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==Reynolds affair== {{main|Hamilton–Reynolds affair}} [[File:James Monroe (1758-1831).jpg|thumb|[[James Monroe]], a Democratic-Republican congressman and Hamilton's political rival]] In summer 1797, Hamilton became the first major American politician publicly involved in a sex scandal.<ref name=Brookhiser3>{{cite book |first=Richard |last=Brookhiser |title=Alexander Hamilton, American |url=https://books.google.com/books?id=KNqw3yCfG5YC&pg=PA3 |year=2011 |page=3 |publisher=Simon and Schuster |isbn=978-1-4391-3545-7}}</ref> Six years earlier, in summer 1791, 34-year-old Hamilton became involved in an affair with 23-year-old [[Maria Reynolds]]. According to Hamilton, Maria approached him at his house in [[Philadelphia]], claiming that her husband James Reynolds was abusive and had abandoned her, and she wished to return to her relatives in New York but lacked the means.<ref name=schachner />{{rp|366–369}} Hamilton recorded her address and subsequently delivered $30 personally to her boarding house, where she led him into her bedroom and "Some conversation ensued from which it was quickly apparent that other than pecuniary consolation would be acceptable". The two began an intermittent illicit affair that lasted approximately until June 1792.<ref name="Reynolds Pamphlet">{{cite web |last1=Hamilton |first1=Alexander |title=Printed Version of the "Reynolds Pamphlet", 1797 |url=https://founders.archives.gov/documents/Hamilton/01-21-02-0138-0002 |website=Founders Online |publisher=National Archives |access-date=July 17, 2016 |archive-date=July 10, 2016 |archive-url=https://web.archive.org/web/20160710111423/http://founders.archives.gov/documents/Hamilton/01-21-02-0138-0002 |url-status=live}}</ref> James Reynolds was aware of his wife's infidelity, and likely orchestrated it from the beginning. He continually supported their relationship to extort blackmail money regularly from Hamilton. The common practice of the day for men of equal social standing was for the wronged husband to seek retribution in a duel. But Reynolds, of a lower social status and realizing how much Hamilton had to lose if his activity was made public, resorted to extortion.<ref>{{harvnb |Freeman |2001}}</ref> After an initial request of $1,000,<ref>{{cite web |last1=Reynolds |first1=James |title=Letter from James Reynolds to Alexander Hamilton, 19 December 1791 |url=https://founders.archives.gov/documents/Hamilton/01-10-02-0045 |website=Founders Online |publisher=National Archives |access-date=December 24, 2019 |archive-date=July 25, 2020 |archive-url=https://web.archive.org/web/20200725021529/https://founders.archives.gov/documents/Hamilton/01-10-02-0045 |url-status=live}}</ref> with which Hamilton complied, Reynolds invited Hamilton to renew his visits to his wife "as a friend"<ref>{{cite web |last1=Reynolds |first1=James |title=Letter from James Reynolds to Alexander Hamilton, 17 January 1792 |url=https://founders.archives.gov/documents/Hamilton/01-10-02-0106 |website=Founders Online |publisher=National Archives |access-date=December 24, 2019 |archive-date=August 7, 2020 |archive-url=https://web.archive.org/web/20200807020238/https://founders.archives.gov/documents/Hamilton/01-10-02-0106 |url-status=live}}</ref> only to extort forced "loans" after each visit that, most likely in collusion, Maria solicited with her letters. In the end, the blackmail payments totaled over $1,300 including the initial extortion.<ref name=schachner />{{rp|369}} Hamilton at this point may have been aware of both spouses being involved in the blackmail,<ref>Murray, p. 165.</ref> and he welcomed and strictly complied with James Reynolds' eventual request to end the affair.