Vince McMahon has never been afraid of failure. He’s never shied away from making mistakes. He didn’t build the WWE into the huge international phenomenon it has become – one that broadcasts in 150 countries and over 30 languages - by resting on his laurels and maintaining the status quo. Vince McMahon had to take a lot of risks to get where he is as the chairman of wrestling’s top promotion. Many of those risks have paid off, but there have also been many risks that ultimately failed. Vince McMahon will have to live with the consequences of those failures.

Some of Vince McMahon’s failures have been small, like letting a bad gimmick go on for too long or passing on a superstar who would go on to have success elsewhere. Other times his actions, not only in the wrestling industry, but also in other business ventures and even in his personal life had more disastrous results. On a select few occasions, Vince McMahon’s actions even crossed the line.

All of the good and bad decisions Vince McMahon has made make up who he is, but some of his actions are harder for us to forgive than others. CM Punk once criticized Vince McMahon for being a millionaire who should be a billionaire and although he has regained his billionaire status, he could easily lose it again tomorrow with another bad decision. So long as his smart decisions outweigh the poor decisions, Vince probably doesn’t care too much about most of his failures or what anyone else thinks of them. However, that won’t keep his critics from harping on them for the rest of his life and there are a few that even the blusterous billionaire may have a hard time letting go of.

Here are the top 15 things Vince McMahon will never live down.

15 15. The WBF

via customwebproductions.com
via customwebproductions.com

In 1990 Vince McMahon attempted to venture outside of the wrestling industry by creating the World Bodybuilding Federation. The promotion featured stars with large, over the top characters cutting promos during the events, which went against McMahon’s claim that he would keep the world of bodybuilding separate from that of professional wrestling. The sport drew very little interest and received terrible reviews. One event was held in 1991 and another in 1992 - the latter of which had a total of just 3,000 par-per-view buys - before the company ceased operations.

Between the WBF, McMahon’s line of ICOPRO bodybuilding supplements, Bodybuilding Lifestyle Magazine, and the WBF BodyStars television show, McMahon lost a total of $15 million.

14 14. Brawl for All

via wwe.com
via wwe.com

In 1998 the WWE came up with the idea to have a 16-man tournament featuring legitimate fights with 20 ounce gloves, dubbed the Brawl For All. Participation in the bouts was strictly voluntary and Steve “Dr. Death” Williams was picked as the company’s favorite to win, with the idea of setting up a match between Williams and Stone Cold Steve Austin. That plan went awry when Williams was knocked out by Bart Gunn in the tournament’s quarterfinals.

Gunn went on to beat Bradshaw in the final, but the victory did very little to enhance his career and set him up to be embarrassed when he fought Butterbean at WrestleMania XV. The tournament left several wrestlers injured, including Savio Vega who suffered a career ending arm injury, and confused fans who had watched wrestling for its scripted nature. It was far from Vince McMahon’s best moment of the Attitude Era.

13 13. Losing $350 Million in One Day

via wwe.com
via wwe.com

In May of 2014 the WWE reached a new television agreement with NBCUniversal. The deal gave the WWE a 50% raise over their previous deal, but it had been expected that the deal would double or triple the size of the old one. As a result, the company’s share values dropped from $29.12 per share to $19.96 causing Vince McMahon to lose $350 million in a single day.

The initial struggle of the WWE Network to reach their goal of one million subscribers in order to break even, had also hurt his worth and cost him $325 million that April. In March of 2014 McMahon had a net worth of approximately $1.6 billion and within the span of two months it had dropped to $750 million. His worth has since reached the $1 billion mark again, but that one big loss won't soon be forgotten.

12 12. Linda McMahon's Senate Bids

via nytimes.com
via nytimes.com

Linda McMahon campaigned unsuccessfully in 2010 and again in 2012 to become a member of the United States Senate. Her husband’s wrestling background made her an easy target for her opposition who often cited many of the numerous deplorable storylines in the WWE’s history as proof that she was not suited for the position. The WWE attempted to clean up their image by going PG and becoming a more family oriented product, much to the chagrin of long time wrestling fans who viewed it simply as a transparent ploy to garner votes.

In the end, Linda McMahon conceded the loss in 2012 and the McMahon family was out the $97 million of their own money they had spent on her two campaigns.

