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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 1791 to 1792, during the presidency of George Washington. When he discovered the affair, Reynolds' husband, James Reynolds, subsequently blackmailed Hamilton over the affair, who paid him over $1,300, about a third of his annual income, to maintain the secrecy. In 1797, 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." Background In the summer of 1791, 23-year-old Maria Reynolds allegedly approached the married 34-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. He later recounted, "I took the bill out of my pocket and gave it to her. Some conversation ensued from which it was quickly apparent that other than pecuniary consolation would be acceptable." The two began an illicit affair that would last, with varying frequency, until approximately June 1792. Over the course of those months, while the affair took place, James Reynolds was well aware of his wife's unfaithfulness. He continually supported their relationship to gain regular blackmail money from Hamilton. In the Reynolds Pamphlet, Hamilton goes as far as to argue that James Reynolds, along with his wife, had conspired the scheme to "extort money from me." The common practice in the day was for the wronged husband to seek retribution in a pistol duel, but Reynolds, realizing how much Hamilton had to lose if the activity came into public view, insisted on monetary compensation instead. After Hamilton had shown unequivocal signs that he wanted to end the affair in autumn 1791, Hamilton received two letters on December 15, 1791, one each from Mrs. and Mr. Reynolds. The first letter, from Maria, warned of her husband's knowledge and of James' attempting to blackmail Hamilton. By then, Hamilton discontinued the affair and briefly ceased to visit, but both James and Maria were apparently involved in the blackmailing scheme, as both sent letters inviting Hamilton to continue his visits. After extorting $1000 in exchange for secrecy over Hamilton's adultery, James Reynolds rethought his request for Hamilton to cease his relationship with Maria and wrote inviting him to renew his visits "as a friend," only to extort forced "loans" after each visit, which the most-likely-colluding Maria solicited with her letters. By May 2, 1792, James changed his mind again and requested for Hamilton to stop seeing his wife but not before James had received additional payment. In the end, the blackmail payments totaled over $1,300 including the initial extortion (equivalent to $31,000 in 2023). Hamilton had possibly become aware of both Reynoldses being involved in the blackmail and both welcomed and strictly complied with James' request to end the affair. The cultural historian Tilar J. Mazzeo has advanced a theory that the affair never happened. Outside of the Reynolds Pamphlet, there is no evidence that the affair actually occurred. Others connected with the scandal, from James Monroe, who held the papers relating to James Reynolds, to Maria Reynolds herself, said that it was a coverup for a financial scandal. Hamilton never produced the manuscript copies of Maria's letters, but both the newspapers and Maria suggested obtaining a handwriting sample. Hamilton said that they had been placed with a friend, who claimed that he had never seen them, which suggests that the letters may have been forged. The newspaper writers also pointed out that Maria's letters correctly spell long, complex words but sometimes misspelled simple words in a way that made no phonetic sense. As the Thomas Jefferson biographer Julian P. Boyd stated, the letters could resemble what an educated man believed an uneducated woman's love letters to look like. A Hamilton biographer also stated that the letters look like the letters between Alexander and his wife, Eliza, which could explain why Eliza burned her letters. Scandal In November 1792, after James Reynolds was jailed for participation in a scheme involving unpaid back wages intended for Revolutionary War veterans, he used his own knowledge about Hamilton's sex affair to bargain his way out of his own troubles. Reynolds knew that Hamilton would have to choose between revealing his affair with Maria or falsely admitting complicity to the charges. James Monroe, Abraham Venable, and Frederick Muhlenberg were the first men to hear of this possible corruption within the nation's new government, and on December 15, 1792, they decided to confront Hamilton personally with the information that they had received, supported by the notes of Hamilton's payments to Reynolds that Maria had given them to corroborate her husband's accusations. Denying any financial impropriety, Hamilton revealed the true nature of his relationship with the Reynoldses in all of its unsavory details. He turned over the letters from both of them. Apparently convinced that Hamilton was not guilty of the charge of public misconduct, Monroe, Venable, and Muhlenberg agreed not to make public the information and documents on the Reynolds Affair. Monroe and his colleagues assured Hamilton that the matter was settled. However, Monroe sent the letters to his close personal friend, Thomas Jefferson. Jefferson and Hamilton were self-described nemeses, and five years after receiving the letters, Jefferson used the knowledge to start rumors about Hamilton's private life. Also in 1797, when Hamilton no longer held the post of Secretary of the Treasury, the details of his relationship with Maria and James Reynolds came to light in a series of pamphlets authored by the journalist James Thomson Callender. Included were copies of the documents that Hamilton had furnished to the Monroe commission in December 1792. Hamilton confronted Monroe over the leakage of the supposedly-confidential documents. Monroe denied any responsibility. Hamilton came very close to calling Monroe a liar, and Monroe retorted that Hamilton was a scoundrel and challenged him to a duel. The duel was averted by the intercession of Aaron Burr. After writing a first draft in July 1797, on August 25, Hamilton responded to Callender's revelations by printing his own 95-page pamphlet, Observations on Certain Documents, lat.... Discover the Stephanie Dray popular books. Find the top 100 most popular Stephanie Dray books.