The sovereignty of the new American Nation was tested early in the 19TH Century as, in the shadow of the Napoleonic Conflict between France and England, American merchant shipping became the primary neutral force in the world. Two of the principle causes for the hostilities which led to the War of 1812 were the desertion of British sailors to the better pay and conditions of American ship, and the British Naval search and impressment of American citizens to serve on their war ships.

A bloody yet decisive American victory was found on September 5, 1813, when the U.S.S. ENTERPRISE of 16-guns fell in with British Naval Brig BOXER of 14-guns off Pemaquid Point, Maine. Both the American captain, Lieutenant William Burrows, and British Captain Samuel Blyth led their respective crews into the engagement, and Blyth was mortally wounded in the first salvo, and Burrows would fall soon after, leaving both ships in the hands of junior officers. Edward McCall would complete the victory for ENTERPRISE, leading the captured ship into Portland. Both captains would be given burial honors side-by-side in the city's Eastern Cemetery, and Blyth's sword was sent home.

A finely detailed and composed work of art, Bentham-Dinsdale skillfully captured the courage on display and the mortal effects of the combat action, with the ships showing their shared distress. After several early victories, the war had begun to look more dismal, so the American press took this victory and ran with it, pushing for a decisive result. They have it the following year, not long after the Battle of Lake Erie.