11 11. The Steroid Scandal

AP Photo/Mark Lennihan
AP Photo/Mark Lennihan

It had long been suspected that professional wrestlers were using performance enhancing drugs and in 1994 the allegations came to a head when Vince McMahon was indicted on charges for illegal distribution of steroids. He temporarily gave up control of the WWE to his wife, Linda, while the case went to trial where Kevin “Nailz” Wacholz testified that McMahon had ordered him to use steroids. Wacholz's credibility was called into question due to his admitted hatred of McMahon.

Hulk Hogan was intended to be the star witness against McMahon, but Hogan testified that McMahon had never told him to take steroids nor did he try to sell them to him. McMahon was acquitted of the charges and went back to running the WWE, but many people wanted nothing to do with a business run by a man who may have been a drug dealer. The result was a $4.431 million loss for the WWE in 1994-95 and many people have never forgiven or forgotten the steroid scandal.

10 10. Ending the Streak

via foxsports.com
via foxsports.com

The Undertaker’s undefeated streak at WrestleMania was one that many people believed would never be broken. It had become his legacy and it was thought that ‘Taker’s career would end without him ever having lost on the “Grandest Stage of Them All”. So when Brock Lesnar ended the streak at WrestleMania XXX, people were shocked and left wondering what purpose it ultimately served. Some felt that the loss tarnished The Undertaker’s legacy while others believed that if the streak was going to be broken, it should’ve happened courtesy of a young, up and coming star in need of a big push, as opposed to one of the most over superstars in the business.

The obvious answer for why Lesnar was given the honor is that it was done to help establish his dominance, but that doesn’t sit well with fans who aren’t about to let Vince McMahon forget about this decision anytime soon.

9 9. His supposed feud with Randy Savage

via sportskeeda.com
via sportskeeda.com

The Macho Man Randy Savage was one of wrestling’s brightest stars, yet he made his last appearance in the WWE in October of 1994 and never stepped foot inside the promotion’s ring ever again. What exactly the reason is, no one aside from Vince McMahon really knows. There have been rumors over the years about why Savage never returned after the downfall of WCW and many insist that there was some sort of long standing feud between the two parties, with it being reported that McMahon couldn't stand the mention of Savage's name.

With Savage’s passing in May of 2011, the chance for a final WWE appearance came to an end. Few fans have forgiven Vince McMahon for not burying the hatchet when he still had the chance.

8 8. Mr. McMahon’s Kiss My Ass Club

via spokeo.com
via spokeo.com

In 2001, Vince McMahon created the “Mr. McMahon Kiss My Ass Club”. In a segment that aired several times until 2008, a WWE superstar or announcer would be called to the ring and ordered to beg to keep their job and to pucker up and smooch McMahon's bare buttocks or risk being “fired”. It was a terrible and disgusting idea that no one outside of McMahon enjoyed. Yet, he thought so highly of the segment that the WWE even created an animated web series based on the idea.

Thankfully, Mr. McMahon's Kiss My Ass Club – The WWE's Most Valuable Asset didn’t last very long and was canceled as part of a settlement between the WWE and Cartoon Network due to its similarities to the latter’s Assy McGee. This idea never would’ve seen the light of day in the current PG-era WWE and the fact that it did is something many will never let Vince McMahon live down.

7 7. His relationship with Donald Trump

via zimbio.com
via zimbio.com

Donald Trump is the most toxic man in America right now. His 2016 Presidential Candidacy is viewed by many as a complete joke and his racist comments and desire to ban all Muslims from the USA has drawn disdain from people across the globe. He’s also a long time friend of Vince McMahon and has made several WWE appearances over the years. At WrestleMania 23, Trump, represented by Bobby Lashley, defeated the WWE chairman, represented by Umaga, in a hair vs. hair match and in 2009 he temporarily “bought” Monday Night Raw.

In 2013 Trump was inducted into the WWE Hall of Fame and recently a petition has been making the rounds to have him removed, but the WWE has yet to act on the matter and it’s likely they won’t. Instead of cutting ties with Donald Trump, Vince McMahon appears willing to go down with the sinking ship by association. That’s going to be difficult for some fans to look past.

