The Counting House No. 8 — The Check That Started a Duel

A piece of paper signed on Hamilton's own bank unlocked a story 230 years in the making

I bought it because of a novel.

Gore Vidal’s Burr — published in 1973 — is one of those books that lodges in you permanently. Vidal wrote it as a first-person memoir, Burr dictating his life story to a young journalist in the 1830s, looking back on the Revolution, the Vice Presidency, the duel, with the sardonic clarity of a man who has outlived his enemies and his reputation both. The book is fiction, but Vidal did his homework. The Aaron Burr who emerges is not the cartoon villain of American mythology. He is brilliant, charming, financially reckless, and badly misunderstood — a man whose historical reputation was destroyed not by what he did but by who survived him.

I read the novel and could not stop thinking about Burr. I went to his autobiography next, then to secondary histories, then to whatever primary material I could find. And then one day in 1992, leafing through a catalog from a dealer in Concord, New Hampshire, I saw it.

A bank order to pay, dated New York, July 27, 1796. Signed Aaron Burr. Drawn on the Cashier of the Bank of Deposit and Discount of the United States at New York — the First Bank of the United States, Alexander Hamilton’s bank — for five thousand dollars. Payable to J.G. or Bearer.

I bought it immediately.

The Question That Wouldn’t Leave Me

Five thousand dollars in 1796 is not a trivial sum. In today’s terms it represents somewhere north of $150,000. This was not a routine transaction. This was a deliberate, pre-arranged movement of capital — the kind of round number that means someone owed someone something specific, and the debt was now being settled.

I read Burr’s autobiography looking for answers. Who was J.G.? What was the $5,000 for? What was Burr doing in July 1796 that required drawing such a sum on Hamilton’s own bank?

The autobiography gave me nothing. Burr was not a confessional writer. I put the question aside, framed the document, and lived with it for the next thirty years.

The mystery remained open.

The Initials

Research I undertook recently finally cracked it.

J.G. was James Greenleaf.

Greenleaf was one of the more spectacular financial disasters of the early republic — a Boston-born land speculator who briefly seemed destined for great fortune before his empire of debt collapsed entirely in 1797, landing him in a Philadelphia debtors’ prison while his former partners Robert Morris and John Nicholson followed him there within months. Before the collapse, Greenleaf had been everywhere — arranging Dutch financing for Washington D.C. land purchases, partnering with the Financier of the Revolution on vast real estate schemes, moving millions of dollars in notes and mortgages across a fragile early American financial system.

And in 1794, he had partnered with Aaron Burr on 210,000 acres of Adirondack wilderness.

The Angerstein Tract

The land had a complicated history even before Burr and Greenleaf got involved.

A Russian-born London financier named John Julius Angerstein — better known today as the art collector whose paintings formed the founding collection of the National Gallery in London — had purchased the Adirondack acreage through a chain of New York land brokers. There was one problem: New York State barred non-citizens from owning property. Angerstein’s title was legally questionable from the moment he received it.

Into this ambiguity stepped Aaron Burr, who believed he had found a solution. The deed could be redrawn, the title cleaned up, and the land acquired at favorable terms. Burr brought in Greenleaf as a financial partner. The deal was structured with staggered payments — including a specific installment due to Angerstein in London by July 1796.

The month of my check.

Hamilton’s Bank

Here is where the story gets interesting.

The bank on which Burr drew his $5,000 order was not a neutral institution. The First Bank of the United States was Alexander Hamilton’s creation — his signature achievement as Secretary of the Treasury, the centerpiece of his economic program for the young republic, the institution he had fought for against fierce opposition from Thomas Jefferson and James Madison. Hamilton had left the Treasury in January 1795 to return to private law practice, but the bank he built continued operating on Wall Street.

And in July 1796, Aaron Burr walked into that bank and drew five thousand dollars.

The instrument was made payable to J.G. or Bearer — not to James Greenleaf by name. In 1796, Burr was maneuvering in a legally complex, partially concealed land transaction where the deed had been drawn in Greenleaf’s name to obscure Burr’s involvement. Writing only initials on a bearer instrument was deliberate. It kept Burr’s name off the transaction trail. This is how politically exposed men moved money in the 1790s.

