s shadow finally came in May 1787, when he began serving as a delegate to the Constitutional Convention in Philadelphia. Always the overachiever, he arrived in Philadelphia a full eleven days before the Convention’s start date. None of the other members of the Virginia delegation had come yet, slowed by heavy rainstorms that turned the dirt roads into muddy bogs. As Madison waited, he experienced a bittersweet sense of déjà vu. Once again, he was staying at Mary House’s boardinghouse, where he and Jefferson had lived together when his ill-fated romance with Kitty began.

Now both Kitty and Jefferson were gone, but Madison comforted himself knowing that he could still communicate with one of them. The two friends began exchanging gifts that marked their current obsessions and endeavors. Jefferson mostly sent books about political philosophy, European governments, and failed democracies, as well as contraptions like a telescope that retracted into a cane, phosphoretic matches, a pedometer, and a box of chemicals to further indulge Madison’s growing interest in chemistry. Madison dispatched various wildlife unique to America, including sugar maples, Pippin apples, and pecans. One thing he failed to procure was Jefferson’s request for a live opossum.

Interspersed between the plants and animals, gizmos and gadgets, they also shared the latest political news. Jefferson described his fascination with France, which was undergoing its own revolution that had not yet turned violent. Madison provided the insider details of the upcoming Convention, barely concealing his anticipation. “Nothing can exceed the universal anxiety for the event of meeting here,” he confessed to Jefferson. He tackled this anxiety as he always had: by immersing himself in the books that Jefferson sent his way, books that enabled him to conceptualize the idealized contours of a new centralized government. At the same time, Jefferson continued to envision a life beyond politics, proposing that upon his return, they become neighbors in Virginia’s mountains. He had identified a large property adjoining Monticello, reassuring Madison that it was “all within two miles, all of good land.” Though moved by Jefferson’s “affectionate invitation,” Madison deferred, reflecting, as Noah Feldman writes, “Madison’s quiet sense of independence, even from Jefferson… He intended to become master of his own house.” Though their correspondence remained as open and candid as ever, the two men would soon find themselves separated by more than just an ocean.

Hints of tension in their friendship began to emerge even before Madison’s work on the Constitution formally began. In August 1786, an armed uprising erupted in Massachusetts among farmers who had fought in the Revolutionary War. Led by Daniel Shays, a former captain in the Revolutionary Army, these veterans were protesting the poverty and debt crisis caused by the state’s heavy taxes. By the beginning of 1787, the protest had flared into uncontrolled violence, as the Shaysites attempted to overthrow the Massachusetts government. The federal government found itself unable to muster the troops needed to stifle the revolt, leaving Massachusetts to fend for itself.

For many observers, including Madison, Shays’ Rebellion seemed to prove the necessity of replacing the weak Articles of Confederation and creating a newly empowered federal government. Madison viewed the Shaysites as dangerous rebels whose populist rage threatened to topple the republican experiment. But Jefferson—watching from afar—expressed blithe approval, writing to Madison, “I hold it that a little rebellion now and then is a good thing, and as necessary in the political world as storms in the physical.” From Jefferson’s perspective, the “tree of Liberty” occasionally required “the blood of patriots & tyrants” as fertilizer. The divergence could not have been more dramatic, serving as a stark foreshadowing of what was to come.

Neither Madison nor Jefferson allowed their contrary opinions of Shays’ Rebellion to interrupt the flow of their correspondence, which remained constant and increasingly frank, until the business of drafting a new federal constitution could begin during the summer of 1787. Madison would have happily continued to provide Jefferson with regular updates, but the conferees agreed that no details of their deliberations should be discussed with anyone outside the room until the convention ended. That rule deprived Jefferson of news for nearly half a year, but it enabled Madison to evolve into the ideal narrator. Madison not only had come more prepared with more concrete ideas than any other delegate, but he also placed himself (literally) at the center of the convention itself. He sat in the exact middle of the front row, and from that desk he kept the most complete set of notes of each day’s proceedings. Once the convention concluded in September 1787 with the signing of the Constitution, the friends freely resumed their correspondence. And it was this set of pivotal correspondence that highlighted for the first time their divergent views about the American character, republican government, and democracy itself.

