The Most Questionable Vince McMahon Moments Of All Time

Even after quitting in the midst of a scandal, Vince McMahon has established himself as one of the most important people in the history of pro wrestling. He didn't simply change the business, he revolutionized it, taking it to places that no one could have imagined. In that time, he not only survived the changing landscape of sports entertainment but also the onslaught from the likes of WCW and ECW in the late '90s. McMahon didn't just beat his competitors out of business, he bought and dismantled them, proving there's no chance in hell that anyone would topple the empire of the WWE under his watch.

While there's no disputing his undeniable impact on the business, he has been involved in some of the more controversial moments in wrestling as well. Whether it be his involvement in the heated Montreal Screwjob or the serious allegations of misconduct and hush payments (via The Wall Street Journal), McMahon's name can't seem to stay out of the headlines for the worst kind of reasons. Without further ado, let's take a look at some of the most questionable Vince McMahon moments of all time.

In 1997, the landscape of the WWE was different to what it is now. Known then as the WWF, it struggled in the Monday Night Wars against WCW, and it wasn't in the position to offer mega-money deals to its top stars. A year earlier, Bret "The Hitman" Hart had signed a 20-year deal with the company (via Essentially Sports); however, McMahon informed the Excellence of Execution he wasn't able to honor it due to the financial difficulties of the company. As a result, Hart began talks with WCW about a possible move, which eventually came to fruition. There was one problem, though: Hart was the WWF Champion at the time, and due to his real-life feud with "The Heartbreak Kid" Shawn Michaels, he didn't want to drop the title to HBK in front of the Montreal crowd at the 1997 Survivor Series.

So the planned finish was for D-Generation X to run in and create a DQ finish for the bout between Hart and Michaels, and the title issue would have been solved later on. During the match, Michaels put Hart in the Sharpshooter, and McMahon immediately called for referee Earl Hebner to ring the bell, indicating Hart had submitted. The fans in attendance couldn't believe the betrayal that had taken place and neither could Hart, who punched out McMahon backstage. To make matters worse, McMahon conducted an interview after the event, saying "Bret screwed Bret," proving he held absolutely no remorse about how this unfolded.

After the Montreal Screwjob and the real-life disdain fans had towards Vince McMahon because of it, he decided to capitalize on the heat and created the Mr. McMahon character for television. As the ruthless and maniacal owner of the WWE, McMahon was the villain everyone wanted to see stunned by "Stone Cold" Steve Austin. He became one of the hottest heels around and inserted himself in major storylines.

Leading up to WrestleMania X-Seven, McMahon embroiled himself in a narrative arc where he and his wife, Linda, were splitting up, and he began a relationship with Trish Stratus. In a bid to humiliate Stratus and prove that he could do anything he wants, McMahon had Stratus walk around on all fours and bark like a dog in the middle of the ring, before demanding that she strip down on live television. It was a humiliating event for Stratus, especially considering how she is widely regarded as one of the best women's wrestlers of all time and this felt like an angle that could have been avoided entirely. 

Even so, in an interview at For the Love of Wrestling in 2022, Stratus declared she actually loved the angle. "Vince pitched the angle to me like this, 'So we're going to have this angle where you are barking like a dog and get really humiliated, and basically hit rock bottom.' And I was like, 'amazing!'" Stratus said.

There's no doubt that the WWE has pushed the limits of decency and what it can get away with throughout the years — especially in the Attitude and Ruthless Aggression eras. It's central to the old-school mentality that controversy creates cash. That said, there was one shameful moment in the past which should have been avoided entirely, since it was not only done in poor taste, but it was also extremely racist.

In a backstage segment at Survivor Series 2005, Vince McMahon approached John Cena and dropped the N-word casually in conversation, within an earshot of both Booker T and Sharmell. The angle was defended by the WWE, who told TMZ that "[it] was an outlandish and satirical skit involving fictional characters, similar to that of many scripted television shows and movies," but Peacock wasn't interested in having that sort of content on its platform. As per The Hollywood Reporter, the streaming service rightfully took the decision to remove this moment — and other questionable ones — from its acquired WWE library.

