#5 UFC
Many years ago Shane McMahon saw that the Ultimate Fighting Championship, an upstart MMA promotion, was starting to gain some steam. He decided to pitch the idea of purchasing the company to father Vince, who unfortunately didn’t see much value in the idea.
Fast forward well over a decade, and the UFC is now worth over $4 billion. In the most literal sense, McMahon cannot even make a bid without being laughed at because the money just isn’t there anymore. While it still doesn’t seem like anything he’d ever be interested in, Vinnie Mac certainly missed the boat in a big way.
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