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Winfield Scott Schley was the commander of the U.S. Navy's"Flying Squadron" until it was united with the "North Atlantic Fleet" under Admiral Sampson. At the Battle of Santiago, Schley was the commander of the U.S naval forces present, and fought the battle from his position aboard the BROOKLYN.

Biography:

Winfield Scott Schley was born near Frederick, Maryland. His uncle, Henry Schley, served under General Winfield Scott in the war of 1812, thus the reason for his being named after the famous general.   Another uncle also fought under Scott in the war with Mexico when the future admiral was only a young boy.

The descriptions of Schley are interesting and varied.  The following apparently describeshim very well.
 

"Schley was a very active and mischievious boy, but well liked by all of those who knew him.  In his adulthood, he was a jolly man, fond of a joke, and warm-hearted.  He loved children.  He was always fair, and he put strangers at ease at once.  He was easily approached, and had a quick and alert manner.  He was a fighter by instinct.  He was resolute, resourceful and daring, quick to decide in an emergency, and confident in himself.  It would always be his instinct in battle to take the offensive, to strike the firstblow."  His step-mother said of him “he is a man of very pleasant and amiable character, always in good humor and never out of temper”.

Schley was a young, but bold and plucky officer when he served on one of the blockade ships in the Civil War.  After the Civil War, in 1865, he suppressed a riot of 400 Chinese on one of the Chincha  Islands. Later Schley landed in La Union, San Salvador  because of an insurrection and took possession of the Custom House to protect American interests.  In 1867, he was acting assistant professor of Spanish at Annapolis, and later became head of the foreign languages department.  He spoke Spanish fluently.  In 1871, he landed marines in Korea while searching for a missing American Ship, the GENERAL SHERMAN, believed to have been plundered by pirates sanctioned by the Korean isolationist government.  He led this landing himself. After serving in the Orient, Schley served another four years at Annapolis, then three years in the South Atlantic, one year in Washington, and four years in the Lighthouse Service.

From 1876 to 1879, Commander Schley  commanded the USS ESSEX in the South Atlantic, and in the waters around Mexico.  In 1876,  he punished pirates in the lower Congo.  Later, as a reward for settling a quarrel in Liberia, a native King wished to bestow one of his wives on him.  “Owing to the contrary laws of my country”, Schley tactfully explained that he felt  “obligated to decline.”

Once, the “MABEL CLARK,” a merchantman, had been shipwrecked on Tristan da Cunha. Schley was sent to pick up survivors.  One member of the merchant vessel's crew, Marcus Johnson, had fallen in love with the granddaughter of the local governor and did not wish to leave because he wanted to marry her.  There being no minister on the island, Schley was asked to officiate at the wedding.  The couple went  aboard the ESSEX and were married by Schley.

In 1884, he volunteered to rescue lieutenant Greeley who met trouble while exploring the Arctic regions.  It is said that on this rescue mission some of Schley’s officers  protested that he was taking serious risks with his ships.  He replied,  “Gentlemen, there are times when it is necessary to take risks.  This is one of those times." Amazingly, Schley successfully located Greeley and his group in the vast frozen wasteland and brought  the living survivors, as well as the bodies of the dead, home.

In 1887, Schley was promoted to captain.  He became the commanding officer of the cruiser BALTIMORE in 1889.

In 1891, Schley was still in command of the USS BALTIMORE when she was sent to Valparaiso, Chile, to protect American interests in that country during a rebellion.  There were extremely bad feelings between the Chileans and the Americans.  Two American sailors from Schley's vessel were killed on shore, and others wounded during riots, leading to problems which very nearly developed into war between the United States and Chile.  Schley positioned his ship in such a manner as to train his guns on the Chileans and practically dared them to start a fight.   Because of his willingness to fight, he apparently did not have to do so.  After some time of confrontation, the hostilities were finally concluded when Chile agreed to pay reparations for the dead and wounded American sailors.

Commodore Schley took command of the “Flying Squadron” in March, 1898 at Newport News, Virginia.  The squadron at that time included the cruiser BROOKLYN, which became Schley’s flagship, and the battleships MASSACHUSETTS and TEXAS. The captain of the BROOKLYN was Captain Francis A. Cook.

When Schley took command of the “Flying Squadron,” it is said that he went to the President and pleaded to meet the Spanish fleet in the Atlantic when they were heading for Cuba.  He pointed out that their approach to U.S. shores was an act of aggression, and he was willing to fight them.  Of course, he was held back and the battle did finally occur, but at the Bay of Santiago rather than in the Atlantic.

On May 13, 1898, the Flying Squadron left Hampton Roads enroute to Cuba.  As it left Hampton Roads, the squadron consisted of the BROOKLYN, TEXAS, MASSACHUSETTS, SCORPION, and the collier, MERRIMAC.  By May 25, the battleship IOWA, under command of Captain Robley Evans, the MARBLEHEAD, VIXEN, and the EAGLE joined the squadron. On May 26, however, Schley ordered the EAGLE to proceed to Key West because she was too slow to keep up with the squadron.

From the time the "Flying Squadron"  left Hampton Roads, Schley was searching for the Spanish fleet.  There were many contradictory reports from different sources concerning the location of the Spanish fleet. In addition, the orders from Rear Admiral Sampson were also confusing and contradictory.  Schley, using his best judgement continued to search for the Spaniards.  At the same time, he had problems coaling his ships, with storms at sea, and with the constant breakdown of the collier MERRIMAC.

