Tobias Lear was a Harvard graduate and native of New Hampshire. In 1786 he became GW’s secretary upon the recommendation of Benjamin Lincoln. He accompanied the president to New York in 1789 and remained in GW’s service until mid–1793 when he left to pursue his own business affairs. Lear returned to Mount Vernon as GW’s military secretary in 1798 during the Quasi-War with France and remained until GW’s death. Lear was also a merchant in the Federal City and president of the Potowmack Company.

Tobias Lear was married twice. His first wife, Mary Long Lear, had died in 1793. In early August 1795, Lear married Fanny Bassett Washington (Columbian Mirror [Alexandria], 6 Aug. 1795), widow of GW’s nephew George Augustine Washington, who had also died in 1793.