From the 1830s to 1965 Castle Williams on Governors Island served as a military prison. Over the years prisoners have attempted to escape by swimming across the Buttermilk Channel to Red Hook.

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The New York Times Tuesday, AUGUST 29, 1901

ESCAPED BY SWIMMING Prisoner on Governors Island Makes a Dive for Freedom. Supposed to Have Been Picked Up by Passing Tug—Third Escape of Notorious Deserter.

Ex-Private George Harvey of the Second Cavalry. United States Army, who, up to 3 o'clock yesterday afternoon, was a military prisoner on Governors Island, and who is notorious throughout the service as a deserter, escaped yesterday by swimming half way across Buttermilk Channel, where he Is supposed to have been picked up by a passing tug. It was the third time that Harvey has eluded the vigilance of the authorities. All the afternoon and last night a squad of men, under Sergt. Way, the Supervisor of Castle Williams, were searching for the escaped prisoner in Brooklyn, where he is supposed to be in hiding. That he was picked up by a tug was vouched for by several civilians, who averred that they had seen the man when he jumped into the water, and had watched his subsequent movements up to the time he was fished out and carried away. They did not get the name of the tug.

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Text of article from Long Island Star Journal, August 29, 1939

"Astoria Soldier Wins Medal For Drowning Rescue"

While away on maneuvers with his company, John W. Skiffington of Astoria, U. S. Army private, today received notice that he had been awarded the coveted Soldier's Medal by the War Department for rescuing a man in New York Harbor on June 13.

Skiffington, despite a strong ebb current and other hazards, leaped off the Governors Island retaining wall and pulled ashore one of three privates who had attempled to escape from disciplinary barracks in Castle Williams, on the island.

The soldier saved was Raymond H. Jackson, 22. The two other prisoners, captured later in Brooklyn, were Robert M. Flint, 29, and Edward R.. Knox, 18.

According to the citation, Jackson had stroked only I50 yards from shore when he found himself unable to swim farther and started shouting for help. The cries were heard by the Astoria soldier. "Private Skiffington" reads the War Department communique, "voluntarily plunged into the bay with utter disregard for his personal safety.

"After reaching the exhausted and drowning man, Private Skiffington fought his way back against a strong ebb tide and towed him with great difficulty to shore. The heroism displayed by Private Skiffington on this occasion reflects great credit upon himself and the military service."

The Soldier's Medal is awarded only for outstanding bravery in peace time. Besides, It carries a $2-a-month increase in pay. Skiffington usually is stationed at Fort Jay, Governors Island. His outfit, Company K, 16th Infantry, at present is at Plattsburg.