As the first secretary of the U.S. Treasury, Alexander Hamilton built the foundations of the national banking system and wielded more power in the earliest years of American democracy than any other man beside George Washington. Yet unlike Washington, and unlike his longtime nemesis Thomas Jefferson, Hamilton never served as U.S. president—not only because he died in a duel by the hands of Aaron Burr.

In fact, as any fan of Lin-Manuel Miranda’s blockbuster hip-hop musical Hamilton knows, Hamilton torpedoed his own presidential ambitions for good in 1797, when he published a tell-all pamphlet about the sordid details of his earlier affair with a married woman, Maria Reynolds, and the blackmail payments he made to her husband to cover up the affair.

Complete with illicit meetings, payments of “hush money” and allegations of corruption, the Reynolds Affair had all the trappings of a modern-day political sex scandal, and was all the more shocking for being the first such drama in U.S. history.

According to Hamilton’s version of events, which he shared with the world in 1797, Maria (probably pronounced “Mah-rye-ah”) Reynolds came to his family home in Philadelphia in the summer of 1791, and asked to speak to him in private. The 23-year-old blonde presented herself as a damsel in distress, telling the treasury secretary that her abusive husband, James Reynolds, had left her and their young daughter to run off with another woman. Maria said she was destitute, and asked for money to help her get to friends in New York.

At the time, Hamilton was at the height of his influence as treasury secretary, and could be considered the second most powerful man in the United States. His outspoken style earned him many enemies, which as biographer Ron Chernow has written “should have made him especially watchful of his reputation.”

And yet that night, Hamilton took a 30-note bill to the rooming house where Maria Reynolds was staying. She led him upstairs, where, in his words, “it was quickly apparent that other than pecuniary consolation would be acceptable.” They began a sexual relationship, meeting often at Hamilton’s own home after his devoted wife, Eliza, took their children to visit her father in Albany.

Soon enough, Maria’s husband, James Reynolds, confronted Hamilton via letter and demanded $1,000 (the equivalent of nearly $25,000 today) to keep quiet about the affair. Hamilton paid the full amount in two installments by January 1792, but Reynolds stayed in Philadelphia despite his promise to leave town. He even encouraged Hamilton to resume the affair with his wife, who claimed to be devoted to her powerful lover.

That spring, Reynolds repeatedly asked Hamilton for smaller amounts in “loans,” until finally Hamilton stopped seeing Maria for good in the summer of 1792.

In November, James Reynolds and an associate, Jacob Clingman, were arrested and imprisoned for their involvement in a scheme to defraud the government by posing as the executors of deceased Revolutionary War veterans to get their back pay. While out on bail, Clingman approached his former employer Frederick Muhlenberg, a congressman from Pennsylvania, and claimed that Reynolds had been involved in illegal speculation with none other than Alexander Hamilton. With two colleagues from Virginia, James Monroe and Abraham Venable, Muhlenberg visited James Reynolds in jail and Maria Reynolds at her home, then went to Hamilton’s to confront him in person about these suspected illegal dealings.

To their surprise and embarrassment, Hamilton came clean about his extramarital affair, even sharing the letters he received from both Mr. and Mrs. Reynolds. Monroe, Muhlenberg and Venable left convinced that Hamilton was innocent of all except adultery, and supposedly promised not to say anything more to anyone. But unbeknownst to Hamilton, Monroe sent copies of the documents Hamilton had shown them to Jefferson, while John Beckley, then the clerk for the House of Representatives, also kept a copy.

Over the next several years, Hamilton retired from his Cabinet post and went back to New York to his law practice. Maria and James Reynolds split up (with Aaron Burr serving as Maria’s attorney) and Maria married Clingman the same day her divorce became official.

Then in the fall of 1796, in a series of essays written under the name “Phocion,” Hamilton threw shade on Jefferson’s private life, including a pretty big hint about his rumored relationship with one of his slaves, Sally Hemings. In response, the scandal-mongering journalist James Callender struck back hard, writing in the summer of 1797 that not only that Hamilton had his own sexual indiscretions, but that Hamilton had used federal funds to illegally speculate in government securities with Reynolds.

Though John Buckley likely gave Callender access to the documents after Federalists fired him as House clerk, Hamilton himself would blame Monroe. The two men nearly got into a duel over it, before (in another supreme irony) Burr interceded to talk them down. For her part, Eliza Hamilton would reportedly carry a grudge against Monroe for years to come.

Given the charges against him, Hamilton decided his best option was to come clean about his infidelity so he could defend himself on the speculation charges, which would not only ruin his career but permanently stain the Federalist Party and the U.S. Treasury. To that end, in late August 1797 he published what became known as the Reynolds Pamphlet, in which he shared the details of his affair with Maria and the subsequent blackmail payments he made to James Reynolds, including excerpts from their letters.

While the Reynolds Pamphlet successfully refuted the more serious accusations against Hamilton, the sordid revelations of his affair humiliated his wife and permanently ended any hope he might have had of becoming president of the United States. It didn’t destroy his career, however.

He continued to exert influence during President John Adams’ Federalist administration, until his feud with Adams exploded into a public attack on the incumbent president just before the election of 1800. Adams lost to Jefferson that year, marking the beginning of the end for the Federalist Party.

VIDEO: Alexander Hamilton Alexander Hamilton’s support of Thomas Jefferson over Aaron Burr in the 1800 U.S. presidential election eventually led to his own demise. Find out more about the first Secretary of the Treasury in this video.