Hamilton–Reynolds affair

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 would never serve 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.