#3. Vince personally loans Ric Flair money
"Nature Boy" Ric Flair is nearly as well known for his poor handling of money as he was for his amazing handling of opponents in the ring. According to his own admission, he spent a fortune trying to maintain the lavish lifestyle he portrayed on television. That, and a number of divorces under his belt, has led to a lot of financial trouble over the years.
According to a 2016 appearance on the 'Stone Cold Podcast" with Steve Austin, Flair revealed that McMahon himself had loaned the former WWE champion quite a bit of money over the years.
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“He’s always been there. When I’ve had financial woes, through my divorces, he’s lent me money... One time, I was into him for $800,000... He said, ‘I wouldn’t lend my kid this kind of money.’" - Transcript by Complex.com
Flair said he always paid the money back, including using his WrestleMania XXIV check to pay off the aforementioned $800 grand.
It just goes to show you how far McMahon will go to help someone he respects in need.