November 9, 1997 wasn’t just the day of The Montreal Screwjob, it was also the day that for a lot of fans, Vince McMahon was outed as the owner of the company. Unless you kept up with the backstage news, up until this point Vince was “just a commentator.” But thanks to the night and the rise of Stone Cold Steve Austin, McMahon not only found a character, he found the heel character. The evil boss that anyone and everyone could rally against.
But the Rattlesnake wasn’t the Chairman’s only target over the years. Over the years, the boss has pulled some stuff that any real boss would be in prison for decades for. Here’s the 10 Worst Things Vince McMahon Ever Did (On Screen As A Performer).
10 Had Linda Committed
Not only was Mr. McMahon a lecherous and cantankerous old vile man, he mistreated his entire family, at just about every turn. After gallivanting around Monday Night Raw with the buxom bombshell, Trish Stratus, he got in Linda’s face and demanded a divorce. But that wasn’t evil enough, so McMahon claimed that Linda had suffered a mental breakdown and had her committed and kept her heavily medicated.
9 Fought Stephanie
In 2003, Vince was at his most ridiculous. Openly courting and cavorting around with Sable and basically doing whatever he wanted. With no Stone Cold to keep McMahon in check, Stephanie of all people felt compelled to try and reign dear old dad in.
But after going against his wishes, McMahon challenged Stephanie to a match instead. An inter gender match, against his own daughter; in an “I Quit” match - the image of Vince choking her out with a lead pipe is pretty gross.
8 Challenged The Almighty
As a big game hunter, Vince loves to target his enemies’ biggest weaknesses. When the Chairman came up against Shawn Michaels, he came after HBK’s integrity and newfound faith in the Lord. At Backlash 2003, Vince would team up with his son Shane to take on Shawn and God, being portrayed as just a bright white light. It was ridiculous, sacrilegious, and hilarious all at the same time. The promos especially, which saw Vince head to Church to talk to his “opponent.”
7 Dr. Heiney
Imagine if you had your boss openly mock you and an operation that you had to have. It’s bad enough that Vince would often humiliate Jim Ross every change he got, but then Mr. McMahon decided it would be great fun to mock the colon surgery that Jim Ross needed. With “Nurse Slobberknockers” at his side, Vince as Dr. Heiney proceeded to yank all sorts of JR-related items from his derrière up to and including BBQ sauce and even his own head.
6 Fakes His Own Death
The real-life circumstances ruined the “Who Blew Up Vince McMahon” storyline, the eventual end result was ruined. Instead, the Chairman who apparently wanted off TV and had explained to his team “I can’t be on TV if I’m dead” had to scramble to find a resolution to the storyline. That resolution was a simple and petulant need to see who really cared about him.
5 Worked With Undertaker
For months, the Undertaker had seemingly gone insane and started sacrificing superstars and kidnapping and sacrificing both Ryan Shamrock and Stephanie McMahon. It was all in an effort to gain control of WWE.
The Lord Of Darkness had even burnt his symbol on the McMahon lawn and handed Vince the charred remains of Stephanie’s teddy bear. In the end, it all proved to be the ultimate ruse. Taker had revealed he’s been doing all of these terrible acts in the name of a Higher Power, which turned out to be Vince himself.
4 Cheated On Linda
In real life, the Chairman has admitted to not being the most faithful of husbands. Linda has seemingly always forgiven him. Would Linda still forgive Vince if Mr. McMahon openly made out with the girl all over Smackdown and Raw, right in front of her? That’s what happened several times on the show. First, the guys cavorted around with Trish Stratus (much more on her later), not to mention having his fun several years later with the returning Sable.
3 Recreated The Screw Job
When the Montreal Screwjob had actually happened, there was real life tension in the locker room and the industry and it all helped to create the Mr. McMahon character in the first place. Recreating those events one year later was all part of an expertly crafted storyline (by Vince Russo of all people) that played with the lives of both Stone Cold and Mick Foley. Foley, as Mankind was sure that he was Vince’s new guy and had even begun calling him “dad.” By the time the plan was revealed, Foley had no idea what happened, and the newly formed Corporation put the boots to him.
2 Kiss My Ass Club
The most infamous fraternity in all of WWE began the day after the 2001 Survivor Series. Instead of getting fired, the former WCW Commissioner William Regal decided that he would rather denigrate himself and smooch Vince’s derriere than get canned.
From there, Vince didn’t get any more voluntary members, but several superstars were forced into joining the Kiss My Ass Club. Eventually, like most of these other entries – Vince would get his comeuppance and be forced to join his own club. The Rock mashed the Boss’ head into Rikishi’s backside.
1 Degraded Trish Stratus
When you’re the boss of the WWE, you can take as many liberties as you’d like, apparently. McMahon did exactly what a lot of fans would have liked to do and just started to make out all over the arenas with Trish Stratus. While she seemed to have been into it, it also led to what might be all time worst scene in WWE history. The Chairman berated and humiliated Trish on live TV. After forcing her to strip down to her skivvies, he demanded that she barked like a dog for him. It finally came to a head at WrestleMania X7, when the Canadian cutie turned on Vince and smashed him the in grapefruits.