7. Lonie Glieberman

When Bernie Glieberman purchased the CFL's Ottawa Rough Riders franchise for a dollar in 1991, he immediately installed his pint-sized son Lonie to run the team's day-to-day operations. The series of bad decisions that followed stands out even in the CFL's notoriously comical history: Lonie was soon dating cheerleaders, firing staff on a whim, and interfering with roster selection. In one notorious incident, after he left Ottawa to found an inept CFL franchise in Louisiana, Lonie's antique car was impounded after he failed to pay for the scoreboard at the team's stadium.