The Fickle Fate of Tobias Lear
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Written by J. Dennis Robinson


He deserves to be the most famous of all Portsmouth residents, and yet his name is still not widely known. A combination of luck and influence put a Portsmouth, NH boy from the South End smack in the heart of power at the dawn of the American nation. But each time Tobias Lear rose high on the wheel of fortune, his life soon came crashing back to earth. (Full story below) 

He was technically Tobias Lear V, the fifth in his family to bear that name. Tobias Lear (1782 – 1816)  was born into revolutionary times. His father's cousin John Langdon was a businessmen and privateer. A noted Portsmouth patriot, Langdon commanded the raid on Fort William and Mary in 1774, built two warships for naval hero John Paul Jones. attended the Continental Congress, and was an early governor of New Hampshire.

Tobias' father, who worked on the ships Ranger and Raleigh, did not fare so well. A failed shipping venture destroyed his income and created a debt that would plague his only son. His father's tombstone at Point of Graves, the one with the fearsome carving of a human skull, is just down the street from the family home on Hunking Street, now a museum. In his time, Tobias V would rise above the fame of the Langdons and fall below the debt and depression of his father.


Portsmouth Boy Makes Good

Despite moderate means, young Toby managed to attend Governor Dummer Academy and Harvard University in Massachusetts. By 1784, then in his early 20s, he was back in Portsmouth casting about for a career when a family friend received a letter from George Washington. America's "First Citizen" was in need of a private secretary, and this was no small job. A farmer by trade, General Washington had just spent a decade off fighting for the Revolution. The new secretary would have to catch up on the neglected accounting at Mt. Vernon, Washington's 10,000 acre plantation in Virginia. In addition, young Mr. Lear would become tutor to Washington's adopted children and would handle a flood of correspondence. The aristocratic "Farmer" Washington wrote to his Yankee friend describing the job this way:

"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..."



The Tobias Lear Connection in Portsmouth, NH 

Life at Mt. Vernon

Both Lear and Washington were clear and prolific writers. Their letters and journals give us a precise picture of Mt. Vernon. Tobias Lear arrived in Virginia in 1786 and remained when Washington was selected as first president of the United States three years later. True to Washington's word, the young man from Portsmouth became part of the family and intimate with the most famous people of his time. The young secretary attended the Commander in Chief's inauguration in New York City, the nation's temporary capital.

Later, traveling through New England in 1789, Washington made a courtesy call at Hunking Street in Portsmouth, NH where he met the family of Tobias Lear. Mrs. Mary Stillson Lear, mother of Tobias V, soon became a friend of Martha Washington. The Portsmouth-Washington connection grew even stronger when Tobias married Polly Long, his childhood sweetheart. Polly too became an intimate of the first "First Lady" and, when the new US capital moved to Philadelphia, the Lears were part of the presidential household.

Always in-the-know politically, Lear traveled in the elite social circles. He was caught up in the plan to build a new "Federal City" on 100 square miles of swamp land along the Potomac. At the same time, Lear had to balance the President's account books, see to the education of the president's step-children, and oversee domestic matters down to the last piece of furniture. With his salary quadrupled to 800 pounds (the president received 25,000 pounds), Tobias and Polly were successful enough to have a child, Benjamin Lincoln Lear, to whom the president himself was godfather.

By 1792, with Washington considereding a second term in office, Lear was itching to cash in on his influence and go into business like the four Tobias Lears before him. He created Lear & Co. with financial backing from a partner out of Newburyport, Massachusetts. The plan was to profit from the new Capital City, designed to be a thriving port on the Potomac as the country expanded westward. Money from the sale of building lots would theoretically pay for the construction of the great stone government buildings at what was to become Washington, DC.

Lear bought Lot #9 on the river and planned, as one of the nation's first mall developers, to strike it rich by courting foreign investors. With letters of commendation from no less than Thomas Jefferson, Alexander Hamilton and George Washington, Lear was about to sail for Europe to find investors when his wife Polly died. She was among 5,000 Philadelphians killed in a sudden epidemic of Yellow Fever. Three years later Tobias married Frances, the widow of an old friend. In 1796, she died of tuberculosis.

