Olenski played college football for the Alabama Crimson Tide, while serving in the Army at Fort Warren and then professionally with the Miami Seahawks and Detroit Lions.
He also served as a coach for the Alabama Informals football team in their lone 1943 season and at Fort Warren in 1944 and 1945.
[5][6] Olenski was taken in the ninth round as the 78th overall pick in the 1944 NFL draft by the Brooklyn Tigers.
[8][10] With the Seahawks, Olenski played for one of his former coaches at Alabama, Hank Crisp, and was a starter at the tackle position for the duration of the season.
[11][12] After his first season in Miami, Olenski was signed by the Baltimore Colts in July 1947, but was subsequently cut on August 26.