The Default

Greenleaf took the money and defaulted anyway.

By July 1796, Greenleaf was drowning. He had mortgaged the Angerstein tract to a New York merchant named Philip Livingston — a transaction that violated the terms of his purchase agreement. He owed millions across a dozen speculations simultaneously. The Angerstein payment came due. Greenleaf could not meet it.

Burr was now exposed. Under the terms of the partnership, he had co-signed Greenleaf’s note to Angerstein. If Greenleaf defaulted — and he had — Burr faced a penalty of £24,000, equivalent to roughly $80,000 in 1796 currency.

After nine months of waiting, Angerstein had had enough.

Hamilton Enters

In March 1797, Angerstein filed suit in the New York Supreme Court.

His attorney was Daniel McKinnen. McKinnen’s counsel was Alexander Hamilton.

Hamilton had just resigned as Secretary of the Treasury and returned to private practice. He was one of the most formidable lawyers in New York. And he was now representing, in open court, the man suing Aaron Burr’s land deal partner — with Burr himself legally exposed to the consequences.

The case moved from the Supreme Court into the New York Court of Chancery. Burr filed injunctions. Burr countersued, arguing Angerstein’s original title was invalid because Angerstein was an alien. The litigation ground on for years, stalling during negotiations, flaring up again as new parties entered, accumulating bad feeling on all sides.

In his own Cash Book — now held in the Hamilton Papers at the Library of Congress — Hamilton recorded on December 16, 1802: “Receipts Dr. Costs (Angerstien) 300.”

He was still working the case six years after it began.

On February 8, 1803, the case was finally dismissed — on motion of the complainant, with the consent of Mr. Hamilton as counsel for the defendant. The entry appears in the MS Minutes of the New York Court of Chancery.

Sixteen months later, on July 11, 1804, Aaron Burr shot Alexander Hamilton at Weehawken, New Jersey.

What the Check Represents

With my brother Mike, I attended the 200th anniversary re-enactment of that duel in July 2004, standing on the same Weehawken bluff where it happened, watching actors pace off the distance that Hamilton and Burr once paced for real. I had owned the check for twelve years at that point and still did not know what it meant.

I know now.

The duel was not caused by this land deal. Historians are clear on that — it was triggered by a letter published in an Albany newspaper reporting Hamilton’s remarks about Burr at a dinner party. But the Angerstein litigation ran for six years in the background of everything, generating what contemporaries described as increasingly bitter feeling between the two men. By 1802, Burr’s enemies were using the case publicly, in print, as evidence of his financial dishonesty and his unfitness for office.

The check dated July 27, 1796, drawn on Hamilton’s bank, payable to Hamilton’s adversary’s land partner, represents the moment the financial machinery of their enmity was set in motion. The default followed. The lawsuit followed. Hamilton’s six years of legal work against Burr followed. The accumulation of grievance followed.

The piece of paper I bought for $245 from a catalog in 1992 was there at the beginning of all of it.

The Document

What I hold is a bank order to pay, written in a clear hand on unlined off-white stock, 3¼” by 5½”. The handwriting at the top establishes the institution: Cashier of the Bank of Deposit & Discount of the U.S. at N. York. Below it, the payment instruction: Pay J.G. or bearer — Five thousand dollars. The date: N.York 27 July 1796. And at the lower right, a signature — Aaron Burr — firm and clear, the hand of a 40-year-old Senator at the height of his powers.

He received 30 electoral votes in the presidential election that autumn, finishing fourth behind John Adams, Thomas Jefferson, and Thomas Pinckney. He was not yet Vice President, not yet a duelist, not yet the man who would be tried for treason in 1807 and acquitted. He was simply a New York Senator drawing a large check on his rival’s bank, paying a debt that would never quite be settled.

The mystery I carried for thirty years has been answered.

The initials are Greenleaf. The land is the Adirondacks. The lawsuit is Angerstein v. Burr, New York Court of Chancery, 1797–1803, Hamilton for the plaintiff. And the check — written on the month the payment came due, on the bank Hamilton built, in the year the whole machinery began to move — is exactly what it looked like the first time I held it.

A beginning.