"My Dearest, Angelica"

"Indeed my dear, Sir if my path was strewed with as many roses, as you have filled your letter with compliments, I should not now lament my absence from America."

I treasure the Hamilton musical on so many levels. In addition to the wonderful score and fluid lyrics, the story is so well-researched. For example, in Take A Break, Alexander Hamilton and Angelica Schuyler Church express their affection for one another with special attention to grammar.

Alexander writes to Angelica:

My dearest, Angelica
"Tomorrow and tomorrow and tomorrow
Creeps in this petty pace from day to day"
I trust you'll understand the reference to
Another Scottish tragedy without my having to name the play
They think me Macbeth, and ambition is my folly
I'm a polymath, a pain in the ass, a massive pain
Madison is Banquo, Jefferson's Macduff
And Birnam Wood is Congress on its way to Dunsinane

Angelica then writes back to Alexander, and notices his punctuation:

My dearest Alexander
You must get through to Jefferson
Sit down with him and compromise
Don't stop 'til you agree
Your fav'rite older sister
Angelica, reminds you
There's someone in your corner all the way across the sea

In a letter I received from you two weeks ago
I noticed a comma in the middle of a phrase
It changed the meaning. Did you intend this?
One stroke and you've consumed my waking days
It says:

"My dearest Angelica"

With a comma after "dearest." You've written

"My dearest, Angelica."

There is a big difference between "My dearest Angelica" and "My dearest, Angelica."

For some time, I have tried to track down the primary source behind that lyrics. Professor Joanne Freeman at Yale kindly pointed me in the right direction. (Lin-Manuel Miranda received a lot of the Hamilton documents from Freeman's collection of Hamilton papers while he was writing the play.)

Here's what happened.

On October 2, 1787 (a few weeks after the Constitution was signed), Angelica wrote to Hamilton:

Indeed my dear, Sir if my path was strewed with as many roses, as you have filled your letter with compliments, I should not now lament my absence from America: but even Hope is weary of doing any thing for so assiduous a votary as myself.

The comma came after "dear."

On December 6, 1787, Hamilton wrote back to Angelica. At the time, things were busy. The day before, Hamilton published Federalist #17, and the following day, Delaware became the first state to ratify the Constitution.

You ladies despise the pedantry of punctuation. There was a most critical comma in your last letter. It is my interest that it should have been designed; but I presume it was accidental. Unriddle this if you can. The proof that you do it rightly may be given by the omission or repetition of the same mistake in your next.

I wish I could write like that.

On November 8, 1789 (about a month after the Judiciary Act of 1789 passed), Hamilton wrote to Angelica:

Adieu Dear Angelica! Remember us always as you ought to do—Remember us as we shall you

Your ever Affect friend & brother

And on February 4, 1790 letter, Angelica replied, calling Hamilton "dear friend" with friend emphasized.

Adieu my dear Brother, remember me affectionately to Eliza. I have this moment received her letter, and have received three from you.4 I accept this attention on your part as I ought, and if in return I cannot give you any agreeable information, I can at least give you the History of my Mind, which is at present very much occupied by a very great, and very amiable personage. Adieu my dear friend.

A. Ham. got friend-zoned!

This mystery was unriddled.