Hamilton–Reynolds affair

The Hamilton–Reynolds affair was the first major sex scandal in United States political history. It involved Secretary of the Treasury Alexander Hamilton, who conducted an affair with Maria Reynolds from 1791 to 1792, during the presidency of George Washington. After he discovered the affair, Reynolds' husband, James Reynolds, blackmailed Hamilton, who paid him over $1,300 in hush money, about a third of his annual income. In 1797, Hamilton publicly admitted to the affair after his political enemies accused him of financial corruption during his time as the Treasury Secretary. Hamilton responded by writing, "The charge against me is a connection with one James Reynolds for purposes of improper pecuniary speculation. My real crime is an amorous connection with his wife, for a considerable time with his privity and connivance."

James Monroe was among the first men to be informed of this scandal, and he leaked information about it to Thomas Jefferson. Jefferson used the information to start rumors about Hamilton's private life. In 1797, Hamilton and Monroe challenged each other to a duel over this incident. The duel was averted by the intercession of Aaron Burr.