The "Flying Squadron" was one of the two battle squadrons organized by the Atlantic Fleet in response to the declaration of war on Spain. While the main squadron headed south toward Cuba with a mix of heavy battleships and patrol gunboats, the Flying Squadron ships temporarily stayed back in Hampton Roads in case the Spanish battle fleet decided to attack the American mainland. It was not clear where the Spanish squadron might go, so the Americans had to have fast ships to quickly react to the threat. Because Hampton Roads is the rough geographical center of the East Coast, it was only natural to have the squadron based here. In the end, the Spanish warships steamed for Cuba, and upon hearing this news, the Flying Squadron left Hampton Roads and headed south.
The artist of this work, Carlton T. Chapman, produced a large amount of U.S. Navy artwork. Though he trained at the best art schools in Europe, it would seem the summers spent at his uncle's shipyard in Maine proved to be his biggest influence. He traveled with the Flying Squadron to Cuba as a contract artist and produced several pieces of battle art based on eyewitness views. He also produced several War of 1812 pieces for the U.S. Naval Academy.
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