6 6. Katie Vick

via wrestlecrap.com
via wrestlecrap.com

The Katie Vick storyline is easily the most disturbing angle in WWE history and many who witnessed it still wonder how it managed to make it to air. During a 2002 feud, Triple H accused Kane of murdering Katie Vick, a woman to whom the Big Red Monster had unrequited love. Triple H then suggested that Kane had either raped Katie Vick while she was alive or engaged in necrophilia. The despicable angle was made worse when Triple H attended Katie Vick’s “funeral” wearing Kane’s mask and re-enacted the alleged ordeal by simulating sexual intercourse with a mannequin. Thankfully, the angle ended a short time later, but not without leaving fans questioning what Vince McMahon was thinking.

5 5. His Treatment of Women

via sportskeeda.com
via sportskeeda.com

Vince McMahon is a self-proclaimed lover of women, yet he’s continuously showed a total lack of respect for the opposite sex. He’s degraded women through various storylines over the years, with the most memorable moment coming when he had Trish Stratus strip down to her underwear and crawl around the ring, barking like a dog.

Unfortunately, McMahon’s exploits of women aren’t just limited to scripted wrestling angles. In 1992, former WWE referee Rita Chatterton went on an episode of Geraldo Rivera’s Now It Can Be Told show and accused McMahon of rape. The McMahons filed a lawsuit against Chatterton, but later dropped it to focus on the steroid trial.

4 4. Owen Hart's Death

via imgur.com
via imgur.com

At the May 23, 1999 Over the Edge pay-per-view, Owen Hart fell 90 feet to his death when the early release mechanism on the harness that was to carry him from the rafters to the ring let go. Afterwards, Vince McMahon made the controversial decision to continue the event. Hart’s family sued the company and won an $18 million lawsuit.

Although it is common knowledge that the stunt was the brainchild of Vince Russo and Hart agreed to it, Bret Hart maintains that had he still been with the WWE, he never would’ve allowed his brother to do it. One of the promotion’s top wrestlers lost his life under Vince McMahon’s leadership and that’s something he’ll have to live with for the rest of his life.

3 3. The Chris Benoit Double Murder/Suicide

via sports-vice.com
via sports-vice.com

In 2007 a segment aired on Monday Night Raw in which Vince McMahon’s limo exploded, supposedly killing the WWE chairman. One week later, the storyline was dropped when the body of long-time superstar Chris Benoit was found along with that of his wife and son. The WWE spent the entire night paying tribute to Benoit. As the night came to a close, details started to come out revealing that Benoit had killed his wife and son before taking his own life and although they couldn’t have known what had transpired, the tribute made the WWE look pretty bad. They were quick to distance themselves from Benoit, removing any mention of him from all past and future programming.

Studies of Benoit's brain revealed that it was equal to that of an 85-year-0ld Alzheimer's patient, due to years of physical abuse. Following the incident, the WWE instituted the imPACT Concussion Management Program and banned chair shots to the head, but it's hard to forgive them for being complicit in Benoit's tragic demise.

2 2. The Montreal Screwjob

via wrestleenigma.com
via wrestleenigma.com

The Montreal Screwjob that took place at the 1997 Survivor Series pay-per-view when Vince McMahon legitimately cost Bret Hart the World Title is the most controversial event in WWE history. Not only did McMahon ask to get out of a recently signed 20-year contract with his biggest star, but he then overruled Hart’s creative control clause in his contract that would keep him from losing the belt in Canada and allow him to depart to WCW on his own terms.

The world of professional wrestling was never the same after that night, several wrestlers quit or threatened to quit the promotion and many people remain strong in their hatred of Vince McMahon for not doing what was right and proving his dishonesty, even if the real outcome was what was best for business.

1 1. The XFL

via bleedphilly.com
via bleedphilly.com

In 2000 Vince McMahon once again ventured outside of the wrestling industry and launched a professional football league. The XFL was a failure and ceased operations in May of 2001 after just one season and $35 million in losses for both the WWE and NBC, the XFL’s broadcaster. The sport was popular among some, but drew a lot of criticism for featuring pep talks from WWE personalities and very poor play-by-play commentary. Perhaps the biggest thing going against the XFL was that Vince’s wrestling background caused many to question the legitimacy of the game's results.

There are many things that Vince McMahon has done in his lifetime that he will never live down, but most of them exist within the realm of professional wrestling. The failure of the XFL extends far outside that realm and provides a point of ridicule for people whose only knowledge of Vince McMahon exists because of the XFL, making it the number one thing he will never live down.