Roosevelt’s boots had hardly touched the pier at Montauk before he was repeatedly told he would be the next governor of New York after the oncoming election, five months away. “Should I run?” he asked Lincoln Steffens. Steffens told him yes and said he would win.

Both men knew the race would be complicated. The nomination was controlled by Senator Thomas Collier Platt, the undisputed leader of the state’s Republican Party. Platt’s label as the “easy boss” belied his ruthless treatment of anyone who opposed him. Platt had collided with Roosevelt both when the would-be governor was civil-service commissioner, and Platt was trying to preserve patronage jobs, and when he was police commissioner and Platt was protecting his cronies.

If Platt let Roosevelt become governor, the two would clash over the candidate’s reform principles and growing revulsion at the abuses of robber barons, who provided the money that funded Platt’s power. But Roosevelt was the hero of San Juan Hill and the most famous man in America; given the GOP nomination, he could sweep the state. His chances looked so good that Roosevelt considered an offer to run on an independent ticket, gambling that Platt would have to offer him the GOP nomination as well. In the end, he rejected that tactic, reasoning that he would need the party’s backing to work with the legislature after he was elected.

After a series of delicate negotiations, Roosevelt showed up in mid-September at Platt’s headquarters in the Fifth Avenue Hotel. Emerging from a long meeting, he started to say, “I had a very pleasant conversation.” Then a reporter shouted, “Will you accept the nomination for governor?” “Of course I will!” said Roosevelt. “What do you think I am here for?” What’s more, he said, he would not accept an independent nomination.

The independents felt betrayed, reformers suspected a deal had been struck, and Democrats exclaimed the hero had surrendered to the boss. “Rough Rider Roosevelt made a charge up the backstairs of the Fifth Avenue Hotel,” said a Democratic newspaper, but this time, “he was taken prisoner.” The next day, after a long private talk with Roosevelt, Steffens reported in his Commercial Advertiser that there had been no deal. Roosevelt, he said, made the decision on his own to make sure he would have a majority in the legislature to carry out his program.

That account didn’t reassure everyone, and the campaign got off to a difficult start, with many of Roosevelt’s allies remaining silent. Candidates in those days rarely stumped for themselves, but Roosevelt saw it as a viable strategy – and so, in the end, did Platt. In the final weeks, Roosevelt’s campaign train crossed the state, and he attracted large crowds at every stop. “The fire and school bells rang,” said The New York Times. “Cannon fired and a band played, while the people cheered.” Two Rough Riders Accompanied Roosevelt. In an effort to be discreet, they wore civilian clothes, but the people who gathered to see the candidate were eager to hear their stories of Roosevelt’s courage. Sergeant Buck Taylor of Cripple Creek, Colorado, gave this endorsement: “I want to talk to you about mah Colonel. He kept ev’ry promise he made to us and he will to you . . . . He told us we might meet wounds and death and we done it, but he was thar in the midst of us, and when it came to the great day he led us up San Juan Hill like sheep to the slaughter and so he will lead you.”

This, Roosevelt said later, “hardly seemed a tribute to my military skill, but it delighted the crowd, and as far as I could tell did me nothing but good.” The Roosevelt campaign train chugged on. The candidate delivered as many as nineteen speeches a day and often made impromptu comments at whistle-stops.

Roosevelt won the election by just 18,000 votes – far short of a landslide, but a triumph for his party. Even Boss Platt conceded that only Roosevelt could have won the race.

The new governor was forty years old when he took office on a bright January day so cold the band’s brass instruments were frozen and unplayable. Edith was settling the family into the forty-room governor’s mansion in Albany. She hired a governess for fifteen-year-old Alice; enrolled Theodore Jr., twelve, and Kermit, ten, in a local boy’s academy; set up a schoolroom in the basement for Ethel and Archie, ages eight and five; and a nursery for Quentin, still a toddler. Edith dreaded the social obligations that came with her new role as a governor’s wife, but she welcomed the financial security that came with the office. In addition to the mansion, the governor’s job brought a salary of $10,000, and Roosevelt’s celebrity ensured increasing sales for his writing; his forthcoming memoir, The Rough Riders, was set to be serialized at $1,000 per installment. As time passed, Edith made friends and began to enjoy state politics, especially meeting New Yorkers at county fairs and village meetings.

