Jonathan Trumbull was elected governor of the Connecticut Colony in 1769 and became the first governor of the State of Connecticut in 1776. He was also a successful merchant, managing his affairs from this house. Many meetings took place in his home during the years of the American Revolutionary War (1775–1783), as well as in the adjacent War Office. The War Office was originally connected to the house by a secret passage, and it functioned as a major logistical center for the northern states.

A troop of French Army cavalry was stationed on the Lebanon Green during the winter of 1780–1781, and these troops joined those of the Comte de Rochambeau when he marched through in 1781 on their way to join George Washington and the Continental Army prior to the Siege of Yorktown.

John Trumbull was born in the house June 6, 1756. He served as an aide to George Washington in the war and became an artist. He was commissioned by Congress in the 19th century to paint four of the eight historical paintings that adorn the United States Capitol rotunda. He also painted portraits of many of the war's military leaders.