T. Sampson requested volunteers for an extremely dangerous mission, there were more than enough volunteers, but he chose Osborn as the helmsman. The mission was to sink Merrimac at the entrance to Santiago Harbor, Cuba in an effort to block it and pen the Spanish Navy in the harbor. Seven other members of the crew were also chosen for the assignment. While the crew was attempting to fulfill its mission, Spanish forces fired on the ship and, in the process, disabled the Merrimacs steering controls before the crew could complete their task. The ship sank without obstructing navigation, but the crew was able to escape the ship before she went under. They were rescued by the Spanish and were taken as prisoners-of-war. A month later the Spanish fleet was destroyed at the Battle of Santiago de Cuba and the crewman were released. For his "extraordinary heroism" during the operation, Deignan was awarded the Medal of Honor. On April 9, 1900, Deignan was promoted to the Warrant Officer rank of Boatswain. As an officer, his initial assignments were in the Philippines, first at Manila, then at the Naval Station, Cavite. After meeting her at a party in 1898, he married Maud Huntoon on May 14, 1902, and together they had a daughter. In June 1902, he reported for duty on the and later that year transferred to the receiving ship , at the Mare Island Naval Shipyard, California. He was stationed at Navy Yard, Pensacola, Florida, from 1903–04, and then was assigned to the receiving ship , at Norfolk, Virginia. He remained there for less than a year before reporting for his last tour of duty on the monitor in April 1905. He retired on April 21, 1906, and moved to the Los Angeles area. Death and legacy Deignan died on April 16, 1916, in Cañon City at the age of 39 and was buried with full military honors at Forest Lawn Memorial Park, Glendale, California. Post #1842 of the Veterans of Foreign Wars was named in his honor. Awards Medal of Honor Sampson Medal Spanish Campaign Medal Philippine Campaign Medal Medal of Honor citation Rank and organization: Coxswain, U.S. Navy. Born: February 24, 1873, Stuart, Iowa. Accredited to: Iowa. G.O. No.: 529, November 2, 1899. Citation: In connection with the sinking of the U.S.S. Merrimac at the entrance to the harbor of Santiago de Cuba, 2 June 1898. Despite heavy