The Mysterious Death of Tobias Lear

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Tobias Lear meticulously recorded the details of George Washington’s death, but was strangely silent about the events leading to his own.

As Washington’s personal secretary and confidante, Lear scrupulously chronicled the events of his own remarkable life, and yet he left some things unexplained.

Perhaps there are clues to his strange death in the story of his life. He knew four presidents, failed at land speculation, lived well in Algiers, wrote the first history of Washington, D.C., took a honeymoon aboard the USS Constitution and paid tribute to pirates. He married two of Martha Washington’s nieces.

George Washington liked, trusted and respected him, and we owe much of what we know about his personal life to Tobias Lear.

Tobias Lear, Secretary

Tobias Lear was born in Portsmouth, N.H., on Sept. 19, 1762, the son of a shipmaster turned farmer (the farm was located at the present site of Wentworth By The Sea).

He graduated from Harvard in 1783 as the American Revolution ended. He traveled in Europe and throughout the British colonies. In 1784, a family friend of the Lears and the Washingtons, Gen. Benjamin Lincoln, recommended Tobias Lear as tutor to Martha’s grandchildren and secretary to George. Washington offered this job description:

Mr. Lear…will sit at my table, will live as I live, will mix with the company who resort to the house, will be treated in every respect with civility and proper attention. He will have his washing done in the family, and may have his stockings darned by the maids…

It was a big job. He had to catch up on Mount Vernon’s accounts, neglected after Washington spent a decade at war, and reply to a flood of correspondence.

After arriving in Virginia in 1786, Lear soon became Washington’s friend and right-hand man. When Washington was elected president in 1789, Lear moved with the family to New York, then to Philadelphia when the capital moved.

Lear married Mary Long in 1793. They had one child, Benjamin Lincoln Lear, and Washington acted as godfather. Mary died three years after their marriage.

Tobias Lear then married Frances Bassett Washington, George’s niece, in August 1795. Washington gave them a house and 360 acres of his Mount Vernon estate. The marriage lasted seven months, as Frances died of tuberculosis in March 1796. Lear was devastated.

Business Ventures

He rejoined the Washington household, serving as the president’s secretary throughout his first term and submitting his expense reports to Congress. At the beginning of Washington’s second term, Lear left to start his own company and to work with Washington’s Potowmack Company to build a canal around the waterfalls in the Potomac River (now Great Falls Park). Lear lost money on the venture.

As his finances worsened he continued to work for Washington. He once collected rent from one of Washington’s tenants and kept the money himself. Washington was furious with Lear when he found out, but forgave him.

Lear also kept funds from a business partner for months and feigned illness to avoid repaying him. He eventually confessed, apologized and agreed to pay him back.

In late 1799, Lear visited Washington when the former president died. He recorded his famous diary entry:

About ten o’clock, Saturday December 14, 1799, Washington made several attempts to speak to me before he could effect it, at length he said,—”I am just going. Have me decently buried; and do not let my body be put into the Vault in less than two days after I am dead.” I bowed assent. He then looked at me again and said, “Do you understand me?” I replied “Yes.” “Tis well” said he.

Those were his last words.  Lear followed Washington’s wishes to a T, even measuring his body at 6 feet 3.5 inches long and 1 foot 9 inches across the shoulders.

Washington left Tobias Lear a lifetime interest in Walnut Tree Farm. He spent the next year sorting through Washington’s papers, some of which went missing. Lear was accused of destroying the papers, including letters that could have damaged Thomas Jefferson.

To Africa and Back

Despite his bequest from Washington, Lear was still struggling financially. Jefferson did him a favor and appointed him to two potentially lucrative posts: American commercial agent in Haiti in 1802 and consul general to North Africa in 1804.

Before leaving for North Africa, Lear married Martha Washington’s niece, Francis Dandridge Henley. To the end of his life, he doted on Fanny.

While they sailed to Algiers on the USS Constitution, pirates seized another ship, the Philadelphia, and nearly 300 souls aboard. Lear negotiated their release in exchange for a substantial sum in the Treaty of Tripoli.

He was vilified for mishandling the negotiations.

The Lears spent nine profitable years in Algiers. Then Tobias fell out of favor with the dey, who had a habit of beheading people he didn’t like. Just as the War of 1812 broke out, the Lears fled to America.

President James Madison gave Tobias a job as a secretary to the War Department, and he leased a house in Georgetown.  He lived there with his beloved Fanny and his son Benjamin, now a lawyer.

He was apparently wealthy, happily married and well employed.

Or was he?

Lear suffered from headaches and depression. He was dogged by accusations about Washington’s papers and the Treaty of Tripoli. He had only reluctantly accepted his job as chief accountant for the U.S. War Department, having hoped for a Cabinet post.

On Oct. 11, 1816, Tobias Lear shot himself in the head with a pistol. His son Benjamin found him in his Georgetown home, the bloodied gun still in his hand. No note was found, nor did Lear leave an official will.

The mystery of his death remains to this day.

This story was updated in 2022.

Image: Tobias Lear House By John Phelan – Own work, CC BY 3.0, https://commons.wikimedia.org/w/index.php?curid=15203288.