He dropped out of high school to support his family during the printer's strike against the Chicago Tribune.
[1] Shea took a two-year hiatus from his education to join the United States Army.
In 1958, Shea received a sponsorship from John S. Boyle, the Democratic Committeeman from Oak Park Township, to work as a caseworker in the Cook County Department of Public Aid.
Boyle promoted Shea to assistant state's attorney, and later Director of Research, Planning & Development for the Cook County Circuit Court.
George Ryan appointed Shea the Chair of the University of Illinois Board of Trustees.