A divorced 47-year-old who describes himself as a 'degenerate gambler' isn't everyone's picture of success, but Barstool Sports founder Dave Portnoy is exactly that to his loyal army of supporters.Thanks to nearly 5 million followers across social media as well as his wildly popular website, Portnoy is reportedly worth more than $100 million and boasts luxury properties in exclusive locales like Nantucket and the Hamptons.Along the way, Portnoy has faced constant criticism over accusations of misogyny and unfair labor practices. He's crashed media day, protested NFL commissioner Roger Goodell, and as a result, has been banned from attending league events. More recently, Portnoy raised eyebrows last month by Presidential nominee at 299 after recently supporting his Republican primary rival, .
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