The life and career of Vince McMahon made him one of the most fascinating public figures ever. McMahon took WWE from a relatively small local promotion that only thrived in New York into a global brand juggernaut. WWE is now a household brand and people often think of the letters WWE before saying the words professional wrestling. McMahon took a lot of creative and personal risks to bring WWE to the mainstream world. There has been a mix of positive and negative stories attached to McMahon with a debate often taking place regarding how he should be remembered when he does retire.

McMahon has done a lot of shady and controversial things on WWE television and in his real life. It skews his perception as being a creative genius and intelligent businessman with negatives being associated with him. Some people view him as a con man that has found a way to hurt the wrestling industry altogether by making it impossible for other promotions to compete on a national or global level. Regardless, McMahon has a lot of things to his name that the average person would regret. We’re going to take a glimpse into his mind and how he views these things today. Here are eight decisions that Vince McMahon regrets and seven that he would do again.

15. Regret: The Undertaker Losing His WrestleMania Streak to Brock Lesnar

via thesun.co.uk

Vince McMahon has never admitted showing any regret for having The Undertaker’s undefeated WrestleMania streak end at the hands of Brock Lesnar, but the writing is on the wall regarding this decision. Lesnar had a lackluster WWE World Championship reign shortly after defeating Undertaker and his first clean loss came at the hands of a 50-year-old Goldberg.

Nothing great directly came from Undertaker losing to Lesnar. We witnessed the final match of Undertaker last year when he lost to Roman Reigns for his second ever WrestleMania defeat. This moment could have meant so much more for what McMahon wants if Reigns ended the streak. We have reached the point where fans will boo Reigns no matter what. The streak ending to Brock rather than Roman is definitely something Vince would change today.

14. Would do again: Pushing Roman Reigns To The Moon So Early

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Roman Reigns winning the 2015 Royal Rumble was met with arguably the biggest backlash from fans. Philadelphia booed him out of the venue and people complained online. Reigns would end up losing out on his planned title win by Seth Rollins cashing in during the Reigns vs. Brock Lesnar WrestleMania 31 main event. Many pundits wonder if Roman would have been better off in the long run not winning this year.

Vince McMahon has believed in Reigns as much as any other wrestler in WWE history based off the way he has pushed him. The following two years would see Reigns win the main events of WrestleMania defeating Triple H and The Undertaker, and he is expected to win it next year by defeating Lesnar. McMahon clearly doesn’t feel any negative feedback or perception towards Reigns is noteworthy enough to slow down his push.

13. Regret: Lex Luger Being Pushed as Hulk Hogan’s Replacement

via wwe.com

One of the biggest failures to come directly from Vince McMahon’s mind was the push of Lex Luger as a main eventer. Luger was an established star from WCW, but the WWE fans failed to welcome him in similar fashion. McMahon wanted Luger to be the official replacement to Hulk Hogan when Hogan chose to leave WWE.

Luger received a patriotic gimmick similar to Hogan and even bodyslammed big man Yokozuna similar to when Hogan slammed Andre the Giant. WrestleMania X was meant to be the crowning moment of Luger, but fans just refused to buy into him as the top star. Bret Hart had more fan support and respect from the locker room. McMahon chose to quit on his elaborate Luger push and made Bret the champ. All of the time and money invested into pushing Luger was a massive waste of money.

12. Would Do Again: Beating “God” In A Wrestling Match

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Vince McMahon is known for having one of the biggest egos not only in wrestling but in all of business. An example of this took place during his feud with Shawn Michaels in 2006. Following their WrestleMania 22 match, Vince and Shane continued going after Michaels and started using his religion as an aspect of the feud.

A tag team match would have both members of the McMahon family facing Michaels and “God” in a wrestling match. “God” did not appear and the McMahon family won the match. Vince started bragging about beating God in a wrestling match and being above the almighty. This perfectly showcased how ridiculous McMahon’s ego would get as he even claimed to be better than God to upset those that believe in a higher power.

