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His luck in love, as in business, was rocky at best. Despite his powerful post as secretary to President George Washington, Tobias Lear seemed fated to fail. His first wife Polly died young. His second wife too. Lear committed suicide while married to his third. It is a story tailor made for opera.

Mary Long Lear, known as "Polly", was a Portsmouth girl and Tobias was a Portsmouth boy. Tobias was fresh out of college when he was recommended for the job of bookkeeper and secretary to the most important man in the new United States at his farm at Mount Vernon.

The connection was certainly political. Benjamin Lincoln, father of Lear’s Harvard colleague suggested the young man’s name to Washington. Lear's father was also cousin to the powerful shipbuilder John Langdon, and the Langdons knew the Washingtons. From his first letter to young Tobey Lear, Gen. Washington, hero of the American Revolution, made it clear that his new employee would sit right at the family table and become part of the Washington household.

Almost two decades later Lear was at the President’s deathbed, holding his hand as the most famous man in the nation expired. Lear's account of Washington's final hours is among the most amazing essays in American history. Lear planned the president's funeral and wrote the press releases, despite his own deep personal sadness. Washington had been like a father to him.

Lear had three wives in all -- Polly, Fanny and Fanny. Polly, by all accounts, was a welcomed addition to the Washington household. By the time she arrived, George Washington had come out of retirement and grudgingly accepted the position of President. The American capital was first in New York, then Philadelphia. The Lears lived smack inside the first "white house" where Polly gave birth to Benjamin Lincoln Lear, named in honor of the man who had recommended Lear to his influential job. Baby Ben's godfather was the president himself.

Martha Washington doted on the baby and loved Polly. The two women planned the very first formal functions of the nation's first family, literally inventing the social structure of the new country. Besides his own mother and sister in Portsmouth, New Hampshire, and all his wives, Martha Washington was a powerful force in Lear's life. Martha even became close to Tobias' mother back in Portsmouth.

We tend to picture Martha as that white-haired matronly woman, much like Mrs. Santa Claus, sitting quietly in the cloudy half-finished painting by Gilbert Stuart. What we forget is that Martha was a tough lady, worldly wise and influential. Originally Martha Custis, she was a widow with two children when she married George. Martha's only boy "Jackey" Custis had four children of his own, and then he too promptly died, leaving them to the care of their famous grandparents smack dab in the middle of Revolutionary America.

There is a famous painting of the "Washington Family" from this era by Edward Savage. It's huge and hangs in the National Gallery, depicting an elderly George and Martha Washington posed stiffly across a table with two small children with their black servant. These are the Washington grandchildren, "Nelly" Custis and George Washington Parke Custis. One of Lear's many tasks was to tutor these children, and his letters are rich with the details of domestic life among the Washingtons. One moment Lear was dealing with a national crises, and the next he was off buying stays for Nelly's dress or a new fob for her watch.

In the midst of all this, Polly Lear contracted Yellow Fever while out shopping with Martha in Philadelphia, came home and died at age 23. Thomas Jefferson and Alexander Hamilton were among Polly’s pallbearers. Lear was crushed. His mother back in Portsmouth took baby Benjamin. For Lear, things never quite went right again. He left the safety of the president's household, attempted to act as consul to the West Indies just as Napoleon attacked the islands with 20,000 troops. He masterminded the building of Federal City, a new national capital on the swampy Potomac River later name "Washington", but went bankrupt in the process.

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