For Jefferson, nearly four thousand miles and an ocean away from his home country, sweeping constitutional reform lacked urgency. As a supreme idealist—someone who fantasized about spending his days on a secluded farm—Jefferson held an almost instinctive hostility to any form of authority outside of the individual. In modern parlance, it’s possible Jefferson would have identified as a kind of libertarian—and many libertarians today view him as their chief intellectual ancestor. He saw centralized political power as dangerous and wanted as many decisions as possible to be made by “the people” at the state level. But for Madison, positioned in the thick of the drama, nothing could have been more urgent for the republic’s survival than total reform. The solution, Madison believed, lay in creating a strong national government with adequate checks and balances: a unitary executive with limited powers, appointed by electors chosen by the people; a large legislative body elected by the people, with significant and enumerated powers; a smaller but more senior body chosen by the elites; and a judiciary appointed by the executive subject to agreement of the Senate. Ultimately, nearly all of Madison’s original conceptions were incorporated into the ratified Constitution. On October 24, 1787, Madison sent Jefferson a detailed analysis of what had transpired in Philadelphia. Before enumerating the specifics of what was won and lost in the final agreement, he extolled the sheer improbability of what had been achieved: The “task,” he wrote, was “more difficult than can be well conceived by those who were not concerned in the execution of it.” Given how complicated the subject matter and opinionated the conferees, “it is impossible to consider the degree of concord which ultimately prevailed as less than a miracle.” Over the next sixteen pages, Madison laid out the shape of the new government to the one person whose opinion he most valued.

Jefferson’s response, written two months later, shows how far the two friends occupied opposite ends of a great political divide. The issue separating them was the very role of the government Madison was laboring to create. Jefferson expressed his central worries about the Constitution as it stood: “I own I am not a friend to a very energetic government.… After all, it is my principle that the will of the Majority should always prevail.” But Madison’s whole point was that majority rule posed the biggest threat to democracy, and that the Constitution’s main job was to curb such factions. In short, Jefferson feared that the Constitution overreached in curtailing liberty, while Madison felt that the document did not go far enough in containing popular passions.

In the same letter, Jefferson told Madison that he agreed with the idea of dividing power into three branches, governed by the idea of “checks and balances.” But he raised objections to key parts of the Constitution, especially one particular omission: “Let me add that a bill of rights is what the people are entitled to against every government on earth, general or particular, and what no just government should refuse or rest on inference.” Jefferson’s insistence on a bill of rights echoed the position of George Mason, another close friend, who was at that moment arguing that delegates like Madison were attempting to establish a “modern aristocracy” without regard for “the people.” Jefferson agreed with Mason that it was only through a bill of rights that liberty could be preserved and tyranny avoided.

Madison disagreed; he opposed making the inclusion of a bill of rights the precondition for ratification, as his friend suggested. He doubted that mere “parchment barriers” could protect against encroachments on liberty, and they might even encourage the government to violate any rights not explicitly mentioned. After all the hard work he had invested, Madison felt convinced that the way he had structured the Constitution was plenty sufficient to protect individual rights.

But Jefferson would not relent, even if he had to operate from the sidelines. He began searching for outlets that would circulate letters—written by him but without his name attached—stressing the necessity of a bill of rights. When Patrick Henry heard that Jefferson’s letters were making the rounds, he seized the chance to sow more discord and impede ratification in divided states. At the Virginia Ratifying Convention, Henry invoked Jefferson’s name in an attempt to discredit the Constitution: “This illustrious citizen advised you to reject this government till it be amended.” Henry knew full well what embarrassment and inner conflict this announcement would cause for Madison. During the debates, though, Madison betrayed no ill will, insisting that he knew better than anyone where Jefferson’s true feelings lay: “I believe that were that gentleman now on this floor, he would be for the adoption of this constitution.”

Outwardly, they maintained their First Friend status. Deep down, however, Madison bristled at Jefferson’s covert maneuvering, which might have contributed to his decision to keep his own secret as well. Without telling Jefferson, he had begun working in the fall of 1787 on The Federalist Papers with Hamilton and John Jay, a project that would become famous for its eloquent defense of the Constitution. Not until a year later, a mere two months before its official publication, did Madison mention the Federalist Papers to Jefferson.

Though Jefferson had heard about the Papers from other participants, he respectfully waited for Madison to reveal the news to him directly. And when Madison finally did, Jefferson responded graciously, with admiration and pride for the feat Madison had accomplished: “I sincerely rejoice at the acceptance of our new constitution.” Jefferson still insisted that the key element in need of “retouching” was a bill of rights, that “half a loaf is better than no bread.” But he knew to tread lightly at this delicate point in their friendship.

Perhaps Jefferson also knew that Madison’s pragmatism would ultimately prevail and that he would see the merit in a bill of rights. Though initially wary of doing anything that might throw ratification into doubt, Madison eventually came around to his friend’s view after realizing he needed to show flexibility to win his race for Congress against his friend James Monroe. Having suffered the indignity of losing a Senate seat to two anti-Federalists in an earlier vote of the Virginia state legislature, Madison could ill-afford to lose another race now for the House. Nor could he deny any longer that constitutional revisions would be necessary to placate anti-Federalist opposition; unity, he concluded, would be better than perfection. So he ran for the House in part on support for a Bill of Rights—and won easily. On June 8, 1789, fulfilling his campaign promise, Madison proposed a series of constitutional amendments to be considered by the First Congress. When ten of those were finally ratified, Madison became widely hailed as “the Father” not only of the Constitution but also of the Bill of Rights.

