Hamilton stepped out of the limelight when he resigned his cabinet post in 1795, but he remained in the game, acting as an unofficial advisor to Washington and drafting his Farewell Address (To George Washington, July 30, 1796). Eager to maintain his influence on national policy under Washington’s successor, Hamilton advised President John Adams’s cabinet behind the new President’s back—until Adams found out. The resulting clash helped to split the Federalists into two warring factions and severely damaged Hamilton’s political career.
The beginning of Hamilton’s end was the presidential election of 1800. Hoping to elect Federalist Charles Cotesworth Pinckney as President over Adams, Hamilton savaged the incumbent Adams in a pamphlet. Attacking Adams’s character as well as his politics, Hamilton went too far once too often, leading many of his Federalist friends and followers to conclude that he lacked discretion and was thus an unfit leader.
Hamilton’s national political career was foundering, but he didn’t surrender quietly. When the election produced a tie between Republicans Burr and Jefferson—a Hamiltonian nightmare come true—he campaigned against Burr behind the scenes, though his efforts had little impact. His letters to Gouverneur Morris (December 26, 1800), John Rutledge Jr. (January 4, 1801), and James A. Bayard (January 16, 1801) show his profound distrust of his quondam friend and foe. Looking back on Jefferson’s victory in 1802, Hamilton tried to adapt Republican electoral strategies to aid the Federalists. In the same way that fervor for the French Revolution had fueled the Republicans, he reasoned, devotion to the Christian religion could fuel the Federalists (To James A. Bayard, April 1802).
Hamilton’s private life was also tumultuous during this period. His thriving law practice enabled him to build “The Grange,” a country home for his family in upper Manhattan, the only home that Hamilton—otherwise a lifelong renter—ever owned. But for the most part, Hamilton’s final years were a tangle of scandals and tragedies, as his flaws and excesses played themselves out. In 1796, when Republicans hinted that Hamilton had misused Treasury funds, he defended himself in what came to be known as the “Reynolds Pamphlet,” asserting that what looked like peculation was in fact a series of blackmail payments made to hush up his adulterous affair with Maria Reynolds in 1791–1792. Five years later, in 1801, Hamilton’s oldest son Philip died after fighting a duel defending his father’s name (To Benjamin Rush, March 29, 1802). Hamilton never fully recovered.
Not surprisingly, his letters in this period are dark and moody, a far cry from the fiery salvoes of his younger days. His “Memorandum on the Design for a Seal of the United States” (c. May 1796) shows the depth of his fears about the fate of the nation. Depicting a French Revolutionary “Colossus” with one foot on the European continent and the other hovering over North America, it is political panic put to paper. Hamilton wasn’t alone in his fears; the late 1790s was a period of intense partisanship and dire predictions. But true to character, he responded by breaking rules and crossing lines—or at least, he tried. Theodore Sedgwick didn’t listen when Hamilton suggested (February 2, 1799) raising and then marching an army on the Republican stronghold of Virginia to quash its resistance to the Alien and Sedition Acts. One year later, New York Governor John Jay likewise ignored Hamilton’s plea (May 7, 1800) to change the rules for choosing presidential electors in the middle of the election.
These troubled years also drew from Hamilton a series of unusually reflective letters, as he wrestled with the fall of the Federalists and the unraveling of his political career. When enemies snickered about his low origins, Hamilton defended himself by describing his early years in a letter to his friend William Jackson (August 26, 1800), his only extended discussion of his illegitimacy on paper.
Aware that he was swimming against the nation’s democratic tide, Hamilton half-jokingly began to call himself a “disappointed politician,” as he did in his letter to Charles Cotesworth Pinckney (December 29, 1802). That same year, he confessed a sad truth in a letter (February 29, 1802) to his friend Gouverneur Morris: “this American world was not made for me.”