Having begun an affair with blonde twenty-three-year old MARIA REYNOLDS (1768-1832) in the summer of 1791, when his wife Elizabeth Schuyler Hamilton (pictured) and their children were vacationing in Albany with her family, Alexander Hamilton received this note from Maria in December. Her husband had returned and quickly saw an opportunity to blackmail Hamilton.

I have not tim to tell you the cause of my present troubles only that Mr. has rote you this morning and I know not wether you have got the letter or not and he has swore that If you do not answer It or If he dose not se or hear from you to day he will write Mrs. Hamilton he has just Gone oute and I am a Lone I think you had better come here one moment that you May know the Cause then you will the better know how to act Oh my God I feel more for you than myself and wish I had never been born to give you so mutch unhappiness do not rite to him no not a Line but come here soon do not send or leave any thing in his power.

Although, at that time, Hamilton’s actions were grounds for a duel, James Reynolds chose to ask for money instead. For $1,000 Reynolds proposed to leave his wife to Hamilton and depart the city taking his daughter with him. Hamilton would not or could not come up with such a sum but gave Reynolds money in small amounts while the affair continued. Apparently Reynolds was satisfied with this arrangement. Maria wrote to Hamilton again.

I have kept my bed those tow days past but find my self mutch better at presant though yet full distreesed and shall till I se you fretting was the Cause of my Illness I thought you had been told to stay away from our house and yesterday with tears I my Eyes I beged Mr. once more to permit your visits and he told upon his honnour that he had not said anything to you and that It was your own fault believe me I scarce knew how to beleeve my senses and if my seturation was insupportable before I heard this It was now more so fear prevents my saing more only that I shal be miserable till I se you and if my dear freend has the Least Esteeme for the unhappy Maria whos greateest fault Is Loveing him he will come as soon as he shall get this and till that time My breast will be the seate of pain and woe

P. S. If you cannot come this Evening to stay just come only for one moment as I shal be Lone Mr. is going to sup with a friend from New York.

When Reynolds subsequently tangled with the law—having committed forgery—and was imprisoned, he called upon Hamilton for assistance. When Hamilton refused, Reynolds released information about the affair and also suggested Hamilton had been involved in financial improprieties when he was Secretary of the Treasury. Rather than have his professional conduct impugned, Hamilton opted to admit to the affair with Maria and deal with the personal repercussions of a sexual scandal. Of course, he broke off his relationship with Maria.
Over time, Hamilton paid more than $1000 in blackmail to James Reynolds to keep the affair secret. Maria eventually divorced her husband; Aaron Burr was her attorney.

See this ARTICLE for more information. The portrait of Elizabeth Schuyler Hamilton is by Ralph Earl (1787) and is at The New-York Historical Society.