The bitter feud between CM Punk and the WWE has been well documented. After feeling burnt out and tired from all the backstage politics, the Straight Edge Superstar walked out of the WWE in January 2014, and the company eventually future endeavored him later that year. However, the nature of how his termination unfolded left Punk furious and seeking legal advice. Appearing on Colt Cabana's "Art of Wrestling" podcast, Punk revealed he had exchanged text messages with Triple H, telling him they would be able to have a proper chat after he returned from his honeymoon. "He did not respond to the text," Punk explained. "The day of my wedding, I got a FedEx in the mail. It was my termination papers. I was fired."

In a sit-down chat with "Stone Cold" Steve Austin (via Cageside Seats), Vince McMahon denied this act was done intentionally. "Sometimes in a big corporation, the legal people don't necessarily know what talent relations are doing and conversely," he said. "Punk got his severance papers moreover on the day he got married. That was coincidence. So I want to personally apologize for that." Punk rejected this apology on a subsequent edition of Cabana's podcast, noting (per The Washington Post) that the package was shipped overnight, and adding "If the apology was sincere, you wouldn't use it as a publicity stunt on Austin's podcast."

Wrestling often blurs the line between reality and fiction. As a matter of fact, it isn't unusual to see events from the real world spill over into the storylines on screen. Yet, there is still tact and timing to everything. In the case of Vince McMahon and the WWE, ratings trump over those two considerations every single time.

At the Badd Blood PPV, Brian Pillman was meant to wrestle Dude Love. However, Pillman passed away in his hotel room before the event. The next night on "Raw," the WWE decided to pay tribute to the wrestler; however, there was a segment that raised eyebrows. McMahon decided to interview Pillman's widow, Melanie, live on air. It was clear that the woman was grieving and still in shock about what had happened a day before, being in no state to discuss the incident so soon after her husband's passing. The wrestling world was left disgusted by the WWE and McMahon's actions that night, which were nothing short of callous and cold towards the Pillman family.

Considering all the dastardly things that Vince McMahon has done to his family as the Mr. McMahon character, it should come as no surprise that there were riskier ideas that never even made it onto the air. One of the more puzzling and head-scratching suggestions was how he wanted to inject his son, Shane, into his daughter Stephanie's real-life pregnancy as an angle on television. There were even rumors that McMahon considered himself as a possible candidate to be revealed as the father of her child, too.

Discussing the incest storyline on the "Opie Radio" podcast, Bruce Pritchard revealed how the concept came about and that he was the one who shut down the idea before it gained any further traction. "It was during the time when Stephanie was pregnant and Vince was trying to figure out if he could work that into a storyline," he said. "It was an entire Sunday, an entire day of my life that I will never get back." The fact this conversation was entertained for as long as it was is concerning, to say the least. More importantly, what did Triple H, the real father, think about all of this?

Allegations against Vince McMahon and how he treats female employees have been around for decades. Many people point to how it was right in front of us that he degraded or treated the WWE's female talent as if they were sexual objects for entertainment. A fictional story broadcast on television — even if it is in extremely poor taste — is no conclusive proof of any wrongdoing; however, McMahon didn't do himself any favors by interjecting himself into these types of spicy storylines and angles.

One of his more controversial moments occurred when he received a dance from Stacy Keibler on a 2002 episode of "SmackDown." McMahon sought out a new assistant and Keibler did her best to convince him she'd be the right person for the job through her seductive dancing. Many memes have come out of this segment, especially in terms of McMahon's facial reactions. However, considering the allegations of how certain employees were promoted within the WWE, this segment is not a good look for him in hindsight.

There's been an ongoing debate about the quality of WWE programming for several years now. A large group of fans — both past and present — believe the lack of new superstars and the endless recycling of storylines have harmed the product. NXT, under the leadership of Triple H, was a breath of fresh air. Focusing on new superstars and delivering high caliber matches and angles, it became one of the most critically acclaimed parts of WWE.

