3. Mike Brown
TEAM (YEAR PURCHASED): Cincinnati Bengals (1991)
W-L (WINNING PCT): 113-204-1 (.355)
COMPLEX SAYS: Everyone knows the Bengals suck. For young'ns it may seem like they've always sucked, but that isn't the case. The Bengals made it to Super Bowl XVI in 1982, Super Bowl XXIII in 1988, and remained an AFC contender before Mike inherited the team from his father, Paul Brown. Like father, like son? Hell no! Since Mike's takeover, the Bengals have accomplished shameful feats like 14 consecutive losing seasons and only two playoff appearances over a two decade period. The Bengals have also become known for their rap sheets rather than their stat sheets, and Carson Palmer would rather retire than put on the stripes again. You blame dude?