In 1792, the city of Charleston, South Carolina, commissioned from John Trumbull a portrait of George Washington for its city hall to commemorate the president¹s visit the previous year. General Washington sat for Trumbull in Philadelphia in 1792, and this painting was the result.

The commission had personal significance for Trumbull, for he had served as Washington¹s second aide-de-camp during the Revolution. Trumbull chose to convey the critical moment of Washington's leadership during the Revolutionary War when his night maneuvers at Trenton, New Jersey, led to a decisive victory at Princeton the following day, a major turning point of the war. Trumbull considered this portrait the "best of those which I painted." In Trumbull's blend of history painting and portrait, the commander in chief epitomizes heroism and nobility, yet Charleston refused to accept it on the grounds that they preferred a more amiable and peaceful image. Trumbull produced another likeness of Washington, this time with the city in the background, which Charleston accepted.