Roosevelt had promised to be loyal to Platt and the GOP, but never to put the party ahead of the good of the people. Progress, he believed, could only be made through compromise and practical politics. He traveled to Manhattan every weekend to confer with Platt, a pilgrimage that infuriated ardent reformers of what Roosevelt called “the tom-fool variety” who saw any contact as a betrayal. After an early clash with Platt when the boss tried to dictate a key appointment, the governor engineered a compromise: When an appointment was to be made, he would present Platt with a list of acceptable candidates, and Platt could choose the winner.

As he had throughout his career, Roosevelt cultivated the press as a direct conduit to the public. In addition to a weekly meeting with Steffens during his visits to Manhattan, the governor continued to correspond with such influential writers as Ray Stannard Baker and William Allen White. He enlisted H. H. Kohlsaat, publisher of the Chicago Times-Herald and a McKinley adviser, to critique drafts of his speeches. And he befriended humorist Finley Peter Dunne, whose irreverent Irish bartender character Mr. Dooley was a prominent political commentator. When Mr. Dooley quipped that The Rough Riders should have been called Alone in Cuba, Roosevelt wrote that his family and friends were “delighted with your review” and invited him to visit. Dunne became a friend but kept sniping. “I never knew a man with a keener humor or one who could take a joke on himself with a better grace,” he wrote. Roosevelt proved the point by telling often of a young lady who told him at a reception her favorite of his books was “that one, you know, Alone in Cuba.”

The new governor also announced that he would hold two press conferences every day he was in Albany. He was candid in these gatherings, sharing jokes and gossip, explaining his goals, and indicating when he was going off the record. The twenty-five regular statehouse reporters cherished his confidences and were quickly won over by his candor, command of the issues, and what one of them called “the wonderful mental activity of the man.”

Reprising one of the strategies he employed as an assemblyman, Roosevelt recruited Jacob Riis to escort him on a tour of tenement sweatshops, this time to dramatize the way state laws regulating working conditions were widely ignored. After finding predictably appalling scenes from cellar to garret in twenty buildings, Roosevelt confronted the state’s factory inspector, insisted on reforms, increased the number of enforcers, and began pushing a bill to revise the code. Working against his party’s grain, he would ultimately succeed in passing policies that included an eight-hour work day for state employees, limiting working hours for women and children in private industry, and improving working conditions for children.

Roosevelt was similarly successful in passing conservation measures. Working with Gifford Pinchot, head of the U.S. Forestry Division, Roosevelt persuaded the legislature to create the Palisades Interstate Park on the Hudson River, to preserve tens of thousands of acres of woodlands in the Adirondack and Catskill mountains and to take measures protecting endangered songbirds.

Perhaps inevitably, Roosevelt’s cordial relations with Platt foundered on an issue of principle. For all his experience in the Assembly, Roosevelt hadn’t entirely understood the complicated connections between Platt’s machine and the corporate world. Unlike most political bosses, Platt wasn’t out to enrich himself; his goal was political power, but he amassed it by collecting corporate contributions, which he could dole out to legislators on the understanding they could be counted on to vote in accordance with the donors’ wishes. When Governor Roosevelt embraced the idea that corporations that received exclusive franchises from the state should pay taxes in return, he was astonished to meet “a storm of protest and anger” from Boss Platt.

Franchises for lucrative telephone and telegraph networks, electric street railways, and similar ventures had been granted for years, often through outright bribery. To Roosevelt, it was “a matter of plain decency” that the beneficiaries should pay taxes for privileges worth billions of dollars. He set out to resurrect a franchise-tax bill that had been introduced by Democratic state senator John Ford and left to languish in committee. At their next breakfast meeting, a furious Platt warned the governor that this “radical” bill would never pass. Roosevelt thought it was flawed - but better than no bill at all - and managed to get it through both houses of the legislature. When the Assembly speaker followed Platt’s order and killed the bill on the final day of the session, Roosevelt invoked a Special Emergency Message to force it to the floor, where it passed.

In a bitter letter, Platt warned the governor, “You will make the mistake of your life if you allow that bill to become a law.” Once again, Roosevelt chose to compromise. Since “you have treated me so well and shown such entire willingness to meet me halfway,” he told Platt, he would call a special legislative session to consider amendments to the bill. However, he warned, if the law was weakened, he would sign the original bill. The session resulted in two improvements: Instead of letting cities determine the tax rates, the bill established a department of state assessors, and a company could deduct any taxes it had already paid from new levies. Hailing these as “just and reasonable” measures, Platt endorsed the bill.

