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Col. Tobias Lear V, known as Toby to his friends, left his mark on the early history of the United States as an in-law and the personal secretary to George Washington. He also authored the only firsthand account of the death of the nation’s first president.

His journal is his legacy, but his story is one of determination, failure, upheaval, poor judgment and eventual self-destruction.

Young Tobias Lear

Tobias Lear was born on Sept. 19, 1762, to the respectable Portsmouth, N.H., couple of Capt. Tobias Lear IV and Mary Stillson Lear. As a young man, Toby attended the Dummer Charity School and then Harvard College.

Capt. Lear was a prosperous Portsmouth farmer and sea-trader until 1776, when the British Navy confiscated his ship, the Polly. Capt. Lear had paid for the Polly’s cargo, a consignment of New England goods and lumber bound for Antigua. The total loss of the Polly nearly bankrupted the Lears.

But despite their financial hardship, the captain and his wife made paying for Toby’s Harvard College tuition a priority. He graduated in 1779.

Tragic Figure

Historian P. Bradley Nutting, emeritus at Framingham State College, considered Tobias Lear a tragic figure. Wrote Nutting:

He had the natural inclinations of a diplomat, preferring negotiation to confrontation. While ambitious, Lear was also compassionate, deeply affected by human suffering.

Tobias Lear also liked being seen as a person of importance. For example, he used his title of colonel, one that he received when President John Adams appointed Washington as commander in chief of the army in preparation for war with France. Lear never saw combat nor did the nation go to war with France, yet Lear used the title the rest of his life.

Lear’s historic relationship with George Washington began when he came to Mount Vernon in 1785. The general, four years after the Revolutionary War ended, needed a new secretary. As an active citizen on the young nation’s stage, the future first president was flooded with correspondence and requests.

So Washington reached out to his friend Maj. Gen. Benjamin Lincoln for help. Lincoln, who became the namesake of Lear’s son, recommended his 23-year-old friend Tobias Lear. Washington wrote in a letter to Gen. Lincoln:

I have at last found a Mr. Lear, who supports the character of a gentleman and a [Harvard] scholar. He was educated at Cambridge, Mass. He has been to Europe and in different parts of this continent. It is said he is a good master of languages. He reads French and writes exceedingly good letters.

Mount Vernon

Lear’s primary duties were letter writing, but he also helped Washington manage the day-to-day operations of Mount Vernon. According to author Stephen Decatur, in the Private Affairs of George Washington,

Besides handling all the financial details, supervising the instruction of the [Washington] children, and managing the household, he was in charge of correspondence, penning most of the personal and confidential letters that the President did not write himself, issuing invitations for the weekly dinners, and superintending the necessarily voluminous files.

In addition to Lear’s time at Mount Vernon as an employee, his second and third marriages brought him into the Washington family.

Tobias Lear’s first wife was his childhood sweetheart Mary “Polly” Long. They married in 1790. Together they had a son named Benjamin Lincoln Lear.

Washington Marriages

Polly went to work for the Washingtons when the family moved to Philadelphia. Sadly, she died in the 1793 yellow-fever epidemic.

Lear then married Frances Bassett Washington, a widow of George Washington’s nephew George Augustine Washington. She died in 1796 of tuberculosis.

His third marriage was to Francis Dandridge Henley, or Fanny, Martha Washington’s niece.

Lear’s second and third marriages transformed him from a key employee to a beloved member of the family. This new connection gave Lear nearly unlimited access to the Washingtons and the Mansion House Farm.

The Death of Washington

When Lear was at Mount Vernon he was able to record in his journal Washington’s last words and his death on Dec. 14, 1799:

“Have me decently buried; and do not let my body be put into the vault in less than three days after I am dead.” I bowed assent; for I could not speak. He then looked at me again and said, “Do you understand me?  I replied yes! “Tis well” said he.