The pivotal years of drafting the Constitution and Bill of Rights could have marked the first serious rupture between Madison and Jefferson. What preserved their friendship was their mutual awareness that the Constitution was far from finished in 1789. In a sense, their ability to come to an agreement about the Constitution stemmed from an understanding that their own friendship operated in a similar fashion. Just as Madison calmed Jefferson’s idealism and Jefferson inspired Madison’s, so too did America have to strike the proper balance between self and society, unrestrained freedom and political order.

Considering how fully the Madisonian and Jeffersonian worldviews differed in 1789, it is shocking how quickly things would change, a testament to the tectonic shifts occurring across the American landscape. In what would be the greatest plot twist of all, Madison—in less than a year—would become the most ardent Jeffersonian of his era.

After five years in France, Jefferson returned home to a fractured nation. Insiders expected him to plunge right back into the political storm, especially given his recent drive to influence the Constitutional Convention from afar. But Madison knew his friend and what motivated him better than anyone. He appreciated fully Jefferson’s persistent streak of domesticity and how it would pull him back to Virginia. Even before Jefferson landed on American shores, Madison had tried gauging his interest in accepting an appointment in Washington’s administration. Jefferson stalled, claiming that his sole “object is a return to… retirement.” But Madison wasn’t deterred. Shortly after Jefferson’s arrival, Madison visited him at Monticello to goad him back into public life, just as he had done after Jefferson’s humiliation as Virginia governor and Martha’s tragic death. Madison’s persuasiveness prevailed once again. A few months later, Jefferson found himself living at 57 Maiden Lane in New York, poised to negotiate the momentous Dinner Table Bargain.

With that extravagant and carefully orchestrated meal, Jefferson and Madison signaled the rebirth of their “great collaboration,” now mightier than ever. But that collaboration was so durable in 1790 precisely because of the preceding years of divergence. Only by working through their differences over the Constitution and Bill of Rights could Madison and Jefferson emerge stronger in their conviction of what they held in common.

The simplistic explanation for Madison’s conversion is that Jefferson simply won him over once back in America. But that explanation does a disservice to Madison’s independently brilliant mind—and his deep-seated resolve to prove himself equal to his famous friend. By the time Jefferson returned from France in September 1789, Madison had vastly matured. He had spent the last five years in the weeds of policy making, confirming his bona fides as an impressive statesman and a supreme intellectual. He was no longer just Jefferson’s admirer or student; he was a veteran of the constitutional battles of the 1780s. Few other Revolutionary leaders possessed as sophisticated an understanding of the new American republic and its levers of power as did Madison. Any evolution in his thinking arose from his own considered judgment, with Jefferson providing some—but far from all—of the influence.

In the six months prior to the fateful dinner on Maiden Lane, Madison had already begun moving closer to Jefferson. The key moment came in January 1790, when Hamilton submitted his First Report on the Public Credit to Congress. The report outlined Hamilton’s fiscal goals, which echoed Madison’s own arguments at the Constitutional Convention and in The Federalist Papers. In fact, before 1790, Madison had collaborated far more with Hamilton as a nationalist than he had with Jefferson. It was actually Madison who had first promoted the assumption of state debts in the 1780s—now a key tenet of Hamilton’s fiscal proposal. It was Madison who had joined with Hamilton under the pseudonym “Publius” to write The Federalist Papers. And it was Madison who had proven to be the most outspoken defender at the Constitutional Convention for a powerful national government.

But now, in Madison’s words, “I deserted Colonel Hamilton, or rather Colonel H. deserted me.” After considering Hamilton’s fiscal plan more deeply, Madison feared the prospect of the federal government exercising economic control over all thirteen states, including his beloved Virginia. In his view, this consolidation of power would not just pervert the legacy of the Revolution; it would translate to economic advantages for a narrow subset of the population centered in the northeast. Both Madison and Jefferson, despite their privileged backgrounds, believed they represented the common man: yeoman farmers who formed the basis of republican decency and agrarian society. Hamiltonian Federalists, in their eyes, were Anglophiles who protected the financial interests of merchants, bankers, businessmen, and other members of the urban elite. So as nationalism surged under Federalist rule, Madison found himself inching closer to his roots, ones that his best friend had never relinquished.

