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When General David Petraeus resigned as director of the CIA in November 2012, after his affair with his hagiographer, Paula Broadwell, came to the attention of the FBI, he offered no excuses for having fallen in lust with a much younger woman. “I showed extremely poor judgment by engaging in an extramarital affair,” Petraeus wrote. “Such behavior is unacceptable, both as a husband and as the leader of [the CIA].”

The unexpected downfall of America’s most prominent recent soldier-hero was a variation on one of the oldest stories in the world. The inevitable parallel was biblical—King David smitten with Bathsheba, the wife of one of his officers. But there was also precedent in America’s founding sex scandal, the Reynolds affair, which saw Alexander Hamilton, husband, father and the country’s first treasury secretary, entangled with Maria Reynolds, the wife of a small-time crook. Both affairs raised the specter of blackmail, and both exposed a flawed alpha male to the jeers of the public. Then as now, other leaders had to decide whether to pile on or look past the tarnish to a hero’s better nature.

Alexander Hamilton was a self-made success story, a Caribbean immigrant who impressed George Washington enough to be tapped for his wartime staff, then tapped again to run the Treasury Department in 1789. Along the way he married Elizabeth Schuyler, a lovely heiress. The young hotshot seemed to have made a happier family than the one he grew up in—Hamilton’s parents back in the islands never married, and his father had simply walked out when Alexander was a boy.

In the summer of 1791 a woman called on Hamilton at his Treasury Department office in Philadelphia. Maria Reynolds claimed that she had just been deserted by a cruel husband. She said she had heard the secretary was a generous man and wondered if he could help her return to her family in New York State. Hamilton offered to come to her room that night with a loan. When he arrived, Hamilton wrote later, he found that “other than pecuniary consolation would be acceptable.”

All the obvious preconditions for an affair were in place. Hamilton was 34 and charming. Maria was 23 and attractive. Elizabeth Hamilton was out of town, having fled the Philadelphia summer to be with her parents in Albany. Maria’s sob story had an extra allure for Hamilton, the son of an abandoned mother.

Their affair was soon complicated by the reappearance of James Reynolds, the allegedly cruel husband, who tried to befriend Hamilton himself, asking for a Treasury Department job. Hamilton strung James along, hoping to stay on good terms with both his lover and her mate. When Elizabeth Hamilton returned to town, he had to keep the affair secret from her as well.

In December 1791 the affair turned disastrous. Hamilton got an angry letter from James, who claimed to have just discovered what was going on, and a weepy one from Maria, bewailing her exposure. There was of course no discovery and no exposure: The Reynoldses had been in cahoots all along, baiting a honey trap for their famous friend. Hamilton, whose annual salary was $3,000, now had to pay James Reynolds $1,000 for his silence.

Hamilton broke free of his blackmailers in the spring of 1792. James, looking for his next score, tried to cash the back-pay certificate of a dead veteran who, inconveniently, turned out to be still alive. While in jail for that scam, Reynolds hinted at a juicier one, claiming that he and the treasury secretary had engaged in insider trading—Hamilton supplying advance notice of policy decisions, Reynolds making the appropriate investments. In December three congressman appeared in Hamilton’s office threatening to take Reynolds’ story to President Washington, unless Hamilton explained himself. At home that night, he showed them the love letters and the blackmail notes and revealed his true connection to the Reynoldses. Satisfied that there was no public corruption involved, the congressmen assured Hamilton they would let the matter drop, though one of them, James Monroe, made a copy of all the letters.

So the matter rested—until 1797. Hamilton had left the Treasury but remained a leader of the Federalist Party, trading blows with Thomas Jefferson’s Republicans. In the summer, Republican journalist James Callender attacked Hamilton in a pamphlet. Callender knew about the affair with Maria but insisted that Hamilton’s real business with the Reynoldses was insider trading with James. Callender’s ultimate source was Monroe, who had shared everything he knew with other Republicans, including Jefferson. Hamilton now decided he had to tell the whole world the whole truth. “The charge against me,” he wrote in a pamphlet of his own, “is a connection with one James Reynolds for purposes of improper pecuniary speculation. My real crime is an amorous connection with his wife.” He replayed the affair over 95 pages, quoting all the evidence he had given his congressional accusers five years earlier.

We expect officeholders to avoid affairs, lest they bend the rules or break the law to hide their secret sins. The Reynolds affair reversed this scenario. James Reynolds shook Hamilton down, for money; years later, Hamilton exposed his own adultery to show that he had not committed insider trading. He revealed his secret sins to prove that he had not violated the public trust.

Hamilton, like Petraeus, was a great man brought low by pride. Hamilton restored America’s finances; Petraeus brought Iraq back from the brink of disaster in 2007 by masterminding a military surge. Both men thought they could wield their power over the human heart: Hamilton saving a woman in distress, Petraeus bedding an admiring biographer. The reward, in both cases, was a carnival of catcalls. Petraeus became the butt of TV comics and tabloid headlines. Hamilton experienced the 18th-century equivalent as Republican newspapers snarked about the Reynolds affair for the rest of his life.

Most interesting was the reaction of Hamilton’s peers. Monroe and Jefferson practiced the politics of personal destruction, hoarding dirt about Hamilton and releasing it years later, like a time bomb. Other politicians dismissed the Reynolds affair with worldly shrugs. If Hamilton “fornicates with every female in the cities of New York and Philadelphia,” wrote one Federalist judge, “he will rise again, for purity of character… is not necessary for public patronage.”

Hamilton’s greatest patron, George Washington, took the longest view. In the summer of 1797, when the Reynolds affair was blowing at gale force, the former president sent his former aide a silver-plated wine cooler—“a token of my sincere regard and friendship for you,” Washington wrote in the accompanying note. “I pray you to present my best wishes, in which Mrs. Washington joins me, to Mrs. Hamilton and the family.” In other words: I still think well of you, despite the stupid thing you have done; my wife and I hope you and your wife still think well of each other. The note was a masterpiece of proportion and tact.

Who has shown a similar sense of proportion in the Petraeus affair? Petraeus’ offense was arguably worse than Hamilton’s since the information that might be wrung from the director of the CIA could be more sensitive than anything possessed by a treasury secretary. But once Petraeus admitted his affair to President Barack Obama (and to Mrs. Petraeus) was he still at risk? “Clearly this is not someone who is going to be subject to blackmail,” said Senator Roy Blunt of Missouri.

George Washington turned to Hamilton one more time, tapping him to be second in command of the U.S. Army in case the French invaded in 1798. Elizabeth Hamilton stuck by her man until his death in an 1804 duel with Aaron Burr, and for 50 years of widowhood. We will have to see what lies ahead for David Petraeus.


Originally published in the April 2013 issue of American History. To subscribe, click here.