About ten minutes before he expired (which was between ten & eleven o’clk). he breathing became easier; he lay quietly; he withdrew his hand from mine, and felt his own pulse. I saw his countenance change, – I spoke to Dr. Craik, who sat by the fire; he came to the bedside. The general’s hand fell from his wrist I took it in mine and put it into my bosom. Dr. Craik put his hands over his Eyes and he expired without a struggle or a sigh!

Lear’s Mysterious End

Lear’s life ended quite differently from Washington’s. He died neither in his bed nor surrounded by friends and family. Lear committed suicide.

Tobias Lear and his wife spent his last evening with their friends, Cmdre. and Mrs. Rogers, in the Federal City. The Rogers’ daughter later wrote:

My father and mother had been making a late visit to the Lears [sic] one evening, and, as they were bidding goodbye, Mr. Lear said, “I will walk with you, Commodore, a little way.” He accompanied them, slowly strolling and talking; at last they were home, he stopped and said, “Goodbye, Mrs. Rogers! Goodbye, Commodore!” Pressing my father’s hand warmly.

The next day after breakfast, on a warmer-than-normal morning, Tobias Lear walked into the garden of his home with a loaded pistol and shot himself in the head.  He did not leave a note or will. Sometime later his body was discovered by his adult son Benjamin. The Rogers’ daughter added to her description of Lear’s death:

The very next morning my parents were sent for. Something terrible had happened at Mr. Lear’s. He had killed himself soon after leaving my father. My mother always fancied that he wished to say something to my father, which her presence prevented; and they both remembered his farewell to them had been more tender and lingering than usual, [sic] However he died and left no sign. There was not a conjecture even of the cause of his death. He seemed well and vigorous, quiet and self-contained, but not unhappy.

(Ms. Rogers seems to have been confused about the timing of Lear’s death. The Washington City Gazette wrote that Tobias Lear killed himself the following morning in his garden, not after he left her parents that evening.)

Why?

Today, more than 200 years after his tragic end, we do not know what led Tobias Lear to take his own life. But a series of questionable decisions at least offers context.

In an effort to make his own mark after Polly died in 1793, Lear tried to breathe financial life into his company. T. Lear & Co. invested in land and sold staples like flour even as the national economy was collapsing.

During Lear’s financial troubles, he continued to assist with rent collection on Washington’s properties. Yet, in a moment of desperation, Tobias Lear stole Washington’s rent money from an Alexandria property. On discovery of the theft, Washington was livid:

You will perceive buy [sic] the enclosed manner that I am disappointed in receiving the rent for my house in Alexandria. These things put you, the payer and myself in an awkward situation; for it must seem strange what has been paid. I must therefore, request, in explicit terms, that you will receive no more moneys due to me; and I should be glad to have a statement of the A/c [accounts] as it stands between us, since the last was rendered. … I have not the slightest doubt of my being credited for every farthing you receive on my A/c; but that does not remedy the evil. … [It] would be uncandid and inconsistent with the frankness of friendship, no to declare that I have not approved, no cannot approve, of having my money received and applied to uses not my own, without my consent.

Another Scandal

Luckily for Tobias Lear, Washington forgave him, which spoke to the friendship and love that Washington had toward him. Nevertheless, one wonders how this event might have lingered in Lear’s memory.

Another scandal might have contributed to his eventual self-destruction. It was associated with his mentors George Washington and Thomas Jefferson, Washington and Jefferson regularly corresponded about a variety of subjects, including the appropriate balance of federal and state power.

Washington, who held the Continental Army together under the weak Articles of Confederation, saw the need for unified states under a federal umbrella. Jefferson, on the other hand, wanted a government resting on strong state and limited federal power.

Historians hypothesize that Jefferson rebuked Washington for his overly monarchical presidency, and Washington more than likely defended himself, but we do not know for certain. For some reason their letters after the summer of 1796 have not been found.

The Missing Letters

One clue about where the letters went came from Tobias Lear:

A few days since Colo Humphreys called upon me, and informed me that in a public company, dining at Mr Ames’ at Dedham, on Saturday, the Revd Mr. Krikland of Boston said he had been informed that I had suppressed certain papers belonging to the late Genl Washington, and [were] in my charge for some time after his decease, particularly some of the Genls’ Diaries, for the period when Mr Jefferson was Secy of State, and that those papers were essential to the History of the Generals’ Life now preparing for the press.