The new rift between the two friends and Hamilton defied expectations, as the three had been expected to form a fierce trio within Washington’s unofficial Cabinet (officially Madison was a US congressman from Virginia). But Madison and Jefferson quickly realized that they were outliers in the administration, with the president increasingly swayed by Hamilton’s recommendations, especially the establishment of a national bank. As tensions escalated, Jefferson sarcastically told Washington, “Mr. Madison and I have wondered whether we should resign, since Mr. Hamilton is taking over both our jobs.” Such not-so-subtle hints did little to diminish Hamilton’s influence; the Federalists steadily secured most of Hamilton’s pet causes. Jefferson—who often recoiled from conflict—seemed overwhelmed by the fight ahead, confessing to Madison, “Hamilton is really a colossus.” But he now had a fierce ally on his side. He recognized how resilient the soft-spoken, diminutive Madison truly was, and how potent their combination could be in checking Hamilton’s worst abuses. In one letter to Madison, Jefferson praised his tireless commitment to undermining their mutual foe: “There is nobody but yourself who can meet him.”

Their relationship during this period reached new heights. They schemed and strategized, and in between dined and mused generally about life. In one letter Jefferson deigned “to make a proposition” to Madison “… to come and take a bed and plate with me. I have four rooms of which any one is at your service. Let me intreat you, my dear Sir, to do it, if it be not disagreeable to you. To me it will be a relief from a solitude of which I have too much.” He even touted the advantages of his vast library to further entice his friend.

Madison declined the lodging offer, but he did agree to a second proposal from Jefferson to take a vacation. In May 1791, they embarked on a month-long trip through New England and upstate New York, looking for, in Madison’s words, “health, recreation and curiosity.” They spent most of their time studying plants, fishing, and wandering over Revolutionary War battlefields.

But even on this supposed vacation, they couldn’t refrain from politicking. Privately, they met with anti-Federalist leaders, including the newspaperman Philip Freneau, a classmate of Madison’s from Princeton. The two friends were consciously strengthening their coalition and beginning to breathe life into a formidable new force: the Democratic-Republican Party (a faction of which later became today’s Democratic Party). By October 1791, they had persuaded Freneau to help establish a mouthpiece for their fledgling party—the National Gazette newspaper, an obvious counterweight to Hamilton’s own Gazette of the United States.

The catch was that Jefferson, as secretary of state, was using the National Gazette to launch a mud-slinging campaign against the very administration he still worked for. So he had to find ways to be as discreet about his involvement as possible. Rather than writing articles for the press himself, he recruited Madison to do much of the dirty work. In a letter on July 7, 1793, he urged Madison to go on the offense: “For god’s sake, my dear Sir, take up your pen, select the most striking heresies, and cut him to pieces in the face of the public.” Madison willingly obliged, penning a series of scathing articles signed with the name “Brutus.” These dynamics foreshadowed the nature of their alliance for the next two decades, with Madison often working behind the scenes and Jefferson trying to float above the fray.

Still, Jefferson could not avoid the emotional wear of statecraft. By December 1793, he had grown so worn out from constantly battling Hamilton that he resigned from Washington’s Cabinet and retired to Monticello. There, he focused on developing a crop rotation system and also established a nail factory operated by his teenage slaves. But just as in the past, Jefferson’s quasi-farmer life masked the fact that one foot still remained in politics—with Madison as his vital link. In fact, Jefferson now found it even more advantageous to exert influence from outside the administration, and Madison as always was his willing accomplice.

In a letter to Jefferson during his brief retirement, Madison divulged personal news that delighted his best friend: He had at last shed the embarrassment of his “single state” by marrying the vivacious, twenty-three-year-old widow Dolley Payne Todd. Jefferson already knew of the romance and approved. Ten years after having his heart broken by a teenager, Madison at forty-three had finally found his life partner. But in a nod to his equally important alliance with Jefferson, he was careful to note that marriage would not in any way interfere with their business, adding: “I shall always receive your commands with pleasure.” In that same letter, Madison hinted at his own interest in retiring, but Jefferson wouldn’t hear of it: “But this must not be, unless to a more splendid and more efficacious post.” Unless Madison were considering running for president, Jefferson implied, he must not entertain any ideas other than remaining as leader of the opposition party. So over the next several years, with guidance from Jefferson, Madison worked within Congress to strengthen the young party and sharpen its platform.

