#4 The Coach gets arrested for betting
In 2001, Vince McMahon's righthand man, Jerry Briscoe, tempted company newbie Jonathan Coachman to enter a $10 football pool. Many other wrestlers got involved and everybody seemed to be having some fun — until the cops showed up.
The police went straight to the Coach and accused him of running a gambling pool and proceeded to cuff him. Vince McMahon rushed to the scene and the police filled him in and told that a $1500 would get the Coach off the hook.
The chairman refused to pay the amount and proceeded to roast the Coach for 45 minutes before the cops took him away.
On the way to the station — with the Coach thinking about the implications of losing his job and landing jail — the cops took a U-turn and returned the Coach to the arena, letting the Coach know that it was a rib orchestrated by Vince McMahon himself.
Needless to say, the future ESPN employee wasn't too pleased with the situation.