Osborn Deignan Osborn Warren Deignan ( February 24 , 1873 – April 16 , 1916 ) was an enlisted sailor and later a Warrant Officer in the United States Navy . He received his country ' s highest military decoration — the Medal of Honor — for actions in the Spanish - American War . Born in Iowa , he joined the Navy in 1894 and participated in the Battle of Santiago de Cuba , the largest naval engagement of the Spanish - American war . Deignan and seven others attempted to block the entrance to Santiago Harbor , Cuba but the Spanish destroyed their ship before they could accomplish their mission , and took them prisoner . The men were later released and Deignan received the Medal of Honor for his actions . He went on to become an officer and served in various posts and ships throughout the Navy until retiring in 1906 . He died in Colorado in 1916 , and was buried in California . Early life . Deignan was born February 24 , 1873 ( as per first Navy enlistment record dated December 7 , 1894 ) near Stuart , Iowa to John Deignan and his wife . His father had also been a sailor , serving in the Navy during the American Civil War , and afterwards went to work for the Rock Island Railway as a conductor . When Osborn was five years old , a torndado struck his father ' s train in Grinnel , Iowa , killing him and leaving Osborn , his mother and his brother to survive on their own . His mother remarried and the family , along with two additional children from his new stepfather , moved to North Tremont Street in Stuart . In 1887 he left school and went to sea , serving on ships in the Atlantic ocean , the Arctic and the Caribbean . Military career . Deignan enlisted in the United States Navy from his home state of Iowa , originally on December 7 , 1894 ( as per first Navy enlistment record ) . He served on numerous USN vessels between 1894 and 1896 and , having deserted from the USS Newark on May 6 , 1896 ( as per naval records maintained by the Military Record Center ) then re - enlistment in 1898 ( as per naval records maintained by the Military Record Center . ) He was assigned as a Coxswain to the during the Spanish - American War . The " Merrimac " had frequent problems with the steering and engines , and Deignan referred to it as " cranky " . After a short time on the ship , he garnered a reputation as an able helmsman and was preferred when delivering coal to the other ships in the fleet , a task that could be difficult in a ship that was already hard to control . When Rear Admiral William 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 " Merrimac ' s " streering 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 through 1904 , 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 , California area . Death and legacy . Deignan died April 16 , 1916 in Cannon City , Colorado at the age of 43 ( based on birth in 1873 ) and was buried with full military honors at Forest Lawn Memorial Park , Glendale , California . His grave can be found in the Whispering Pines section , L - 1165 . Post # 1842 of the Veterans of Foreign Wars was named in his honor . 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 fire from the Spanish batteries , Deignan displayed extraordinary heroism throughout this operation .