Jefferson’s semi-absence from politics did not last long. At first, he uttered his usual protestations when Madison urgently wrote in March 1795 that he should seek the presidency: “You ought to be preparing yourself… to hear truths which no inflexibility will be able to withstand.” The fifty-one-year-old Jefferson responded that he had no such interest, despite rampant rumors that he aimed to succeed Washington. “The little spice of ambition, which I had in my younger days,” he claimed, “has long since evaporated.” Years later, however, Jefferson admitted that his attempt at permanent retirement left him a shell of his former self. From the confines of Monticello, he realized how fully politics formed the core of his being: “From 1793 to 1797 I remained close to home, saw none but those who came there, and at length became very sensible of the ill effect it had upon my own mind.… I felt enough of the effect of withdrawing from the world then, to see that it led to an antisocial and misanthropic state of mind, which severely punishes him who gives into it: and it will be a lesson I shall never forget as to myself.”

Thus, by December 1796, in a stunning turnaround, Jefferson returned to politics as the standard-bearer for the Democratic-Republican Party—and Madison again played the role of his shrewd operative, charting Jefferson’s political comeback. In those days, electors didn’t vote for tickets, and candidates for president did not select a running mate. Instead, before the 12th Amendment was ratified in 1804, the system provided for each state elector to cast two votes, not distinguishing between president and vice president. The candidate with the most electoral votes would then be declared president, with the runner-up becoming vice president. The election of 1796 thus was the first truly contested election in American history after George Washington refused to run for a third term, pitting two parties against each other: the Federalist candidates John Adams and Charles Pinckney against the Democratic-Republican candidates Jefferson and Aaron Burr. The Constitution thus made it possible for two leaders of opposing parties to serve concurrently as president and vice president. As Jefferson worried over the possibility of not winning the presidency, Madison advised him to accept whatever came to pass: “You must reconcile yourself to the secondary as well as the primary station, if that should be your lot.” And when Jefferson did finish a close second in the election, he eventually swallowed his pride and agreed to serve under his bitter rival, Federalist president John Adams.

Working together in the same administration only worsened the divisions between Adams and Jefferson and their respective parties, as became obvious in June 1798, when the Federalist-dominated Congress passed the Alien and Sedition Acts. One of the most controversial aspects of the Acts made it illegal to criticize the government’s policies in its impending war against France. Not coincidentally, this meant that prosecutions were targeted primarily at newspaper editors favoring Jefferson and Madison’s new party, the pro-French Democratic-Republicans.

For Jefferson, such prosecutions amounted to a “reign of witches,” with Federalists exercising monarchical powers to suppress free speech and press. Meanwhile, Madison had recently retired from Congress, tired of the constant infighting and deflated by what he viewed as Federalism’s constitutional abuses. After twenty-three years in public service, he was enjoying life at Montpelier as a gentleman-farmer. But the uproar over the Acts—which Madison denounced as “a monster that must for ever disgrace its parents”—roused him back to action.

While both deplored the Alien and Sedition Acts, the friends did not blindly agree on how to undercut them. In October 1798, Jefferson invited Madison to Monticello and showed him drafts of what would become known as the Kentucky Resolutions. Jefferson’s resolutions made a radical argument (though toned down when adopted later by the Kentucky legislature): that the Acts were “void” and that states could “nullify” such unconstitutional laws. In effect, Jefferson repudiated the belief that the president, Congress, or the Supreme Court were the final arbiters of constitutionality.

Madison, of course, did not fully agree—even though he had been inching closer to a states’ rights position over the last decade. A month after meeting with Jefferson, Madison wrote his own Virginia Resolutions, which employed more restrained language to argue for the right of states to announce that a law was unconstitutional but not the right to nullify a law outright. Under Madison’s purposefully vague language, states could “interpose” against the Acts using all “necessary and proper measures” to protect their rights, but they couldn’t consider the Acts utterly “void & of no force.”

Such fine distinctions, however, were papered over amid the country’s heightened polarization. Despite Madison’s conciliatory language, seven state legislatures rejected both the Kentucky and Virginia Resolutions, with three issuing condemnations over the threat the Resolutions posed to the Union. Still, the outcry over the Alien and Sedition Acts persisted, with the Adams administration plagued by accusations of federal overreach. Amid this continued opposition to the Acts, Jefferson’s and Madison’s Resolutions did serve as useful campaign documents, helping rally together Democratic-Republicans just in time for the presidential election of 1800.

After nearly a decade of consolidating their Democratic-Republican forces, the two friends could finally rejoice when the so-called “Revolution of 1800” ushered in a major political realignment, with vice president Thomas Jefferson defeating incumbent president John Adams. This win occurred only after the House of Representatives cast thirty-six ballots to determine whether Jefferson or his running mate, Aaron Burr, who both received the same number of electoral votes, would become president. Ironically, it was none other than Hamilton who played the decisive role in throwing his support behind Jefferson, viewing him as the lesser evil. On March 4, 1801, Jefferson became the first president to take the oath of office at the new capital on the Potomac, the prize he had secured from the Dinner Table Bargain over a decade before (although not the first to reside in the White House, as Adams had beaten him by four months). One of his first decisions as president was to appoint Madison as secretary of state.

