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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 to , during the presidency of George Washington. In , Hamilton publicly admitted to the affair after his political enemies attacked and 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 , Hamilton and Monroe challenged each other to a duel over this incident. The duel was averted by the intercession of Aaron Burr. In the summer of , year-old Maria Reynolds allegedly approached the married year-old Alexander Hamilton in Philadelphia to request his help and financial aid by claiming that her husband, James, had abandoned her.

Hamilton did not have any money on him, so he retrieved her address to deliver the funds in person. Once Hamilton arrived at the boarding house at which Maria was lodging, she brought him upstairs and led him into her bedroom.