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RE: Evander Holyfield is extremely broke

The fight was an obvious money grab. I often wonder why those closest to these athletes at their peak don't help them with better financial advice; some even actively swindle them. I don't know if I should feel sorry for someone that lived so irresponsibly. I do hope he bounces back though and has learnt his lesson...well, he's a little too old to do otherwise

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While I haven't watched all of it, the TV show Ballers that stars the Rock as an agent of sorts showcases exactly this. I know it is a fictional show, but it may as well be a documentary.