In his inaugural address, carefully edited by Madison, Jefferson ironically sought to heal the same political wounds that he had helped stoke throughout the 1790s. Glossing over the animosity of the previous decade, Jefferson proclaimed: “We are all republicans; we are all federalists,” evoking a theme candidates would use to great effect for the next 220 years. Aside from being a call for unity, those words carried another layer of unintended meaning. Jefferson and Madison would soon discover how much they, when faced with the realities of power, acted like the Federalists they had once condemned. Both men ended up overturning few of the institutions they had criticized in the 1790s. Even Hamilton’s prized national bank, the source of so much discord during the Dinner Table Bargain, remained untouched. Yet again, the “checks and balances” in their own friendship provided a fitting guide for how to act as presidents: accommodating their seemingly fixed principles to circumstance and experience.

The most striking illustration of the necessity for compromise occurred midway through Jefferson’s first term. During debates over the Constitution, Jefferson had proudly told Madison that he was no fan of “energetic government.” But in 1803, he pulled off one of the most energetic uses of federal power ever: the historic Louisiana Purchase from France, doubling the size of the nation with 827,000 square miles of land west of the Mississippi River. In October 1802, that vast region had come under French control after Napoleon Bonaparte reached an agreement with Spain’s King Charles IV. Jefferson and Madison viewed that agreement as a crisis in the making. After his time abroad, Jefferson was more than familiar with France’s imperial ambitions, and he worried about the military dangers of that country controlling the Mississippi River.

He and Madison worked feverishly to try to resolve this issue through diplomatic channels, but the Federalist Party increasingly clamored for war. Fearing the prospect of disunion, Jefferson recognized the need to take more visible action than just backroom maneuvering with Madison. So in January 1803, he enlisted his political ally James Monroe to join Minister to France Robert Livingston in an attempt to acquire some of the Louisiana territory from Napoleon. Before Monroe’s departure, Jefferson told him (no pressure): “All eyes, all hopes, are now fixed on you,… for on the event of this mission depends the future destinies of this republic.” Monroe’s instructions, written by Madison and approved by Jefferson, allowed up to $10 million to be spent on New Orleans and all or parts of the Floridas.

When Monroe reached Paris on April 12, however, the political equation in France had already changed. Napoleon’s grand scheme to reestablish French presence in the New World had started to unravel after a rebellion of slaves and free Black persons in Saint Domingue (now Haiti). Even worse, a new war with Britain appeared unavoidable. France’s treasury minister, François de Barbé-Marbois, advised Napoleon that Louisiana would be rendered worthless without Saint Domingue and that France would likely lose the territory in the event of war with Britain. Reluctantly, Napoleon concluded his best option was just to sell the territory, and that was what he did, for $15 million. Including New Orleans, it was a stretch of land that would ultimately encompass fifteen states. It was, as Jefferson later described, “a fugitive occurrence”—such a steal that in today’s dollars it equates to less than fifty cents an acre—something beyond both his and Madison’s wildest dreams.

The deal was officially announced on July 4, 1803, a day for Americans to celebrate not just their independence from Britain but their tangible progress toward world influence. The deal was not universally popular, though. Ironically, it was the Federalists who continued to ramp up their criticism of Jefferson, arguing that purchasing such a huge expanse from a foreign government was not allowed under the Constitution. The Federalists were certainly correct in the most literal sense: The Louisiana Purchase did clearly test Jefferson’s principles, forcing him to expand his strict interpretation of the Constitution and his idealistic pronouncements on limited federal power. He admitted as much to Livingston: “Perhaps nothing since the Revolutionary War has produced more uneasy sensations through the body of the nation.”

Jefferson tried to sidestep Federalist criticisms by proposing a constitutional amendment that would allow for the government to purchase and incorporate new territory into the Union. In other words, since a provision for this particular power didn’t exist, it could be written in—and Jefferson could still claim to be adhering to the Constitution’s plain words, not overstepping his bounds. Madison, however, disagreed about the need for such an amendment, reverting to his earlier flexibility over what the Constitution permitted under its treaty-making provisions. Once again, Jefferson was left persuaded by his friend, agreeing that they needed to push for ratification now, before the deadline passed.

