8. Eddie DeBartolo Jr. is accused of gambling.

Year of Fine: 1999
Estimated Total Fine: $1 million*
Professional sports leagues typically withhold fines from players, coaches, or owners until evidence of wrongdoing is shown. Pleasing guilty and skipping the protracted trial process is a lot easier for people like former 49ers owner Eddie DeBartolo Jr.

Eddie DeBartolo Jr. is revealed in a gambling scandal by Tim Mosenfelder via Getty Pictures.
In 1999, DeBartolo Jr. entered a guilty plea for his involvement in a gambling scam centered in Louisiana. In addition to handling the legal aspects of the criminal allegation brought against him, the NFL penalized DeBartolo, a junior, $1 million. Eddie, you’ve learned that crime doesn’t pay.