<ref name="Reynolds Pamphlet"/><ref>{{cite web |last1=Reynolds |first1=James |title=Letter from James Reynolds to Alexander Hamilton, 2 May 1792 |url=https://founders.archives.gov/documents/Hamilton/01-11-02-0284 |website=Founders Online |publisher=National Archives |access-date=December 24, 2019 |archive-date=July 25, 2020 |archive-url=https://web.archive.org/web/20200725020135/https://founders.archives.gov/documents/Hamilton/01-11-02-0284 |url-status=live}}</ref> In November 1792, James Reynolds and his associate Jacob Clingman were arrested for counterfeiting and [[speculating]] in Revolutionary War veterans' unpaid back wages. Clingman was released on bail and relayed information to Democratic-Republican congressman [[James Monroe]] that Reynolds had evidence incriminating Hamilton in illicit activity as Treasury Secretary. Monroe consulted with congressmen Muhlenberg and Venable on what actions to take and the congressmen confronted Hamilton on December 15, 1792.<ref name="Reynolds Pamphlet"/> Hamilton refuted the suspicions of [[financial speculation]] by exposing his affair with Maria and producing as evidence the letters by both of the Reynolds, proving that his payments to James Reynolds related to blackmail over his adultery, and not to treasury misconduct. The trio agreed on their honor to keep the documents privately with the utmost confidence.<ref name=schachner />{{rp|366–369}} Five years later however, in the summer of 1797, the "notoriously scurrilous" journalist [[James T. Callender]] published ''A History of the United States for the Year 1796''.<ref name=McDonald />{{rp|334}} The pamphlet contained accusations based on documents from the confrontation of December 15, 1792, taken out of context, that James Reynolds had been an agent of Hamilton. On July 5, 1797, Hamilton wrote to Monroe,<ref>{{Cite web|title=From Alexander Hamilton to James Monroe|url=https://founders.archives.gov/documents/Hamilton/01-21-02-0078-0001|date=July 5, 1797|access-date=April 28, 2025|via=[[Founders Online]]}}</ref> Muhlenberg,<ref>{{Cite web|title=From Alexander Hamilton to Frederick A. C. Muhlenberg|url=https://founders.archives.gov/documents/Hamilton/01-21-02-0079|date=July 5, 1797|access-date=April 28, 2025|via=[[Founders Online]]}}</ref> and Venable,<ref>{{Cite web|title=From Alexander Hamilton to Abraham B. Venable|url=https://founders.archives.gov/documents/Hamilton/01-21-02-0081|date=July 5, 1797|access-date=April 28, 2025|via=[[Founders Online]]}}</ref> asking them to confirm that there was nothing that would damage the perception of his integrity while Secretary of Treasury. All but Monroe complied with Hamilton's request. This led to Hamilton and Monroe engaging in an argument that almost culminated in a duel, before the conflict was averted by Aaron Burr.<ref>{{Cite web|title=That Time Alexander Hamilton Almost Dueled James Monroe|url=https://www.smithsonianmag.com/history/time-when-alexander-hamilton-almost-dueled-james-monroe-180957045/|date=October 26, 2015|access-date=May 6, 2025|via=[[Smithsonian Magazine]]}}</ref><ref>{{Cite web|last1=Stello|first1=Heidi|title=The Near Duel Between James Monroe and Alexander Hamilton|url=https://academics.umw.edu/jamesmonroepapers/2015/09/03/the-near-duel-between-james-monroe-and-alexander-hamilton|date=September 3, 2015|access-date=May 6, 2025|via=[[University of Mary Washington]]}}</ref> Hamilton then published a 100-page booklet, later usually referred to as the ''[[Reynolds Pamphlet]]'', and discussed the affair in indelicate detail for the time. Hamilton's wife Elizabeth eventually forgave him, but never forgave Monroe.<ref>{{cite AV media |title=Alexander Hamilton |medium=Audiobook |people=Chernow |date=December 26, 2004 |time=12:58 |chapter=Epilogue}}</ref> Although Hamilton faced ridicule from the Democratic-Republican faction, he maintained his availability for public service.<ref name=McDonald />{{rp|334–336}}
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