While a senior at Georgia Military Academy, Pless enlisted in the U.S. Marine Corps Reserve on September 6, 1956, and served with the 1st Motor Transport Battalion in Atlanta. After graduation, he attended recruit training and advanced combat training at Parris Island, South Carolina, finishing in October 1957. He then served as an artillery surveyor with the 10th Marine Regiment, 2nd Marine Division, until September 1958.
While attending flight training at Pensacola, Florida, he was commissioned as a second lieutenant on September 16, 1959. He was promoted to first lieutenant on March 16, 1960, and designated a naval aviator upon graduation from flight training on April 20, 1960.
Pless next served successively as squadron pilot with HMR(L)-262, Marine Aircraft Group 26 (MAG-26), at New River, North Carolina; with HMR(L)-264 aboard the USS Boxer (CV-21) and later the USS Wasp (CV-18); again with HMR(L)-262, Marine Aircraft Group 26, at New River; as Assistant Administrative Officer of HMR(L)-262 aboard the USS Shadwell (LSD-15); and as Squadron Adjutant, HMM-162, Marine Aircraft Group 26, at New River.
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