After Winfield Scott Schley's graduation from the U.S. Naval Academy in 1860, he served as a midshipman on an expedition to China and Japan. During the Civil War, he served first in the Western Gulf Squadron, where he participated in the capture of Port Hudson, Louisiana, in 1863, and later in the Pacific Squadron. He was promoted to lieutenant in 1862 and lieutenant commander in 1866.
Schley taught at the Naval Academy from 1866 to 1869 and again from 1872 to 1875. Between the two stints at the academy, he served in the Asiatic Station and participated in the U.S. Korean Expedition in 1871. He was promoted to commander in 1874 and served in various capacities in Europe, on the coast of Africa, and in the South Atlantic. Among his commands were USS Essex, USSBaltimore, and USS New York.Schley was also assigned to several posts in the Lighthouse Bureau and served as chairman of the Lighthouse Board in 1897-1898.
In 1884, Schley commanded a relief operaton to rescue Lieutenant Adolphus Greely's trapped Lady Franklin Bay Expedition in the Arctic after several others had failed. Traveling through 1400 miles of ice, Schley and his crew succeeded in rescuing Greely and six of his companions. Schley co-wrote a book about the rescue in 1885.
Schley was commissioned as a commodore in 1898. At the outbreak of the Spanish-American War, he was placed in charge of the Flying Squadron, commanding the flagship USS Brooklyn. Admiral Sampson, his superior officer as head of the North Atlantic Squadron, sent him in pursuit of Spanish Admiral Cervera, first to Cienfuegos and then to Santiago de Cuba. Schley at first declined to go to Santiago but ultimately found his way there and assisted Sampson with a blockade of the harbor to trap the Spanish fleet. On July 3, the Spanish ships attempted to evade the blockade while Sampson was ashore. After a near collision between the Brooklyn and another U.S. ship gave the Spanish fleet an opportunity to escape, Schley's squadron pursued and defeated Admiral Cervera and destroyed the Spanish ships.
Sampson's victory message made no mention of Schley's role, and in fact Sampson believed that Schley had been insubordinate and careless. The public, however, viewed Schley as the hero of the Battle of Santiago de Cuba. In 1899 Schley was commissioned as a Rear Admiral and given command of the South Atlantic Squadron. He retired from active duty in 1901.
Also in 1901, at Schley's request the Navy convened a court of inquiry, comprised of Admiral George Dewey and two other admirals, to investigate charges made against Schley for his conduct before and during the Battle of Santiago. The majority found that Schley had engaged in misconduct and shown poor judgment, but recommended that no action be taken. Admiral Dewey, however, issued a minority report praising Schley and giving him credit for the victory. Although the findings of the majority went against Schley and were ultimately upheld by the Secretary of the Navy and by President Theodore Roosevelt, the publicity of the court of inquiry enhanced Schley's status as a war hero.