Later that year, he joined the Virginia Military Institute, where he developed into captain of Company A, and in 1909 graduated in the upper tier of his class.

Owsley was present in 1919 at the formative caucus meeting of the American Legion in Paris, and was later elected National Commander in 1921, spending his year long term in support of veterans' issues, such as prosecution of war profiteers.

[1] Using official records from Washington, Owsley found that over one hundred thousand war veterans were not receiving adequate financial support.

[2] Owlsey added, "If ever needed, the American Legion stands ready to protect our country's institutions and ideals as the Fascisti dealt with the destructionists who menaced Italy!"

The American Legion is fighting every element that threatens our democratic government — soviets, anarchists, I.W.W., revolutionary socialists and every other 'red' .

"[3]Owlsey's priorities were on display at a San Francisco assembly just before retiring from his head position, where he stated that better hospitalization, rehabilitation, adjusted compensation, and Americanization were necessary for veterans.

Owsley remained in politics, but helping the Texas campaigns of Republicans Thomas Dewey and Dwight D. Eisenhower.