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The Sex Scandal of Alexander Hamilton


By Brendan Wilson

2020 has been awful for people not named Elon Musk.  We’re living through a terrifying global pandemic, an economic meltdown, and social isolation.  Now, we’re being dragged kicking and screaming into another election cycle.  Against our collective will, we’re bombarded with misleading polls, lectured by opinionated uncles, and, of course, force-fed details of the latest political sex scandals.

In 2016, the faces of Stormy Daniels and Karen McDougal were splashed over every grocery store checkout. In the run up to November 3rd, additional accusations of lewd behavior on the part of the president will likely arise from other sources.  It goes beyond Trump - Katie Hill was forced to vacate her Congressional seat after admitting to an affair with a staffer in 2019.  Pro-life Congressman Tim Murphy was forced to resign in 2017 after demanding his mistress get an abortion.  Who on Earth could forget about Anthony Weiner’s Twitter feed?  Sex scandal has become ingrained in American politics like fatty fair food at the Iowa Caucus.  But like deep-fried butter sticks, it is bad for us. Let's face it, it is ugly business.

The American sex scandal is on the uptrend, but just because it seems like a recent phenomenon does not mean that all pre-Lewinsky politicians were able to resist the temptations of the flesh. Though it wasn’t in our history textbooks, everyone knows of JFK’s amorous connection with a certain busty, blonde bombshell. It was widely believed that FDR philandered with several women while married to his cousin, Eleanor. Woodrow Wilson allegedly had an extra marital affair while in office . We can go back further still, to the first sex scandal in our nation’s history.

In the early 1790's, Alexander Hamilton was at the zenith of his career.  Having been born a poor bastard son of a “fallen” woman in the far-off Caribbean, he was able to gain power and influence through sheer force of will and an insatiable desire to improve himself.  In short order, he had become a war hero, helped draft and ratify the Constitution, passed his debt assumption plan through Congress, and created a central bank.  In 1791, he was settled in Philadelphia serving as Treasury Secretary and preparing his famous Report on Manufactures.

That summer, Hamilton’s wife, Eliza, boarded a boat with their four children bound for her father’s mansion in the relatively cool climate of Albany.  Eliza Schuyler was a woman of high society, born to a family with a good name.  She took a gamble marrying the penniless immigrant with no pedigree or inheritance, but she loved Alexander blindly, supporting him in every cause.  She should have known that she was leaving a fox in a city full of hens.  

Hamilton was a reputed flirt.  His biographer, Ron Chernow, tells us that John Adams scoffed at his “indelicate pleasures.”  An appalled Harrison Gray Otis recounted Hamilton’s “liquorish flirtation” with married women at a dinner party.   First Lady Martha Washington even named her feral cat after him!  It has also been written that Hamiliton enjoyed Philadelphia’s risqué parties frequented by scantily attired women with exposed arms and cleavage.  Abigail Adams derided the clothing worn at these parties, “The style of dress … is really an outrage upon all decency...”.  

It was in this setting that Maria Reynolds arrived unannounced at Hamilton’s home to plead for his assistance.  She told him that her abusive husband had left her penniless to run off with another woman.  She implored him to spare her, a fellow New Yorker, some money so that she may return to live with her friends.  Softened by the damsel in distress and eager to play the role of hero, he agreed to bring some cash to her boarding house later that day.

Upon arrival, he was “shown upstairs, at the head of which she met [him] and conducted [him] into a bedroom.”  It was evident after some conversation that something “other than pecuniary consolation would be acceptable.”  Though we don’t have any photos of Mrs. Reynolds, Chernow admits in his detailed account of the affair that “she must have been very alluring.”  The tom cat could not resist.  Thus, began the Reynolds affair.

Hamilton would later admit that he “had frequent meetings with her” for months, most of them in the bed he shared with his wife.  He eventually met Maria’s husband, James Reynolds, and quickly sized him up as a scoundrel.  Smelling foul play, Hamilton sought to distance himself from the potentially dangerous couple.  But as he did so, she regained his attention with letters describing her husband's abuse or, more seriously, his intention to inform Eliza of the whole affair.  In describing the hysterical nature of the letters, Chernow explains that they “should have alerted [Hamilton] that he was dealing with a perilously unstable woman.”  Sensing danger, Hamilton began sending letters to Eliza encouraging her to stay in Albany and requesting that she alert him should she decide to return home early.

In the fall, Hamilton received an indignant letter from James Reynolds feigning outrage at having learned of the affair.  He made it clear that he was now “determined to have satisfaction.”  After a meeting, Hamilton agreed to pay Reynolds $1,000 in two installments to keep a tight lid on the matter.  Hamilton resolved that this was a logical place to end the affair, but Reynolds had other plans.  Eager to keep the golden goose close, he encouraged Hamilton to continue visiting his wife as a “friend.”  After several pleading letters from Maria, Hamilton obliged, seeing Maria until the summer of 1792 while paying James small hush money “loans.”

The same year, James was arrested for his involvement in a scheme to defraud Revolutionary War veterans.  In jail, he told Senator James Monroe and two congressmen of his involvement in illegal speculation with none other than the Treasury Secretary of the United States.  Monroe and the congressmen confronted Hamilton at his home.  Hamilton vehemently denied the charges of corruption, clearing himself by admitting to the extra-marital affair and providing the letters to prove his innocence.  Monroe was satisfied but kept the letters as evidence should the matter arise again.

Over the years, Hamilton left government to practice law.  Maria divorced her husband (Aaron Burr was her attorney).  In 1796, Hamilton wrote an article attacking the private life of his political nemesis, Thomas Jefferson, intimating that he had had an affair with one of his slaves.  Above such trash talk, Jefferson deployed his attack dog, James Collender, who ran a story accusing Hamilton of speculating on securities with government funds and engaging in a licentious affair with a woman below his standing.  He printed the Reynolds letters as supporting evidence.  Shocked, Hamilton blamed Monroe for the leak, who was so offended at the charge that the two nearly fought a duel.  In a bit of extraordinary historical irony, Aaron Burr intervened to diffuse the tension and avoid bloodshed.

Hamilton knew that the only way to salvage his public image was to destroy his private life.  In 1797, he settled in a boarding house to pen 91 pages that would exonerate him from charges of corruption while admitting to the sordid affair with Maria Reynolds.  Before long, nearly every literate American had read the document that would become known as The Reynolds Pamphlet. The affair, along with his savage attacks on John Adams in the run up to the election of 1800, rendered Hamilton political persona non grata in American politics, wiping out any chance of him becoming president and effectively destroying the Federalist Party.

It is unlikely that hot mics on Billy Beane buses will bring down any political parties this election season.  The shock of a political scandal depends on how divergent the alleged behavior is with our expectations.  Was anyone really surprised after reading Stormy Daniels' account?  Looking back on the other side of the aisle, knowing the track record of the man involved, can we really say that we were astonished when the Monica Lewinsky scandal broke? Were we shocked by Anthony Weiner's repeated indiscretions? Having just broken free of the corruption and excess of the British monarchy, voters in our early republic demanded leaders of integrity and moral standing. Generally speaking, we seem to expect less now.  Fortunately, increasing gender equality and the reach of social media will likely embolden people to hold the powerful accountable for past sexual indiscretions. Unfortunately, this means that we have not seen the last of the sex scandal in American politics. 

Chernow, R. (2017). Alexander Hamilton. London: Head of Zeus.

Hoffman, E. C. (2017). The Hamilton affair: A novel. New York: Acarde Publishing.

Pruitt, S. (2018, April 20). The Scandal That Ruined Alexander Hamilton's Chances of Becoming President. Retrieved September 11, 2020, from


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