Alexander Hamilton’s Affair a Grand Mess

Alexander Hamilton was obsessed with his reputation.  As Treasury Secretary, he did everything possible to maintain the integrity of the office.  He was detailed, almost to a fault, with the records.  Every “i” was dotted and every “t” was crossed.  Nothing untoward interested Hamilton in the slightest.  The mere thought of impropriety was anathema to him.

His entire professional career was, almost without exception, lived above reproach.  When there was suspicion of wrong-doing, it was always unfounded.

So it comes as something of a surprise that Hamilton displayed such incredibly bad judgement when it came to Maria Reynolds.  The wife of James Reynolds (an acquaintance of the Secretary), Maria was 11 years younger than Hamilton.  She came to him as the distressed spouse of an abusive husband and mother of a young daughter.  Her desperation likely resonated with Hamilton who, as the son of a “fallen woman”, felt a greater sympathy to her plight as he remembered his mother’s struggles.

She asked for some money, and he offered to bring some by her home in the evening.  He would recount the events later when he penned, “…I put a bank bill in my pocket and went to the house.  I inquired for Mrs. Reynolds and was shown upstairs, at the head of which she met me and conducted me into a bedroom.  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.”

It doesn’t take much imagination to figure out what, in 18th-century language, was being described here.

And so began an affair that lasted the better part of 3 years.  It only took a few months for Hamilton to realize he was making mess of things and try to extricate himself.  But James Reynolds was having none of it.  He truly was abusive and he was a rake, but he was also calculating and knew the Treasury Secretary was in a bad position.  Rather than fly into a rage or demand a duel, James began extorting Hamilton, threatening to expose the affair to Eliza (his wife) while essentially forcing him to maintain an illicit relationship.  Mr. Reynolds had become a pimp, and his wife the prostitute for hire.

Alexander Hamilton clearly knew he was in danger, but his weakness for women, his appetites, the obvious lure of Mrs. Reynolds, and her husband’s threats served to keep him hooked.

James wrote ridiculous letters, saying things like, “…you have acted the part of the Cruelist man in existence.  you have made a whole family miserable.  She ses there is no other man that she Care for in this world.  now Sir you have bin the Cause of Cooling her affections for me.”  Blackmail was Reynolds’ strong suit, grammar not so much.

In mid-December, Hamilton and James Reynolds met face-to-face, and the Treasury Secretary was informed that one thousand dollars would go a long ways to healing a husband’s “wounded honor”…not to mention keeping Eliza Hamilton out of the loop.

The following week, on December 22, 1791, made the first blackmail payment to James Reynolds.  He would make another a couple of weeks later.

Alexander Hamilton was a tremendous thinker and visionary, but his terrible decisions regarding Maria Reynolds would serve to sully his good name.

Recommended Reading: Alexander Hamilton