Some of the arguments urged by the Federalists sound very familiar today: “Federalist leaders pelted Hamilton with letters about the expediency of supporting Burr and ending Virginia’s political hegemony. Because Burr lusted after money and power, they thought they could strike a bargain with him. They worried less about Burr’s loose morals than about what they perceived as Jefferson’s atheism. . . . John Marshall and others thought Burr a safer choice than Jefferson, who might try to recast the Constitution to conform to his ‘Jacobin’ tenets. . . . Fisher Ames feared that Jefferson was ‘absurd enough to believe his own nonsense’ while Burr might at least ‘impart vigor to the country.’ ” Ah, vigor! Burr, these men were saying, could at least be a “winner,” and there was no shortage of energy there.
Hamilton and Jefferson had been the best of enemies ever since they met in 1789 in George Washington’s cabinet, and the Little Lion and the Sage of Monticello did not get along, inadvertently starting the two-party system, which none of the Founders had imagined would develop, and conducting it on a level of personal rancor that seems remarkable even today. By 1792 they were conducting battle through the newspapers. Journalist James Callender would expose both Jefferson’s affair and his children with his slave Sally Hemings as well as Hamilton’s affair with and blackmail by Maria Reynolds, which took place while he was still in the government, in Philadelphia, in 1796.
Praising Jefferson did not come easily to Hamilton, as was evident in his opening words to James Bayard, the Delaware congressman he was lobbying on Jefferson’s behalf: “I admit that his politics are tinctured with fanaticism, that he is too much in earnest in his democracy; that he has been a mischievous enemy to the principal measures of our past administration, that he is crafty and persevering in his objects, that he is not scrupulous about the means of success, nor very mindful of truth, and that he is a contemptible hypocrite,” he began in what is undoubtedly the strangest opening to an endorsement ever made in political history.
But Hamilton went on to say that with all his faults Jefferson was a rational man with coherent ideas who operated within the normative range of accepted behavior in life and in politics, while Burr was something fundamentally different— a man for whom norms, rules, and boundaries didn’t exist. In 1792, Hamilton had taken his measure of Burr and never moved from it: Burr was “unprincipled both as a public and private man . . . for or against nothing but as it suits his interest or ambition . . . determined . . . to make his way to be the head of the popular party . . . and to climb . . . to the highest honors of the state.” Now Hamilton warned friends about Burr’s debts and the scandals involving his business investments, calling him a profligate, a voluptuary, unprincipled, and dangerous.
Embracing Burr, Hamilton said, would sign the Federalists’ “death warrant,” and he warned of the impact abroad: “No agreement with him could be relied on,” he wrote to Theodore Sedgwick. “The appointment of Burr as president would disgrace our country abroad.” Above all, he stressed the shame to the party if it involved itself with a man of Burr’s character and said, according to Chernow, that “if they installed Burr as president” he “would withdraw from the party, or even from public life.”