Heeding Madison’s advice, the president rationalized the position of the Democratic-Republicans—now suddenly supportive of broad presidential powers—in his usual sentimental, slightly exaggerated terms: “It is the case of a guardian, investing the money of his ward in purchasing an important adjacent territory; and saying to him when of age, I did this for your good.” With those paternalistic words, Jefferson and Madison managed to overcome Federalist opposition and convince Congress to ratify and fund the Louisiana Purchase. After only two days of debate, the Senate approved the treaty by a vote of 24 to 7, and it was signed shortly thereafter.

The Louisiana Purchase was as much a political triumph for Madison as it was for Jefferson. As Jefferson’s chief advisor, Madison supervised the entire transaction, with French Foreign Minister Charles Talleyrand noting that it was the inhibited Madison who actually “governed the President” in foreign affairs. Madison also played a chief role in ensuring that a durable Senate majority would pass the Louisiana Treaty, making it more immune to criticism. And for the next six years, he would continue to stick with Jefferson, as new events unfolded that challenged much of what they professed to believe.

With successes like the Louisiana Purchase, Republican ideas soon gained sway over national politics. In response, opponents decided that one of the easiest ways to weaken Jefferson’s popularity was to dig up the sordid details of his private life—which inevitably involved Madison. Because Madison and Dolley lived with Jefferson in the White House at the beginning of his term, stories began circulating that the president had commenced a sexual relationship with his best friend’s wife. Added to that incendiary (and false) claim was the more accurate charge that Jefferson had fathered several children with his slave Sally Hemings.

Both these accusations also converged into an even more twisted reality: On January 18, 1805, Sally gave birth to a son who would be named James Madison Hemings. Dolley, present at Monticello for the birth, pled Sally for the honor of naming the baby after her husband in exchange for a “fine present.” Sally agreed—but no present ever arrived. And a year later, Martha Jefferson Randolph, one of Jefferson’s daughters with his deceased wife, gave birth to her own son and also named him James Madison Randolph. It was this type of intimate (if perverse) connection—Jefferson’s slave son and free grandson, both named after Madison—that illustrates the complex layers sustaining their legendary political partnership.

Naturally, then, after Madison won the overwhelming support of Republican congressmen to be their presidential nominee in 1808, the election emerged as a referendum on Jefferson’s own stewardship of the nation. In attempting to discredit Madison, the Federalists repeated their familiar criticisms of Jefferson: that Madison was a Francophile; that the Virginians exercised far too much control over national politics; that the Democratic-Republican fear of centralized power encouraged mob rule. None of those arguments worked. Madison secured 122 electoral votes over Federalist candidate Charles Cotesworth Pinckney’s meager 47—and now followed his friend in becoming president of the United States.

On March 4, 1809, Jefferson cheerfully attended Madison’s own presidential inauguration, sitting alongside his comrade at the front of the Capitol hall. When it came time for Madison to deliver his inaugural address, the newly sworn-in president could barely contain his nerves. But he managed to pull himself together, conscious of the fact that his election represented an endorsement of Jefferson’s own vision. As the writer (and contemporary observer) Margaret Bayard Smith recalled, “Mr. Madison was extremely pale and trembled excessively when he first began to speak, but soon gained confidence and spoke audibly.” As his friend listened proudly, Madison delivered a short but clear speech announcing his intention to continue governing with Jeffersonian principles.

During that evening’s ball in Long’s Hotel, someone remarked on how happy Jefferson looked in comparison to his solemn successor, as if Jefferson “were the one coming in, and he the one going out of office.” Jefferson replied, with more than a little relief: “There’s good reason for my happy and his serious looks. I have got the burden off my shoulders, while he has now got it on his.” For Jefferson, the presidency would soon be a distant memory. At long last, he could spend the rest of his days in Virginia as “the Sage of Monticello.” But part of his happiness also arose from seeing Madison in this new, glorified light, as Smith wrote: “I believe… that every demonstration of respect to Mr. Madison gave Mr. Jefferson more pleasure than if paid to himself. I do believe father never loved son more than he loves Mr. Madison.”

As the festivities ended and Madison entered the White House, he faced an uncomfortable fact: His dear friend and predecessor had left him with an impending war on his hands. Back in 1807, Jefferson and Madison had imposed a trade embargo against Britain and France as a way to stay out of their ongoing war. Incensed by this policy of neutrality, the two European countries had begun attacking American ships. Ultimately, the embargo ended up harming American sailors and merchants more so than it did Europe. So shortly before leaving office in 1809, Jefferson lifted the embargo. But hostilities still simmered. On his way back home, Jefferson wrote a letter to the new president, acknowledging this tricky situation: “If peace can be preserved, I hope and trust you will have a smooth administration.” Aiming to ease Madison’s stress and affirm his continued support, Jefferson concluded his letter with a heartfelt expression: “I salute you with sincere affection and every sympathy of the heart.”

