He was a first cousin once removed of Rear Admiral John A. Winslow, who also served in the Civil War and is best known as the commanding officer of USS Kearsarge which defeated CSS Alabama.

Despite enemy fire from point-blank range, which resulted in a bullet wound to his hand, Winslow retained command throughout the engagement.

Winslow was recalled to active duty in World War I with the rank of rear admiral.

While in this assignment, Winslow's flagship was USS Aloha, a private sailing yacht acquired by the Navy for use during the war.

The admiral's younger brother, Arthur Winslow, also joined the Society, representing the General's oldest son, Major Caleb Stark.

Together, they were the parents of six children, three sons and three daughters, including:[1] Admiral Winslow died at his home, 205 Commonwealth Avenue in Boston, Massachusetts, on January 2, 1932.