11. Regret: Losing CM Punk

via sportskeeda.com

The departure of CM Punk from WWE is still a huge topic that wrestling fans can’t get over. Punk was the biggest star outside of John Cena for WWE in recent years. An unhappy relationship with WWE and Punk led to him making the decision to walk out after the 2014 Royal Rumble match. Punk felt disrespected by Triple H and lied to by McMahon when it came to his career plans.

McMahon reportedly had a good relationship with Punk. Unlike Daniel Bryan who needed to go above and beyond to prove it to Vince, Punk was someone McMahon always had high hopes for. The Stone Cold Podcast with McMahon saw him express regret over how things went with Punk. McMahon would definitely love to bring Punk back for one more run while he is still running things to correct the wrong.

10. Would Do Again: Faking His Own Death

via youtube.com

Vince McMahon apparently had huge plans for WWE when he ran the storyline that saw him “die” on-screen. The limousine of McMahon exploded and the website reported that McMahon was dead. Media platforms actually started picking up the story. This was supposed to be a long term storyline with a big reveal at the end, but a real tragedy ended it.

Chris Benoit murdering his family and committing suicide forced McMahon to end his fake death and try to keep the company afloat during the controversial time period for wrestling. McMahon clearly believes in his visions and likely always wanted to run this story to get the real ending. The ship has sailed but Vince would have loved to get the fake death storyline an ending.

9. Regret: Degrading Trish Stratus In The Ring

via onlineworldofwrestling.com

An all-time low moment used against WWE in various platforms is the segment where Vince McMahon publicly degraded Trish Stratus in front of the crowd on national television. McMahon made Stratus strips to her bra and panties while crawling in the ring on her knees. At one point, Trish was even forced to bark like a dog. It was a horrible idea that still haunts WWE today.

This was used against Linda McMahon during her failed runs for Senate. It is still referenced as to why many people refuse to give WWE a chance due to McMahon being the man behind it. WWE is now trying to market the ladies as credible athletes equal to the men. This footage existing is still a negative skeleton in the closet of WWE that will hurt them.

8. Would Do Again: Daniel Bryan Main Eventing WrestleMania XXX

via bleacherreport.net

There are many beliefs over how Vince McMahon feels about Daniel Bryan’s career after WrestleMania XXX. Bryan was the most popular man in the company, but WWE refused to push him until the fans hijacked the shows with chants. Batista and Randy Orton were going to get slaughtered by the crowd forcing McMahon to give Bryan the moment of winning the WWE World Championship at WrestleMania XXX.

Bryan was forced to relinquish the title shortly after due to injury and would never be healthy for more than a few months. However, the WrestleMania moment established him as a legend in WWE. Bryan is now an extremely important member of Smackdown Live as the General Manager. Despite not wrestling, Bryan gets the biggest pop every week. WWE has value from Bryan for the rest of his career without having to wrestle to add to the show.

7. Regret: Brawl For All

via bleacherreport.net

WWE’s concept of the Brawl for All is another idea that is considered an all-time dumb one from Vince McMahon. The idea of having the wrestlers with boxing or fighting backgrounds would pit them in an unscripted tournament. Everyone in the booking meetings felt Dr. Death Steve Williams would easily destroy the competition and they could push him as a top heel following this.

Instead, Williams was upset by Bart Gunn who eventually went on to win the entire tournament. WWE never got much use out of Williams after this and Bart was one of the least important members of the roster meaning his win was pointless. Many of the Brawl for All competitors suffered injuries as well to add to the bad news. This is an easy regret for McMahon and everyone involved.

6. Would Do Again: Admitting to Cheating on His Wife

via pintrest.com

Vince McMahon showed zero remorse when admitting that he frequently cheated on his wife. This interview took place towards the early 2000s when McMahon would find his way in storylines that saw him making out with the likes of Trish Stratus, Torrie Wilson and Sable. There were always rumors of Vince hooking up with the female talent through the years.

