“My real crime is an amorous connection with his wife…” (Hamilton 1797) and with that Alexander Hamilton ended his political career. He had been accused of financial crimes, admitted to adultery, and fallen victim to a changing public opinion of morality.

                But what if Hamilton’s downfall was not due to his own hubris but the machinations of others? I first came across this theory in an article by Caroline V. Hamilton in an article called “The Erotic Charisma of Alexander Hamilton”. She speculates, based on an earlier biography of Hamilton by Robert Hendrickson, that the affair was the result of a collusion between leading Republican operators. (C. V. Hamilton 2011) Political conspiracy, color me intrigued.

                The whole theory is centered on a letter written to Hamilton by his friend Robert Troup on June 15, 1791. Troup warns Hamilton

“There was every appearance of a passionate courtship between the Chancellor [Robert R. Livingston], Burr, Jefferson & Madison when the two latter were in Town. Delenda est Carthago[1] I suppose it the Maxim adopted with respect to you. They had better be quiet, for if they succeed they will tumble the fabric of the government in ruins to the ground. Upon this subject however I cannot say that I have the smallest uneasiness. You are too well seated in the hearts of the citizens of the Northern & Middle States to be hunted down by them. That your foes may be confounded & that your administration may encrease in success & lustre is the cordial wish of.” (Troup 1791)

                This meeting did in fact happen during Jefferson and Madison’s tour of the north which was actually a cover for their building support for their new Republican party. They met with him while he was in residence in New York City rather than his country house, Clermont, where they would be less visible.

                Livingston was the perfect conspirator to join with Burr, Jefferson, and Madison. He had begun to turn his back on the Federalists when he was denied a job in Washington’s administration. Livingston also shared an animosity with Hamilton that dated back to the war. In fact, it was most likely Hamilton that kept Livingston out of office under Washington.

                Then there is James Reynolds. He was a small time crook. His go to crime was buying devalued government securities from Revolutionary War veterans, giving them a small amount of money and collecting a larger sum for themselves. He had been charged for this but escaped prosecution every time. Its possible he was known to Livingston or Burr in their legal capacities. He would have to pimp his wife for this conspiracy to work and she would have to agree to it. (Cogan 1996)

                Maria, James, and their daughter moved to Philadelphia from New York some time before the summer of 1791. Some time in June Maria showed up at Hamilton’s house to ask for money because her husband had mistreated her and left her and her daughter to fend for themselves. Interestingly she claimed to be a Livingston by marriage, the sister of Mr. G. Livingston. When he went to her house that evening to deliver the money she made it clear that “other than pecuniary consolation would be acceptable.” (A. Hamilton 1797)

                In December of 1791 Reynolds “found out” about the affair and began writing letters to Hamilton first writing “I am very sorry to find out that I have been so Cruelly treated by a person that I took to be my best friend instead of that my greatest Enimy. You have deprived me of every thing that’s near and dear to me..” (Reynolds 1791) Four days later he  wrote “This preposial to make to you. give me the Sum Of thousand dollars and I will leve the town and take my daughter with me and go where my Friends Shant here from me and leve her to Yourself to do so as you thin proper.[2] (Reynolds, James Reynolds to Alexander Hamilton, 19 December 1791 1791)

                Reynolds wrote a receipt “Received December 22 of Alexander Hamilton six hundred dollars on account of a sum of one thousand dollars due to me.” (Reynolds, James Reynolds to Alexander Hamilton, [22 December 1791] 1791) and on January 3 “Received Philadelphia January 3 179[2] of Alexander Hamilton four hundred dollars in full of all demands.” (Reynolds, James Reynolds to Alexander Hamilton, [3 January 1792] 1792) That should have been the blackmail, but blackmailers are seldom satisfied. On January 17 Reynolds wrote to Hamilton encouraging him to continue his visits to Maria, at their house. (Reynolds, James Reynolds to Alexander Hamilton, 17 January 1792 1792) Then came the requests for loans $30, $45, $30, $300, $50, $200. Reynolds was not shy.[3] Nor was he always successful as Hamilton did not fulfill his every request for money.

