Then his life hit a brief updraft. Two years after Polly's death, Lear married Frances Bassett Washington, "Fanny" for short. The bond was a political masterstroke. Fanny was recently widowed, left with a small child named Mary. Her first husband was none other than Augustine Washington, a nephew of George Washington. Fanny was also Martha Washington's niece. As a wedding gift, the Washingtons gave the Lears a gorgeous property called River Farm in Virginia that, like Mount Vernon and Lear's House in Portsmouth, are still open today to visitors.

Tobias Lear was in the catbird seat again. Then Fanny, who may have contracted tuberculosis from her first husband, died suddenly. Then George Washington, Lear's surrogate father, caught cold and died within a 48 hour period. Entrusted with the Washington presidential papers, Lear immediately fell into a new scandal when some of the papers came up missing. He was accused of conveniently misplacing letters that favor Thomas Jefferson. It was a stain on Lear’s honor that never came clean.

Then followed a twist right out of Ripley's-Believe-It-or-Not. Martha had another niece who was also called "Fanny." So Tobias married again, this time to the young Frances Dandridge Henley. The new President Jefferson appointed Lear consul to Algeria. In the early 1800s the Barbary Coast was a political hot spot, and Lear's job was considered quite a plum, though a dangerous plum. The pirate leaders were not averse to cutting of the heads of people whose peace offerings were considered too stingy. Leaving young son Ben again with Gramma Lear, the newlyweds spent their transatlantic honeymoon aboard the USS Constitution. This ship was later known as "Old Ironsides." Fanny and Tobias were gone nine years.

Things, as always, eventually went sour for Tobias Lear. He negotiated the famous treaty on the "shores of Tripoli" which effectively paid off the bribes of the Barbary Pirates. He was accused of taking a percentage of the fee, which he probably did since making a few bucks was then considered a perk of the consul's job. Branded as a "sell-out" by some politicians, Lear's payments weren't enough to please the pirates, so he was kicked out of Algeria as well.

Arriving back in the newly completed capital, Lear took a job as Secretary of War, just as the British attacked and burned Washington, D.C.. In October of 1816 Lear went into his Virginia garden with a pistol and shot himself. Fanny Henley Lear outlived her troubled husband by 40 years and died in 1856.

In the end, Tobias Lear's greatest loss may have been his self-respect. His greatest love, arguably, was George Washington himself. The man the nation revered almost as a god had treated Lear like a son, then left him all alone to find his way in a world too harsh for a mere mortal to bear.