The success of Vince McMahon is unquestioned with the powerhouse of WWE speaking for itself. McMahon’s vision and risk taking led WWE to enter the mainstream increasing the popularity of wrestling. The inception of WrestleMania ushered in a new era many pundits didn’t believe would ever work. McMahon continued the magic over the years and WWE is now a global phenomenon. Fans all over the world enjoy the WWE product and WrestleMania is now as big as any major annual event aside from the Super Bowl. McMahon will be remembered for his successes, but he has been involved in quite a bit of failures in his time.
It would be a bold faced lie if Vince claimed he had no regrets throughout his career. The top position means everything starts and stops with McMahon’s decision making. A desire to branch out into other business and entertainment fields has hurt the reputation of McMahon outside of wrestling. The negative feedback of wrestling fans has also seen many wrestling fans react poorly to his ideas. McMahon clearly doesn’t like to admit he's wrong but sometimes the writing is on the wall. We'll look at fifteen of the worst moments that led to Vince McMahon regretting his decision.
15 Pushing Roman Reigns Too Early
It's blatantly obvious that Vince McMahon desperately wants Roman Reigns to succeed John Cena as the face of WWE. Fans have reacted negatively partly due to McMahon’s love of Reigns forcing him down their throats. The sad part is that Roman was actually a huge fan favorite with The Shield before the group split and WWE tried making him the new chosen one.
Reigns was booed out of the building on his big night at the 2015 Royal Rumble when he won the match in front of one of the most hostile crowds in WWE history. WWE changed plans by having Seth Rollins cash in his Money in the Bank title shot to get out of having Reigns winning the WWE Championship at WrestleMania 31. McMahon changing the plans proved he regretted the early push of Roman. That is no longer the case with WWE doubling down of having Reigns defeat The Undertaker in the legend’s final match.
14 Trying To Have Lex Luger Replace Hulk Hogan
Another past instance of Vince McMahon regretting his choice of making someone the face of WWE was Lex Luger’s push. WWE gave Luger a patriotic character and monster push as a face following the departure of Hulk Hogan in 1993. McMahon believed anyone with the impressive physique and love of the country would translate to major money coming in.
Fans reacted poorly to Luger and he failed as a top star. WrestleMania X plans were originally supposed to feature Luger defeating Yokozuna to get his crowning moment as the WWE Champion. McMahon officially quit on Luger’s push after regretting it and instead went with Bret Hart. The win made Bret the face of WWE for a couple of years and Luger left WWE shortly after.
13 Saying The "N Word" During Backstage Segment
The popularity of the internet has allowed controversial moments to stand the test of time. You can find almost anything that happened on WWE television via a video website today. One of the more shameful moments revolves around a poor decision by Vince McMahon. A backstage segment at Survivor Series 2005 saw him become part of a comedic segment with Booker T and John Cena.
The character of Cena still revolved around the hip hop persona that had him often use popular slang. McMahon tried to “fit in” with Cena by reciting rap slang including using the n-word before turning around and walking passed Booker T. It was meant to be a laughing matter but many called him out on it back then. Today, the segment is clearly not acceptable and something McMahon has to regret considering the desire to continue growing WWE as a global brand.
12 The Brawl for All
Vince McMahon thinking outside the box with innovative ideas often leads to success. One that went the complete opposite direction was the Brawl for All. Instead of the scripted entertainment in the ring, WWE held a tournament with wrestlers competing in real fights. The stars on the roster that had experience in boxing, MMA or other forms of fighting battled it for the prize of $100,000.
McMahon’s plan with the Brawl for All was to have new talent Dr. Death Steve Williams use his wrestling background to destroy the competition. Williams was to move on to a feud with Steve Austin for the WWE Championship. Instead, Williams was knocked out, suffered an injury and lost his push. The irrelevant Bart Gunn won the whole thing. Between the actual goals flopping and many injuries coming from it, McMahon obviously made an enormous mistake.
11 Pitching Incest Storyline With Stephanie
The ideas of Vince McMahon luckily don’t always win out. WWE did a documentary DVD about McMahon that featured many of his peers and loved ones speaking about his pitches. Stephanie McMahon revealed one of the more creepy ideas her father ever thought of. During Stephanie’s real life pregnancy, Vince wanted to have a storyline about it that would have seen him be the father.
Vince wanted to feud with Triple H over Stephanie’s baby with an incest storyline. Stephanie thankfully shut down any potential of this playing out on television. Still, the fact that this idea even surfaced in wrestling circles is one of the more embarrassing stories associated with Vince. You have to believe he regrets ever bringing it up and the aftermath of it proving an insight into his odd way of thinking.
10 Coming Out For The 2005 Royal Rumble Match
The finish of the 2005 Royal Rumble match featured John Cena and Batista both eliminating each other at the same time. Vince McMahon walked to the ring with the power strut associated to him. The walk was extra intense this time around and made for a horrible moment in his life. McMahon slipped walking into the ring to cut his promo and tore both of his quads.
Unable to stand, McMahon sat on the mat in pain before demanding the match get restarted. Vince is a very prideful man that hates to look bad on television unless it's meant to make one of the wrestlers look good in the process. This was just a humiliating and painful moment for him that still manages to get lots of views online. WWE could have just had the referees restart the match to save McMahon the pain.
9 Letting Shane McMahon Leave WWE
The love Vince McMahon holds for his children made it a tough decision to figure out who should succeed him. Stephanie McMahon and Triple H ending up winning out and are working alongside Vince before taking over. It left Shane McMahon out of the loop after believing he would at least have a say in the future of the company.
Vince’s decision created the chain of events that had Shane leave WWE to find his own path with business ventures in other countries. It's rumored that Vince regretted Shane leaving the family business for many years before finally returning in 2016. Shane becoming a full-time part of WWE television filled Vince with happiness to see his son back in the fold of the industry he loves. Sadly for Shane, he's still significantly below Stephanie in the pecking order.
