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John McWilliams 1898 Tampa, Florida (standing on right in white shirt)

The 21st regiment fought in the Spanish–American War in 1898. On 22 June 1898, the regiment fought in the attack on Santiago. On 1 July, the regiment was positioned on the left flank of the attack on San Juan Hill. The regiment helped capture the heights on 1 July after fierce fighting with Spanish troops. The Spanish troops surrendered on 16 July. Due to disease issues, the 21st Infantry was withdrawn from Cuba on 23 August.

He enlisted in the Army in 1893 and after this battle fought in the Philippines, in Mexico pursued Pancho Villa, and in France and marching into Germany, all as part of the 6th Infantry. Rising to rank of Captain during WWI.