5. Shawn Michaels
Back in 1998, Shawn Michaels was put as the WWF Commissioner, a portrayed match maker and rules enforcer, eventually joining Vince McMahon’s group of wrestlers called The Corporation as a villain. However, in a segment on Raw is War, Vince McMahon explained his dissatisfaction with Shawn Michaels as Commissioner and even went on to say that he sucks. Mr McMahon was unhappy with the fact that Michaels was holding back The Corporation from intervening in a match between Mankind and Shane McMahon, in which Shane was getting his ass kicked. As a result, Vince McMahon fired Shawn Michaels as Commissioner to which Michaels replied with a sweet chin music to the chairman.
4. Stone Cold Steve Austin
Stone Cold Steve Austin has had many run ins with the chairman, Vincent Kennedy McMahon but one memorable moment was Stone Cold’s first ever stunner to Mr McMahon. This memorable moment featured in a 1997 episode of Raw and saw Austin deliver a stunner to the chairman after telling him that he can kiss his ass. Although it wasn’t the greatest of sells (let’s be honest) nobody ever thought to do anything to Vince McMahon back then which is why this moment is so memorable. Austin was arrested by the New York police soon after he delivered the stunner as part of the segment. Oh yeah, there is also the moment where Stone Cold Steve Austin pretty much gives the whole McMahon family a stunner. In this amazing segment, we witnessed possibly the greatest sell in WWE history… Yep, that’s right you guessed it! Stone Cold Steve Austin’s stunner on Linda McMahon. It’s a thing of beauty!
3. Brock Lesnar
On the January 28th episode of Monday Night Raw in 2013, Brock Lesnar returned after he quit back in SummerSlam to confront Vince McMahon about his decision to fire Paul Heyman. After giving Mr McMahon a romantic nose snuggle, Lesnar then gave Mr McMahon a devastating F5 after Mr McMahon warned Lesnar not to do something he would later regret. According to WWE.com, Mr McMahon suffered a broken left hip that required surgery, however, since it was planned that Mr McMahon was getting hip replacement surgery, the whole thing was most likely a work that was added in the storyline to put over The Beast.
2. Randy Orton
In an episode of Raw back in 2009, Randy Orton was in a segment with Mr McMahon which saw Mr McMahon let Orton know that he made his dad (Cowboy Bob Orton) a superstar. He said that if he had not done that, Randy would not have been here now and probably would have ended up being a gym teacher in St. Louis. The chairman then wanted an apology from Randy and threatened to fire him if he did not apologise. With his patience wearing thin, Mr McMahon had enough and just as he was about to fire Randy Orton, Orton slapped him across the face before delivering a stiff kick to the head. He then gave Mr McMahon a legitimate nasty punt kick across the head which saw the chairman suffer a legitimate concussion. It was revealed backstage that Mr McMahon had actually told Randy to legitimately kick him in the head and he was very pleased with how the segment went. I know! I too am wondering what goes on in that weird twisted head of his… Must have taken a few too many hits to the head…
1. Kevin Owens
On the September 12th episode of Smackdown Live, we saw Vince McMahon return to confront Kevin Owens about his son’s actions. The very same actions that got Shane suspended after he snapped and started brutally attacking Kevin Owens after Owens insulted his kids. Vince McMahon started off by insulting Kevin Owen’s physique and how he got his ass kicked by his son Shane. He then went on to let Kevin Owens know that he has not lost one court battle out of his many due to the fact that he is a billionaire *cough* corruption *cough* Kevin Owens responded by making Vince give his permission to be able to beat a McMahon senseless and he agreed, mindlessly. Owens then viciously headbutted the chairman which busted him open. He then gave Vince a super kick before delivering a frog splash to him from the top apron. You got to give Vince credit, 72 years old and still willing to take bumps for the business he loves!