In the nearly 200 years that pro wrestling has been around in one form or another, the sport has not seen anyone who was as creative and as revolutionary as Vince McMahon. It doesn't matter if you go 200 years into the future... you still probably won't find anyone who has contributed to the business and has shaped it in such a way as Vince has. That is his legacy, he has earned every bit of it, and nobody can ever take that away from him. However, as is the case with anybody in any line of work throughout all of recorded history, it hasn't always been rainbows and butterflies for "Mr. McMahon". Wrestling fans have seen him make quite a few boneheaded mistakes, both in kayfabe and out. Some have cost him a lot of money, while others have seen him receive endless amounts of laughter and ridicule. Some of those mistakes even cost him fans and viewers, as people were so upset that they would stop watching the WWF/WWE product. This article will take a look at some of his biggest mistakes, in and out of the televised wrestling product we see every week. Only the worst of the worst decisions matter here, so let's get this one underway.