8 Having Hulk Hogan Win The Title At WrestleMania IX
A horrible wrestling decision made by Vince McMahon came at the end of WrestleMania IX. Bret Hart and Yokozuna faced off in the main event for WWE Championship. Instead of anointing Hart as the face of the company or going all the way with Yokozuna as a monster heel, McMahon decided to ride the bandwagon of Hulk Hogan once again.
Fans were tired of Hogan with the Hulkamania character dominating WWE for over a decade at that point. Hogan eventually decided to leave WWE a few months later making his title win completely pointless. McMahon wanted Hogan to pass the torch by losing to Hart before leaving, but Hogan refused to make the decision even worse. 1993 is one of the worst years in WWE history with this decision setting the tone for a disappointing time.
7 World Bodybuilding Federation
Vince McMahon invested a lot of money and effort into creating the World Bodybuilding Federation back in 1991. McMahon’s love of bodybuilding inspired him to try to compete with the International Federation of Bodybuilding. An attempt to market the bodybuilding competitions similar to wrestling shows with the pageantry and characters did not impress the fan base.
The WBF PPV did atrocious numbers failing to show any signs of potential. McMahon quickly realized it and the bodybuilding promotion would only lose him money. The World Bodybuilding Federation closed their doors faster than anyone would have imagined. It's still viewed as one of the biggest failures attached to the legacy of McMahon. The death of WBF didn’t stop Vince from continuing to push his favorite bodybuilder physiques in WWE.
6 Batista Winning 2014 Royal Rumble
A somewhat recent example of Vince McMahon being out of touch with his audiences took place at the 2014 Royal Rumble. Daniel Bryan was the most popular star in WWE with fans having the hope he would win the Rumble. Instead, WWE went with the returning part-time star Batista. Every WWE show going forward featured fans booing Batista louder than ever and cheering on Bryan with extra passion.
McMahon typically stays the course to avoid showing he was wrong. This incident forced his hand making him admit he regretted his decision by changing the main event of WrestleMania XXX. Bryan was added to the main event and Batista turned heel. It all worked out in the end, but McMahon was horribly off the mark thinking fans would prefer Batista to Bryan. We're all better off for him regretting his decision here.
5 Chris Benoit Tribute Show
The shocking death of Chris Benoit shook the wrestling industry. WWE decided to air a tribute episode showcasing Benoit’s best matches along with touching words from the wrestlers that loved him. It was discovered hours after the episode that the deaths of Benoit and his family were a result his double murder suicide. WWE and Vince McMahon received horrible feedback for airing the tribute to a man that would later be discovered as a murderer of his wife and young son.
It forced McMahon to end his storyline death from the prior week to apologize on air for the Benoit tribute episode. You can’t fault him for this one given the unpredictable nature of this heartbreaking story. However, it still remains one of the biggest regrets of McMahon’s time running the WWE. The Benoit story almost destroyed wrestling but WWE did find a way to rebound from the months of bad publicity.
4 Not Buying UFC
Most of the regrets on this list have come from poor decisions Vince McMahon went through with, but one of his biggest errors came from saying no to an idea. Shane McMahon has always been a huge MMA fan and tried to broker a deal to purchase UFC back in 2000. The correct assessment by Shane knew UFC could be a valuable asset to own and run, but Vince shut down the idea.
Vince allegedly didn’t think a sport as violent as UFC could be marketable or turn into mainstream success. All these years later, UFC is now widely accepted in mainstream sports and arguably more popular than WWE. The McMahon family could be dominating both professional wrestling and Mixed Martial Arts if Vince didn’t make such a bad a decision.
3 Ending WCW After Buying It
The Monday Night Wars created the most success professional has ever witnessed. WWE has failed to match the popularity of the late 90s. Vince McMahon purchasing WCW and ending his competition was among the biggest stories in the history of the industry. Everyone expected the dream storyline of WCW versus WWE to finally come through in a highly anticipated promotion war we’ve wanted for years.
McMahon instead opted to run a four month storyline that featured mostly WWE stars working for both sides before completely ending WCW. The thought process of McMahon was that those that always watched WWE would continue and the WCW viewers would join as well to create new ratings records. Instead, the ratings dropped and many of the diehard WCW fans stopped watching in general. Vince must regret missing out on not utilizing a highly successful brand that fell on his lap.
2 Controversial Trish Stratus Segment
Something that will always haunt Vince McMahon was a segment that paints him poorly both as a promoter and as a talent. McMahon dated Trish Stratus as part of a storyline in 2001 that was bad enough. It reached a new low when McMahon degraded Stratus in the ring on live television. Trish was forced to strip in her underwear and crawl around the ring barking like a dog.
Opponents of Linda McMahon in political races used the footage to disparage the McMahon family name. The footage is still shown any time someone wants to showcase the negative side of Vince as a human being. No matter how much time passes, the visual of McMahon telling Stratus to bark like a dog will always be a historically terrible WWE moment that Vince likely regrets.
1 The XFL
The biggest regret of Vince McMahon’s professional life will always be the failure known as the XFL. WWE reaching new heights with their success during the Attitude Era increased the ego of McMahon. It influenced the decision to start the XFL with the hopes of competing with the NFL. WWE paired with NBC to put a lot of money into the league.
McMahon added sleazy elements of the Attitude Era that football fans didn’t care for. NBC and WWE lost $35 million during the one season of continuous flops. The embarrassing failure made McMahon a laughing stock in the news for his horrible mistake in judgment. It's still referred to as his worst decision to this day. The XFL has a legacy for all the wrong reasons, including being the biggest regret of McMahon that lost him a lot of money.