In 2021, Triple H suffered a health scare and had to relinquish his oversight of the brand, as he recovered at home. In this time, "NXT" was overhauled by Vince McMahon and repackaged as "NXT 2.0." Now, this wasn't merely a slight tweak or modification of the presentation, but an entire overhaul of the programming, including wrestlers and even the colors of the brand's graphics. As per Wrestling Headlines, the staff hired by Triple H were all in the crosshairs of the powers that be, and future endeavored in due course. Plus, the whole spot where Bron Breakker smashed through the gold X at New Year's Evil was about as subtle as one of the Cerebral Assassin's infamous sledgehammer shots. (That said, former NXT video producer Cornell Gunter told "The A Show on RNC Radio" podcast (via POST Wrestling) that McMahon called a meeting with the staff before the rebrand and insisted it had been something that he and Triple H had discussed beforehand.)

At the 1999 Over the Edge PPV, the Godfather was scheduled to defend his Intercontinental Title against the Blue Blazer, aka Owen Hart. For Hart's intro, he was meant to descend from the rafters into the ring. However, a tragedy took place when the safety harness failed and Hart plummeted into the ring. It was clear this was an unplanned incident and something had gone drastically wrong. Hart was rushed to the hospital, but he was declared dead on arrival.

After such a traumatizing event, not only for the people in attendance but also Hart's family and friends backstage, the show carried on — minus the bout between the Godfather and Hart. What made matters even worse is that Jim Ross announced the passing of Hart to the audience watching at home, leaving many gobsmacked about why the PPV was still on the air. The decision to continue Over the Edge after Hart's death still draws the ire of many people, since it appeared like Vince McMahon and the WWE chose to pursue a business-as-usual approach rather than treat the event for the heartbreaking tragedy it was.

Legendary wrestling commentator Jim Ross has Bell's palsy, which can cause his facial muscles to paralyze for a short period of time. The wrestling world has been aware of it and supported him as he has battled it and other medical conditions throughout the years. No matter the challenge that he has faced, JR remains one of the most iconic and knowledgeable voices in all of pro wrestling history.

In a 2012 segment on "Raw SuperShow," Vince McMahon crossed the line as he pulled his face and made light of JR's Bell's palsy in an attempt to impersonate the commentator. It was an unnecessary and harrowing moment since there was absolutely no need for McMahon to do it, yet he still chose to. Many figures from the wrestling community weren't impressed with McMahon's sick and cruel attempt at a joke and rightfully blasted him on social media.

During the pandemic, the WWE took the unpopular decision to release a plethora of talent, including the likes of Zack Ryder, Karl Anderson, Luke Gallows, and Rusev (via Sports Illustrated). It was a brutal and widely condemned move by the industry, especially since the company wasn't exactly in dire financial straits but left many wrestlers without the option to find any work in a time when the world had been shut down. The ruthlessness didn't stop there, as the WWE lay off more workers in 2021 weeks before the festive season. Nothing says happy holidays quite like a text message saying "you're fired," right?

Again, Vince McMahon couldn't resist the opportunity of using this to get his character over on television. During a segment with the superstar Theory on "Raw," he gloated about how it warmed him up to fire people over the holiday season. It wasn't exactly embraced as him doing his best Ebenezer Scrooge impression, but rather as him having the compassionate nature of a mango. It was way too soon to joke about something like this.

Think about some of the greatest wrestlers to have never held the WWE Championship. Names like Sting, Roddy Piper, Scott Hall, and Owen Hart immediately jump out. Now, remember that Vince McMahon is both a former WWF and ECW Champion, and none of these performers reached the summit in the company. Sure, one can argue that the predetermined nature of wrestling could result in anyone being elevated to the position of champ, but this is the very definition of going into business for oneself.

McMahon didn't need to hold a title to solidify his evil character at any point. He was the boss and called the shots. In effect, he was always more powerful than any person who held the world championship, since he could simply snap his fingers like Thanos and remove the title from around their waist. Unfortunately, these reigns appeared more like they were catering to someone's vanity and ego rather than providing compelling storytelling.