General Charles Paine, was a three time defender of the America's Cup races: 1885 with the yacht "Puritan"; '86 with "Mayflower" and finally in '87 with the boat "Volunteer" -- so named for Paine's division of black volunteers he commanded during the the civil war.
After graduating from Harvard, with the war underway, he joined the army and received a commission as captain in the Massachusetts Infantry. He rose rapidly, serving as colonel on the staff of General Benjamin F. Butler (who also loved sailing and later owned the schooner America) and played a key role in the capture of Port Hudson.
As a brigadier general, Paine commanded a black volunteer division that boasted 14 medals of honor in the 1864 Richmond campaign and then capturing Fort Fisher.
He returned to Boston a Major General.