It was finally determined that the Spanish fleet was in Santiago Bay.  Schley’s squadron arrived there on May 29, 1898.  Schley reconfirmed that the Spanish fleet was in Santiago himself and then formed a moving blockade at the entrance to the harbor to prevent the Spaniards from slipping out and escaping.

Because of the narrowness of the channel into the bay, it was determined that the Spanish fleet would have to come out one ship at a time, thus providing an advantage to the blockading fleet.  As they waited, the ships of the fleet periodically fired on Morro Castle and other fortifications on the coastline.  It was Schley’s idea to try to incite return fire from the Spaniards so as to determine the range of their guns.  He succeeded in doing this.

On June 1, 1898, The NEW YORK arrived with Rear Admiral William T. Sampson  on board, along with the OREGON and several colliers.  Previously, Captain Sampson was promoted to Rear Admiral, with the battleship NEW YORK, as his flagship, and was placed in command of the North Atlantic Squadron. As senior officer, Sampson assumed command of both the ":Flying Squadron" and the North Atlantic Squadron, which were combined into a single force.

After five weeks of waiting, blockading, and bombardment of the fortifications, smoke was spotted in the harbor.  The Spanish ships were firing up their boilers and apparently preparing to leave the harbor to make an attempt to escape.   The MASSACHUSETTS was gone, having left for Guantanamo to recoal.  The main line of the blockading ships consisted of the BROOKLYN, NEW YORK, TEXAS, OREGON, IOWA, INDIANA, MARBLEHEAD, GLOUCESTER, VIXEN, SUWANEE, DOLPHIN and PORTER.

At 9:45 am on July 3, 1898, the Spanish ships, under the command of Admiral Cervera, began coming out of the harbor in single file.  First was the MARIA TERESA, followed by the VIZCAYA, CRISTOBAL COLON, OQUENDO, FUROR and the PLUTON.  Strangely enough, shortly before, at 8:30 AM, without explanation, the NEW YORK with Admiral Sampson aboard, left the area and disappeared over the horizon. Unbeknownst to Schley, Sampson was off for a meeting with army commander, General Shafter.
 
As the MARIA TERESA was passing through the channel from the Bay, the first shots fired were from the IOWA under the command of  Captain Robley D. Evans.  She was located close to the entrance, and was able to inflict damage to each of the Spanish ships as they passed by.  The Spanish fleet concentrated fire on the BROOKLYN in an apparent attempt to destroy her first as she was believed to be the fastest American vessel present.  However, although outgunned, the BROOKLYN fought back in a very effective manner.  As the battle became desperate, out of the smoke came the OREGON followed by the TEXAS.  The MARIA TERESA was the first to be run ashore, then the OQUENDO  was pummeled, set on fire, and headed toward shore to go aground and surrender.

The VIZCAYA was finished off by the GLOUCESTER and the IOWA and except for the CRISTOBAL COLON, all of the other Spanish ships were defeated.  The COLON, being a much faster ship than any of the American ships on paper, except perhaps the NEW YORK which was not there, and the BROOKLYN, which unfortunately had two of its engines uncoupled thereby not being capable of its top speed, was making good speed away from the pursuing ships.  It was noticed by Commodore Schley that the COLON was hugging the shoreline and would eventually have to turn seaward to clear Tarquino Point.  With this in mind, the BROOKLYN took a straight line course toward Tarquino Point.   Coming within gun range of the COLON, the BROOKLYN and the OREGON both began firing on the ship.  The large guns of the OREGON made some very near misses on the COLON, and the BROOKLYN landed several shots  near the waterline of the COLON, when, at 1:15 pm,  she struck her colors and surrendered.

At 1:45 pm, the NEW YORK returned with Rear Admiral Sampson on board, intercepted the BROOKLYN's launch with the surrendering officers from the COLON on aboard, and received their surrender on board the NEW YORK.

The battle was over, the Spanish Fleet was destroyed.  Commodore Schley and the BROOKLYN were in the thick of the battle.  Although Sampson was the commander-in-chief and received most of the credit, while the actual battle was fought and directed by Commodore Schley.   Schley took no credit for himself, but gave honor to the captains and men under him.

On July 11th and 12th, the INDIANA, TEXAS, BROOKLYN, and NEW YORK fired on the city of Santiago to induce the city to surrender. The city surrendered on  July  14, 1898.

On the 14th of August, the fleet was ordered home, arriving in New York Harbor on the 20th of August  to a triumphant reception, with most of the attention being directed toward the BROOKLYN and its Commodore Schley.   At this homecoming, Schley was promoted to Rear Admiral.

On October 9, 1901, on reaching the statutory age of sixty-two, Schley was placed on the retired list.

On October 2, 1911, Schley fell dead while walking on the streets of New York City.  He was buried in Arlington cemetery with the honors that he so richly deserved.
 

Graham, George Edward, Schley and Santiago. Chicago: W. B. Conkey Company,  1902

West, Richard S. Jr.,  Admirals of American Empire.  Indianapolis: The Bobbs - Merrill Company, 1948.

Young, James  Rankin, History of our War with Spain. Harrisburg, PA: The Minter Company, 1898.