Unlike today, George Washington continued to run his business while in office. Not only did he profit from his farm managed by 400 enslaved Africans, but he also profited from the development of the capital city that was to bear his name. While still running personal and diplomatic missions for the president, Lear kept Washington's personal accounts, brokered his tobacco and farm produce, and served as chairman of the "Potomack Company" that sold Washington, DC real estate.

When the key investors in the real estate scheme defaulted and landed in debtor's prison, Lear retreated to Mt. Vernon. By a twist of fate he was at the farm when the former president suddenly took ill and died in 1799. Lear's stirring eyewitness account of Washington's final hours is one of history's most important journal entries. Lear became embroiled in another scandal when some of Washington's papers went missing, likely destroyed by Lear and Martha Washington at the president's request. The scandal, like his father's debts, dogged Lear to his death.





Haiti & the Barbary Coast

President Thomas Jefferson offered Lear the unofficial position of American consul to Santa Domingo, an island crucial to the "triangle trade" of molasses to rum to slaves upon which much of the economy depended. Moving from the frying pan into the fire, Lear and his son Benjamin arrived in the West Indies just as the black revolutionary Touissant L'Ouverture was at his peak. Fearful that a black independent state would set an irreversible precedent, Napoleon Bonaparte chose this moment in history to send a French armada with 20,000 troops to quell the rebellion. Lear, who had intended to profit from his unofficial, unsalaried position, was forced to retreat to Virginia as the French navy destroyed the capital city and put down the rebellion. Lear spent the next year petitioning the Congress to forgive his mounting personal debts that he claimed were incurred while he was on a patriotic mission for America. He was politely turned down.

At the age of 41 Tobias Lear started over. This time President Jefferson offered him a political plum -- Consul General to the infamous North African coast. It was a dangerous mission, but the salary and expense account were enticing, and Lear was allowed to conduct private business on the side. In 1803 the United States was essentially paying blackmail to the notorious Barbary Coast pirates to prevent them from interrupting American trade.

Lear's luck held for the moment. He married for the third time and prepared to sail for Algeria on the ship USS Philadelphia, changing his travel plans at the last minute to the USS Constitution.  The Philadelphia was captured in the Mediterranean Sea and its nearly 300 crew members held hostage. Col. Lear became the primary figure in the protracted negotiations that lead to the release of the hostages in exchange for a healthy fee in the historic Treaty of Tripoli years later.

The Lears spent nine apparently profitable years at their comfortable home in Algiers. Their job was to keep peace with the local "dey," a man who was known to decapitate those who displeased him, leaving their headless bodies at the palace entrance. In the end, Tobias Lear too fell out of favor when the dey who demanded more than his standard bribe. The Lears were forced to flee their home, grabbing what possessions they could carry onto a ship headed back to the States. The year was 1812 and, as they returned home. President James Madison was declaring  war on England.

Death of George Washington 

Washington In Flames

The last chapter of Lear's life found him back in the thick of things. After a slow re-entry through Virginia and Washington, DC, the Lears found their way past British blockades for a visit to Portsmouth, NH.

Tobias Lear's final post was as secretary to the War Department. He and his beloved third wife Fanny and his son Benjamin, now a lawyer, leased a home just blocks from the White House, soon to be taken over by British forces. As the War of 1812 dragged on, Lear kept the financial books. He complained bitterly that the military was being over-billed by profiteering suppliers. Even as Lear added up the overdue military budget, the poorly defended capital city was attacked and many buildings were burned to the ground by the British.

The war ended in a stalemate in 1815 with neither side gaining any territory. Though apparently wealthy at last, happily married, and auspiciously employed, Tobias Lear V shot himself with a pistol in his garden on October 11, 1816 . He was known to have suffered from severe headaches and bouts of depression. He was endlessly vilified by the media. But it was a curious exit all the same. After a lifetime of prolific writing and scrupulous record keeping, Lear left no suicide note and no official will.  

SOURCE: While hundreds of books have been written about the life of Washington, just one biography is dedicated to the life of Lear. The Checkered Career of Tobias Lear by Ray was published in a small edition by the Portsmouth Marine Society in 1984 and is currently out of print. 

Copyright © 2013 by J. Dennis Robinson, all rights reserved. Robinson’s history column appears in the Portsmouth Herald every other Monday and exclusively online at his independent Web site He is the author of 11 books including UNDER THE ISLES OF SHOALS and AMERICA’S PRIVATEER, available on and in local stores.