But there was another bitter point of contention between the governor and the boss. The state’s superintendent of insurance, Lou Payn, was a crony of Platt’s but also maintained close relationships with the companies he was supposed to oversee. As Payn’s three-year term neared an end, Roosevelt announced he wanted to appoint a new superintendent. Again Platt erupted, reminding the governor that the Senate, which Platt controlled, had to approve any replacement. Reverting to a tactic that had been successful months earlier, Roosevelt offered a list of candidates, telling Platt to choose one. Platt refused to consider any candidate but Payn, who was not on the list. Scandal failed to break the impasse. Evidence emerged showing Payn received $435,000 in suspect loans from the State Trust Company of New York. Despite the charges, Platt threatened “war to the knife” if Roosevelt persisted in his efforts to dismiss Payn. Roosevelt offered to appoint Francis J. Hendricks, a favorite of Platt’s. Platt refused.

In a meeting between the governor and Platt’s top lieutenant, Benjamin Odell, Odell told Roosevelt his reputation would be destroyed if he defied Platt. Roosevelt said there was no point in further talk.

“You have made up your mind?” Odell asked.

“I have,” Roosevelt replied.

“You know it means your ruin?”

“Well, we will see about that,” Roosevelt said as he pushed away from the table and walked away.

“You understand, the fight will begin tomorrow and will be carried on to the bitter end.”

“Yes,” Roosevelt retorted as he opened the door. “Good night.”

“Hold on! We accept. Send in Hendricks.”

In his Autobiography, Roosevelt reflected: “I never saw a bluff carried more resolutely to the final limit.” But there was no telling whether Roosevelt was referring to Odell’s bluff or his own: There had been no guarantee that he could override Platt’s control of the Senate to get his candidate confirmed. Nevertheless, after that conflict Roosevelt coined what was probably the best known of his many aphorisms. He wrote to a former Assembly colleague: “I have always been fond of the West African proverb, ‘Speak softly and carry a big stick; you will go far.’”

In the summer of 1899, Roosevelt had been governor for just half a year and was already considering his next political destination: the White House. As he prepared a trip to Texas for a Rough Rider reunion, he asked William Allen White to join him for a portion of the train ride to discuss his presidential prospects.

White, who had rocketed to national prominence on the strength of an 1896 editorial deriding the anti-business policies of William Jennings Bryan in the Emporia, Kansas, Emporia Gazette, first met Roosevelt on a visit to Washington the next year. The editor, a laissez-faire conservative, was impressed by both “the splendor” of Roosevelt’s personality and his ideas – especially his growing revulsion at corporate abuses and his empathy for the working poor and their need for social and economic justice. Roosevelt was only a few steps ahead of White in this conversion, but White said his new friend “sounded in my heart the first trumpet call of the new time that was to be.” (He also made his point in a more plainspoken manner: “Roosevelt bit me, and I went mad.”)

White believed that if McKinley ran for a second term in 1900, Roosevelt would be in a strong position to win the GOP nomination in the 1904 election, and he was working to make that happen. On the trip to Texas, he organized campaign-style rallies to greet Roosevelt at every stop in Kansas and turned out larger crowds than McKinley had drawn in his 1896 campaign against Bryan. Prudently, Roosevelt wired the president to tell him how much sentiment he was finding for a second McKinley term and assured the press that he was not a candidate for president. But he also took White’s advice and sent personal notes to every editor and publisher he met who commented favorably on his chances in 1904.

White and Roosevelt had developed similar views on the excessive, monopolistic power of large corporate entities, or trusts. Roosevelt’s battle for the franchise tax made him aware of what he called the “growth of popular unrest and popular distrust” of large companies. He was finding that many voters who had backed McKinley in 1896 now thought the populist Bryan was, as the governor put it, “the only man who can control the trusts; and that the trusts are crushing the life out of small men.” Roosevelt drafted a proposal for regulating trusts as part of his second annual message to the New York legislature. After his friend Elihu Root, a corporate lawyer who had become McKinley’s secretary of war, toned down the text of the speech, the governor told his lawmakers that it was essential to not to punish the wealthy, but to curb abuses “of a very grave character” that it would be “worse than idle to deny.”

