[4][5][6] Beginning in 1993 he worked for ten years as a uniformed and plainclothes officer for the Joliet police,[3] winning the Martin S. Murrin Labor Award in 1995[4][7] and serving on the executive board of the local affiliate of the Fraternal Order of Police.
After earning his law degree, he became an Assistant Corporate Counsel for the city of Chicago and worked on a task force prosecuting narcotics crimes.
[12] In 2023, he lost his bid for a third term to Terry D'Arcy[13] During his time as a law enforcement officer for the Joliet Police Department, O'Dekirk allegedly faced seven suspensions totaling forty-nine days as punishment stemming from undisclosed actions.
[14] On May 31, 2020, O'Dekirk assaulted two Black Lives Matter protesters on Jefferson Street in Joliet.
Videos of the incident, which became viral shortly thereafter, showed O'Dekirk grabbing a protester's neck with both hands, pushing him behind a police vehicle, and throwing him to the ground.