10. Hulk Hogan vs Ric Flair - WWF vs World Champion - WrestleMania 8

Vince McMahon's WWE empire stands tall as the most successful wrestling company of all time. Surviving every road block that has been put in front of him, McMahon has beaten all his competition and even the federal government to deliver his vision of sports entertainment that has defined wrestling for the past four decades. But of course, not everything Vince has touched turns to gold. Even the smartest mind in the industry has missed glaring, unbelievably simple and nobody can mess-up opportunities to generate the maximum amount of green the business he essentially owns, can offer. But somehow he does it and on a disturbingly frequent basis. Not even Vince McMahon, the BEST EVER out of making money out of wrestling, made these simplest of money makers into what they could be at the WWE. Here's 10 such examples where his decision making was so off, he might as well have chucked money down the drain...Early on in the Turner Broadcasting era of WCW, they took a while to get used to how wrestling worked. One of their earliest mistakes was hiring a non wrestling fan in Jim Herd to be Vice President. One of Herds first acts as VP was to decide that at 42, Ric Flair was too old, to be a top star. In fact, he wanted to repackage Ric as a roman gladiator called Spartacus, not realising that Flair was actually WCWs biggest draw. After turning down an insulting pay cut, Flair was fired by Herd. What Herd didnt realise was that back then, the titles actually technically belonged to whoever owned them, and Flairs title still represented both WCW and the NWA. Once he heard, Flair picked up the phone to Vince McMahon at the WWF, which ended up with WWF potentially having both of the countries top title belts on their show and a dream feud between both champions, Ric Flair and Hulk Hogan. The original plan was for 1992's WrestleMania 8 to feature the dream match between Flair and Hogan but soon after that was changed to a double main event featuring Flair vs. Randy Savage and Hogan vs. Sid. Depending on who you believe, the story goes that Hulk Hogan was planning to retire at the event, and clashed over losing to Flair. Hogans idea was to go out on top, by pinning Flair cleanly and leaving as World Champion. Vince McMahon disagreed and changed the match. Another school of thought is that, Vince was nervous that the match wouldnt be so special after having already done a house show run or even that he was trying to save the match for WrestleMania 9. Whatever happened, McMahon made the decision to put on a double main event instead, and the dream match didnt happen until both men ended up working for WCW in 1994.For whatever reason, McMahon missed the biggest opportunity of the early 90s. No matter who won the match, Vince would have been able to promote that he had the one true undisputed champion on his roster and show fans that he had the dominant brand. On top of that it was set to happen on the biggest event of the year at Wrestlemania in the Hoosier Dome in Indiana. The WWF made some good use of Flair during his short first tenure, like his matches with Savage and Bret Hart, but he ultimately opted to move back to WCW.