Leonard registered for the draft in Covington, KY on 30 June 1942.

He was one of five men from the Cincinnati area inducted into the Amy at Fort Thomas, Newport, KY on  26 October 1942.that were specifically slated for the 508th PIR, Camp Blanding, FL.

On 17 December 1942 Pvt Estep was transferred from Camp Toccoa, GA to Co I, 508th PIR.

On 30 March 1943,. Pvt Estep was transferred to the Parachute School, Fort Benning, GA,

Leonard married Agnes Duncan in Morgan, OH.

He was discharged on 24 October 1945.

The marriage date preceding his release from active duty may imply that he was home on convalescent leave.