Pillman graduated from Norwood High School in Norwood, Ohio, a suburb of Cincinnati. While attending Miami University in Oxford, Ohio, Pillman played football for the Redskins (now RedHawks) as a defensive tackle where he set records in the "tackles for loss" category. Pillman struggled academically and needed help with school to continue to play; he was then tutored by Miami rugby player Bill Minnich. A two-time Second Team All-American, he went undrafted by the National Football League, joining the hometown Cincinnati Bengals as a free agent in 1984 (where he won the Ed Block Courage Award for his team) and later the Canadian Football League for the Calgary Stampeders in 1986. Pillman also played for the Buffalo Bills in preseason action in 1985, but he was the last player cut before the start of that season. His attempts to make the roster of the Bengals were covered in a series of articles in The Cincinnati Enquirer. Pillman and John Harbaugh, current head coach of the Baltimore Ravens, were roommates and defensive teammates while at Miami.
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