Firestorm

Historian Ray Brighton believes Tobias Lear destroyed multiple letters in order to protect Washington’s and Jefferson’s reputations. A letter from Lear to Alexander Hamilton supports this hypothesis. He wrote, “There are, as you well know, among the sev[eral] letters and papers many which every public and private consideration should withhold from further inspection.”

When Washington’s papers were found to be missing, Lear was accused of theft. The scandal—an early American version of a relentless social media attack—seemed endless. Massachusetts state Sen. Timothy Pickering, a fanatic Federalist and secretary of state to both Washington and Adams, wanted to destroy Tobias Lear,

…as part of the bitter rearguard action the Federalists were fighting against the march of Jeffersonism; that he was still persisting as late as 1829….”

In order to protect and help Lear, President Jefferson appointed him to be the US envoy to Saint-Domingue, modern-day Haiti. Jefferson and Secretary of State James Madison also appointed him to be the nation’s peace envoy to North Africa during the Barbary Wars of the early 1800s.

No Pinnacle

Tobias Lear should have reached the pinnacle of his diplomatic career after negotiating and signing the Tripoli peace treaty with the country’s ruler, Bashaw Yousef Caramanli. The treaty ended the Barbary War—but again Lear set himself up for scandal.

Lear agreed to a secret protocol left out of the final June 4, 1805, draft giving Yousef four years to comply. Nutting notes:

Writing to Madison on July 5, Lear made no mention of the gentleman’s agreement, only commenting ambiguously that it was a “condition that time be allowed for the delivery of the family [American hostages].” … Regardless of Lear’s motives, which he never explained, this clandestine understanding when combined with the agreement to lay ransom [for the American prisoners] would ultimately demolish his reputation in the United States.

Man Without A Party

When the provision was discovered, the Federalists branded him a turncoat and the Democratic Republican Party disowned him. Tobias Lear was then a  scandalous—and partyless—man with little chance for a lucrative political appointment or high-profile diplomatic post.

As a result, he could only get a job with the War Department as an accountant, a position beneath his experience and talents. Lear’s awareness that his professional career would never be what it once was must have contributed to his death.

In the end, historians have a handful of unanswered questions that, if known, would tell us why Tobias Lear committed suicide.

Why did Lear think that stealing from Washington was prudent, and why did he destroy Washington’s and Jefferson’s letters? Why did Lear keep a key part of his North African treaty a secret? And how did he feel about his menial job?

Taken individually, these are difficult issues and powerful experiences for anyone to live with. Throughout his life, Tobias Lear tried to muster his talents to make his name in finance and public service, despite his failures. He tried to build a fortune, maintain a respectable reputation and grasp fame, though he never succeeded.

Conceivably, these might have been factors in his death, but historians can only speculate. Nevertheless, on that September morning in 1816, Tobias Lear gave in and in a time of emotional and mental confinement chose not to embrace the new day.

End Notes

The author of this story about Tobias Lear, Cameron L. Kline is an educator, lecturer, and communications professional living in Philadelphia, PA. In partnership with the Historical Society of Pennsylvania, he was the first scholar to annotate the complete Tobias Lear Journal. 

Note: The material  about the death of Washington is from The Tobias Lear Journal, housed in the archives of the Historical Society of Pennsylvania. It was first fully annotated by the author of this essay. The 70-pages detail the death of Washington, the president’s final wishes, perpetrations and funeral, entombment, plan to reanimate his corpse, the possible publishing of his papers, love for his family, his appointment and voyage to be Council to St. Domingo.

Thanks also to “Colonel Tobias Lear and the Tripolitan Hostage Crisis,” by Bradley P. Nutting in the New England Journal of History and “Private Affairs of George Washington,” by Stephen J. Decatur. 

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

This story last updated in 2022.