Winn commanded brigades in France during the First World War, and was a recipient of the Silver Star and the French Legion of Honor (Officer).

A native of Winchester, Kentucky, he graduated from the United States Military Academy at West Point in 1888 and was commissioned in the Cavalry Branch.

Winn went on to serve in Mexico during the United States occupation of Veracruz and on the Texas–Mexico border during the Pancho Villa Expedition.

Winn's wartime heroism was recognized with award of the Silver Star and the French Legion of Honor (Officer).

[6] Winn's classmates included several individuals who later attained general officer rank, including Henry Jervey, Charles Hedges McKinstry, William V. Judson, George W. Burr, John L. Hayden, William S. Peirce, Peyton C. March, James W. McAndrew, Charles A. Hedekin.

[12] In March 1899, Winn was with the 2nd Cavalry when it began service at Cienfuegos, Cuba, and he remained with the regiment when it moved to Matanzas.

[14] In April 1907, Winn was detailed to quartermaster duty and assigned to oversee construction at Boise Barracks, Idaho.

[14] In December 1908, Winn was posted as assistant to the chief quartermaster at the headquarters of the army's Central Department, which was based in Chicago.

[16] From December 1913 to August 1914, Winn was again posted to Fort Ethan Allen, Vermont, this time as commander of 2nd Squadron, 2nd Cavalry Regiment.

[16] In September 1914, he was detailed to inspector general duties and assigned to the expeditionary force that took part in the United States occupation of Veracruz.

[16] With the army expanding for World War I, in October 1917, Winn was assigned to Camp Dix, New Jersey as the post's inspector general.

In January 1918, Winn sailed for France after he was assigned as inspector general for the Services of Supply (SOS) of the American Expeditionary Forces (AEF).

He was hospitalized for illness from mid-October until November 15, four days after the Armistice with Germany which ended the war, when he took command of the 157th Infantry Brigade, part of the 79th Division.

[20] Winn's First World War service was recognized with award of the Silver Star and the French Legion of Honor (Officer).

5 (June 3, 1919)[21] In October 1890, Winn married Grace Stanley LeGrow, whose sister Susan was the wife of Brigadier General Robert D.