Once again, Roosevelt was set for conflict with Boss Platt, and the fight intensified when the governor backed a bill compelling companies to disclose information on “their structure and finance.” But this fight was one Roosevelt was destined to lose. While farmers and hourly workers were fully and personally aware of the dangers of the trusts, middle-class Americans had not realized the extent of the problem. The public never rallied around Roosevelt’s bill, and Platt and his cronies easily blocked it.

Nonetheless, Roosevelt was winning far too many battles for Platt’s comfort. And as his term was nearing its end in 1900, the governor showed every sign of wanting another. Platt devised a plan to get Roosevelt out of Albany: Engineer the governor’s nomination for vice president with McKinley as he ran for a second term. McKinley’s first-term vice president, Garret Hobart, had died of heart disease in November 1899. The 1900 convention, set for June in Philadelphia, could easily be charged to hail the hero of San Juan Hill. Roosevelt would be a reliable asset in the campaign, election would ensue, and he would be stifled and impotent for four years in the political graveyard of the vice presidency.

Roosevelt, who had already been named a New York delegate, was disconcerted as word of this maneuver spread. From Washington, Henry Cabot Lodge urged him to accept the nomination, arguing that it would be a stepping stone to the presidency in 1904. Others, however, doubted this strategy, and Roosevelt foresaw death from boredom with nothing to do but preside over the Senate. “As governor I can achieve something,” he said, “but as vice president, I should achieve nothing.” In any case, he couldn’t afford the $2,000 reduction in salary.

Roosevelt maintained he didn’t want the job, but bridled if anyone agreed that he shouldn’t have it; he issued an unequivocal denial of interest, only to equivocate the next day. Despite his advisors’ repeated warnings that he would be nominated if he appeared at the convention, he didn’t change his plans, and once there, he showed considerable pleasure at the adulation he received. One man stood in the way of the nomination: Mark Hanna, Republican Party chairman and McKinley’s primary political advisor, was opposed to Roosevelt. But McKinley didn’t take the stand, and the convention careened out of control. Hanna found himself shouting at the wallpaper. “Don’t any of you realize,” he erupted, “that there’s only one life between this madman and the presidency?” No one listened. McKinley and Roosevelt were running mates.

Roosevelt campaigned tirelessly, traveling 21,209 miles and delivering 673 speeches in 567 towns and cities in twenty-four states, speaking to a total of 3 million people. On Election Day, the McKinley-Roosevelt ticket won by 750,000 popular votes and a near two-to-one margin in the Electoral College. Among those traveling to Washington for the inauguration on March 4, 1901: Tom Platt and New York’s new governor, Benjamin Odell. “We’re off to Washington,” grinned Platt, “to see Teddy take the veil.”

Platt’s gloating was prescient: The vice presidency provided all the excitement of a convent. Roosevelt found it all he had expected - and less. While McKinley was “perfectly cordial,” he wrote, “he does not intend that I shall have any influence of any kind, sort or description in the administration from the top to the bottom.” He presided over the Senate for four days, until it adjourned for some eight months on March 8. With the Senate in recess, Roosevelt joined Edith and the children at Sagamore Hill for a family interlude in the spring, after which he took two trips west. He contemplated finishing his long-stalled legal degree and agreed to make a series of speeches in Vermont. But he told William Howard Taft, now governor-general of the Philippines, a job Roosevelt envied, that he had “ugly feelings” that he was “leading a life of unwarrantable idleness.” He was pessimistic about his prospects of winning the presidency; his own state would be against him at the convention in 1904, he said, and “my present position is one in which I can do absolutely nothing to shape policies. . . . It would be simply foolish for me to think seriously of my chances of getting the office.” At forty-two, he foresaw with “absolute horror” the fate of “the politician whose day has passed . . . and who haunts the fields of his former activity as a pale shadow of what he once was.”

On September 6, 1901, a young anarchist named Leon Czolgosz entered a receiving line to meet President McKinley at the Pan-American Exposition in Buffalo. When he got to the head of the line, he pulled out a revolver and shot the president twice in the abdomen. Eight days later, McKinley died of complications from his wounds. Theodore Roosevelt was President of the United States.