                Later in that year Reynolds and his partner, Jacob Clingman were arrested for trying to make a third man perjure himself in order to gain access to the estate of a deceased soldier. Reynolds hinted that he knew something about the Secretary of the Treasury that could shake his foundations. He claimed the Hamilton had given him federal money with which to speculate with. Congress launched an investigation led by Frederick Augustus Muhlenberg, Abraham Venable, and James Monroe.

                They interviewed Hamilton on December 15, 1792. He unabashedly admitted to the adultery and he showed them the receipts that proved he was being blackmailed by the Reynolds. They agreed that Hamilton had most likely was set up and he was not guilty of any financial crimes. Aside from a few rumors that got out nothing came from the affair. (Cogan 1996)

                There is one little thing that happens in 1793 that brings back the conspiracy. In 1793 Maria divorced Reynolds. Her lawyer was Aaron Burr. (C. V. Hamilton 2011)

                Years later, everyone had all but forgotten about Hamiliton’s affair when James Thomson Callender published two pamphlets in 1797 detailing the affair and financial crimes. Callender was a Scottish scandalmonger who had fled to the United States ahead of sedition charges. He immediately began again when he got to America, attacking Hamilton, then John Adams, who had him charged and imprisoned under the Alien and Sedition Acts. He finally attacked Jefferson, who had pardoned him when he became president. Callender was found in the James River in 1803, supposedly he had drowned while drunk. The Scottish Callender’s name may have shown some connection to Callendar, the home of the Livingston family in Scotland.

                It was to these pamphlets that Hamilton was responding with what became known as the Reynolds Pamphlet where he widely proclaimed that he was guilty of an affair and not fiscal impropriety. Proving to the public that he was not a virtuous man and unworthy of public office. (Cogan 1996)

                So here’s how I see it. Hamilton played no small roll in the in the end of civility in American politics. He made enemies of men like Jefferson, Madsion, and Burr all while enjoying Washington’s protection. Its not surprising that his enemies would try to induce him to commit crimes that would collapse his world on his own head. All the while Hamilton believed the conspiracy was only between a husband and wife bent on extorting money from him. (A. Hamilton 1797)

Bibliography

Cogan, Jacon Katz. 1996. “The Reynolds Affair and the Politics of Character.” Journal of the Early Republic 389-417.

Hamilton, Alexander. 1797. “Printed Version of the “Reynolds Pamphlet”, 1797.” Founders Online. Accessed September 2, 2026. https://founders.archive.gov/documents/Hamilton/01-21-02-0138-0002.

Hamilton, Caroline V. 2011. “The Erotic Charisma of Alexander Hamilton.” Journal of the American Studies 1-19.

Reynolds, James. 1791. “James Reynolds to Alexander Hamilton, [22 December 1791].” Founders Online. December 22. Accessed September 2, 2026. https://founders.archives.gov/documents/Hamilton/01-10-02-0053.

—. 1792. “James Reynolds to Alexander Hamilton, [3 January 1792].” Founders Online. January 3. Accessed Spetember 2, 2026. https://founders.archives.gov/documents/Hamilton/01-10-02-0080.

—. 1791. “James Reynolds to Alexander Hamilton, 15 December 1791.” Founders Online. December 15. Accessed September 2, 2026. https://founders.archives.gov/documents/Hamilton/01-10-02-0029.

—. 1792. “James Reynolds to Alexander Hamilton, 17 January 1792.” Founders Online. January 17. Accessed September 2, 2026. https://founders.archives.gov/documents/Hamilton/01-10-02-0106.

—. 1791. “James Reynolds to Alexander Hamilton, 19 December 1791.” Founders Online. December 19. Accessed September 2, 2026. https://founders.archives.gov/documents/Hamilton/01-10-02-0045.

Troup, Robert. 1791. “Robert Troup to Alexander Hamilton, 15 June 1791.” Founders Online. June 15. Accessed August 24, 2026. https://founders.archives.gov/documents/Hamilton/01-08-02-0407.

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[1] Latin for Carthage must be destroyed

[2] Reynolds literacy was minimal at best

[3] See letters from James Reynolds To Alexander Hamilton during 1792.