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#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.
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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.
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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.
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