McMahon never revealed if he did anything with WWE employees, but he stated he cheated on his wife Linda McMahon many times. Linda may have already known about this. That didn’t stop it from making her look bad. Vince however likely loved the world knowing that he was with many women in this time frame. At the end of the day, he repaid Linda by buying her way into a position in Donald Trump’s cabinet.

5. Regret: Saying The n-word in Backstage Skit With Booker T

via allwrestlingsuperstars.com

A highly controversial moment from Vince McMahon on screen saw him get involved in a segment with John Cena and Booker T. McMahon tried to comically use the n-word for comedic purposes when talking in hip hop slang to Cena. This skit ended with Vince saying the n-word as he walked past Booker T and Sharmell. McMahon walking passed two black performers after saying it made the segment even worse.

It has lived on as one of the more shameful acts by McMahon on screen. Given how society has changed through the years, this could have delivered damage to the WWE brand if it happened more recently. The story was forgotten after a few months in 2006, but it still gets brought up when someone has an argument against WWE for their problematic moments.

4. Would Do Again: Katie Vick Insanity

via monstersandcritics.com

Bruce Prichard recently shared some of the inside scoops from behind the scenes of the Katie Vick angle. Vince McMahon wanted Triple H to dress like Kane and pretend to hump a dead body inside of a casket meant to be Kane’s dead ex-girlfriend. This over the top segment is still regarded today as one of the worst stories in wrestling history.

Both Triple H and Prichard were adamant against Vince’s wishes. All parties reached an agreement where they would film two versions with both visions. Once McMahon filmed the one he wanted, he changed his mind and decided they wouldn’t film another. This was the segment we saw on television that is still ridiculed today. Prichard revealed McMahon loved it and was very proud of what they did. The insane mind of Vince clearly wouldn’t change this despite history saying it should be regretted.

3. Regret: Starting The XFL

via the-void.co.uk

A non-wrestling move that showcased Vince McMahon’s ego in the worst of ways was the XFL. McMahon partnered with Dick Ebersol at NBC. This was during the hottest period in WWE history during the Attitude Era. McMahon believed his version of football with more violence, vulgarity and sex appeal would be a viable competitor to the NFL.

Instead of becoming an instant ratings threat to the NFL as Vince expected, it was one of the most colossal failures in television history. Fans tuned out in droves and critics trashed it for appealing to the lowest form of entertainment. The XFL only lasted one season and is considered McMahon’s biggest failure. WWE and NBC lost $35 million proving McMahon’s vision was not bulletproof as he thought.

2. Would Do Again: The Montreal Screwjob

via sportskeeda.com

Vince McMahon’s most controversial decision in WWE definitely was the Montreal Screwjob. It was the only confirmed instance of McMahon flat out lying to a wrestler about what was going to happen in the ring. Bret Hart was shocked when the referee called for the bell and declared the match over when he was in Shawn Michaels’ version of the Sharpshooter.

The Montreal Screwjob has been discussed and debated by fans, experts, wrestlers and the people that were involved in it for the past twenty years. McMahon regrets things going so poorly to end Hart’s legendary WWE career. However, he has never expressed any inkling that he wanted another result on the night of Survivor Series 1997. It actually did help set up a lot of variables in place that worked out for WWE.

1. Regret: Owen Hart’s Stunt And Continuing The Show

via washingtonpost.com

The biggest regret for Vince McMahon and many people in WWE involves the worst case scenario for a relatively pointless decision. McMahon along with Vince Russo and others wanted Owen Hart to repel to the ring from the rafters for an entrance as the Blue Blazer. This was for a lower card match and an extremely small percentage of fans would have even remembered this if it worked.

Unfortunately, the pointless risk gave us the most heartbreaking moment in WWE history when Hart fell from the rafters to the ringside area instantly dying. WWE announced the death shortly after it happened but continued to go through with the rest of the show. Fans and talent were heartbroken as everyone else performed. If Vince could take one thing back in his life and career, it would definitely be Owen’s entrance stunt that killed him.

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