It was a touching note, but it could do nothing to stave off reality: Madison was about to have anything but a “smooth administration.” Soon after he took office, the British navy continued its aggression, reneging on a peace agreement and then forcing American sailors pulled from seized ships to serve on its behalf in its war against France. From Monticello, Jefferson watched in horror as one of his greatest fears—British power over America—loomed once again. Though he hoped that armed conflict with Britain could be avoided, he also advised Madison to prepare for the worst. On November 5, 1811, the president sent his war message to Congress, urging the nation to defend its hard-fought independence. Jefferson responded with tender words of encouragement: “Your message had all the qualities it should possess, firm, rational, and dignified.… Heaven help you through all your difficulties.” Those words arrived just in time: Before his first term ended, Madison found himself the nation’s first wartime president. His presidency—not to mention the future of the embryonic country—rested on him winning what he soon dubbed “our second war of independence.” For all the rousing rhetoric of Madison’s war declaration, the truth was that the nation was far from ready for war. Congress had not provided sufficient funds or other necessities for a standing army, while several states blasted “Mr. Madison’s War” as a foolish exercise and refused to contribute their militias. American forces attempted to fight back on land and sea, but the ordeal proved to be a grueling and unpopular one. As war raged throughout 1812, Madison managed to win re-election over Federalist candidate DeWitt Clinton, but he still faced a barrage of criticism over the international debacle. At one point, New England even threatened to secede from the Union.

By 1814, the war looked all but lost. British troops stormed into DC, ransacking the city while laying waste to the White House. Dolley Madison stayed behind at the mansion just long enough to save Gilbert Stuart’s famous painting of George Washington. Only after General Andrew Jackson won a resounding and unexpected victory over the British in the Battle at New Orleans in early 1815 could Americans finally rejoice; they had won a second War of Independence over their bitter adversary.

Madison left office in 1817 more popular than he had arrived, so successful that his former enemy John Adams was forced to acknowledge that Madison had “acquired more glory, and established more union, than all his three predecessors, Washington, Adams, and Jefferson, put together.” Jefferson himself agreed with Adams’s assessment, writing after the signing of the Treaty of Ghent, which ended the war, that “the cement of the Union is in the heartblood of every American.” There could be no better evidence of shared historical purpose for Jefferson: that the presidency of his beloved First Friend marked the end of half a century of hostilities with Britain, thus ensuring a more perfect Union.

Jefferson and Madison’s friendship was defined not just by the boisterous times but by the calmer ones, the moments when they withdrew from the swirl of politics and immersed themselves in books, walks, and lighthearted conversation. In retirement, they launched one final collaboration: establishing the University of Virginia. The university fulfilled Jefferson’s lifelong dream of founding an academic temple dedicated to letters and science. As always, Madison stood loyally by his side, helping to hire the faculty and prepare books for the library.

For years, Jefferson had struggled to secure funding for the university, a struggle that would then be echoed in his own finances. In February 1826, he was forced to sell all of his property except for Monticello due to financial difficulties. He used the poignancy of the moment to write his best friend about the depth of his gratitude amid such great loss: “The friendship which has subsisted between us, now half a century, and the harmony of our political principles and pursuits, have been sources of constant happiness to me throughout that period.” After that emotional note, the friends saw each other one last time, at the university’s Board of Visitors meeting in April. Jefferson died a few months later on July 4, the fiftieth anniversary of the Declaration of Independence and of his friendship with Madison. In his will, Jefferson gifted Madison a gold-headed walking stick, which Jefferson considered “the most elegant thing… I have ever seen.” Both men understood the symbolism of such a gift. As Jefferson had written to Madison that February, “You have been a pillar of support through life. Take care of me when dead, and be assured that I shall leave you with my last affections.” And Madison did take care of Jefferson after death, serving as rector of the university, as well as guarding Jefferson’s sterling reputation when speaking to biographers and historians.

Madison, who as a sickly young man had always predicted his imminent demise, ultimately outlived most of his contemporaries. In June 1836, Dr. Robley Dunglison, Jefferson’s personal physician, traveled from Baltimore to attend to the ailing Madison. Dr. Dunglison offered him stimulants to extend his life until July 4, so that he could die on the same day as Jefferson a decade later. As much as he was tempted to share one final thing with his friend, Madison refused.

After his burial at the family plot in Montpelier, Madison’s family released a note he had written entitled “Advice to My Country.” With Jeffersonian eloquence, the small man with the quiet voice now articulated his dying wish for the republic—the core truth that transcended whatever once separated the two partners:

“The advice nearest to my heart and deepest in my convictions is that the Union of the States be cherished and perpetuated.”