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5 Most Complicated Vince McMahon – Wrestling Relationships

Vince McMahon had some interesting relationships with some of his wrestlers. So, here are the 5 most complicated the WWE chairman ever had.

Vince McMahon had some interesting relationships with his WWE wrestlers in the past, but which were the 5 most complicated? Here is the lineup of Vince McMahon’s 5 most complicated wrestling relationships!

Vince McMahon and Bruno Sammartino

Vince McMahon and Bruno Sammartino - 5 Most Complicated Wrestling Relationships

The relationship between Vince McMahon and Bruno Sammartino tops our list of 5 most complicated wrestling relationships. But what started the odd relationship between Vince McMahon and Bruno Sammartino?

Well, it all boils down to Bruno’s retirement interviews. In 1987, Sammartino retired for the second time. 

After his retirement, Bruno Sammartino mentioned to several journalists that he did not like the direction of the WWE under Vince McMahon. Evidently, this caused some hard feeling withs the WWE chairman.

It appears the problems between Vince McMahon and Bruno Sammartino did not start after his retirement. In fact, Sammartino recalled how many WWE superstars at the time were involved in drugs and steroids.

Between 1984 and 1987, Sammartino refused to travel with other WWE superstars due to their alleged drug use. He also refused to be inducted in the Hall of Fame after retirement.

Things eventually changed thanks to Triple in 2013. HHH repaired the relationship between McMahon and Sammartino, leading to his Hall of Fame induction that same year.

Vince McMahon and Stone Cold Steve Austin

Vince McMahon and Stone Cold Steve Austin

Stone Cold Steve Austin and Vince McMahon have been feuding on our screens for years. However, Steve Austin and Vince McMahon actually feuded behind the scenes too.

The relationship between Vince and Stone Cold was mainly good. However, things changed in June 2002. It all came to ahead when Vince McMahon asked Steve Austin to lose to Brock Lesnar.

Interestingly, Stone Cold had no problems losing to Brock Lesnar. However, he wanted the match to get a proper buildup. 

When the request felt on deaf ears, Stone Cold promptly left the WWE and did not show up to Raw. Stone Cold and Vince McMahon did not talk for a full six months.

Steve Austin would eventually patch things up with Vince McMahon. However, if not for Jim Ross, the pair might still be arguing today. 

Later on, Steve Austin revealed that Vince McMahon actually fined him $650,000. In the end, Vince McMahon reduced the amount to $250,000.

Vince McMahon and Bret Hart

Vince McMahon and Bret Hart

Out of our entire list of 5 most complicated wrestling relationships, this is probably the most complicated one. 

Most people are quite familiar with the strange relationship between Vince McMahon and Bret Hart. Vince and Bret knew each other for a long time, but their strange saga did not truly being until the Montreal Screwjob.

At Survivor Series 1997, Vince McMahon changed the winner of the match behind the scenes. It led to Hart being set up and losing the title to Shawn Michaels. 

Because of the event, Bret Hart spit in the face of Vince McMahon on live television. He also knocked him out cold backstage.

After suffering a stroke in 2002, Bret Hart eventually made his peace with Vince McMahon. Nevertheless, their relationship never went fully back to what it was.

Vince McMahon and The Ultimate Warrior

Another addition to our list of 5 most complicated wrestling relationships is the relationship between Vince McMahon and The Ultimate Warrior

The Ultimate Warrior and Vince got along fine for most of the eighties and early nineties. However, things changed dramatically in 1991.

Shortly before Summerslam 1991, Ultimate Warrior sent a letter to Vince McMahon with some financial demands. If they were not met, Warrior would not show up at Summerslam.

Vince McMahon met the demands of Warrior, but suspended him from WWE shortly after Summerslam. The Ultimate Warrior would make a return in 1992 and 1996, but only briefly.

To make matters worse, WWE released a rather unflattering DVD about Ultimate Warrior in 2005. Throughout the DVD, former WWE colleagues made a lot of negative remarks about Warrior. 

The DVD certainly did not help the relationship between Vince McMahon and Ultimate Warrior. But things would change again in 2014.

In 2014, The Ultimate Warrior reconciled with Vince McMahon and he was inducted into the Hall of Fame. Disaster struck shortly after the induction though, as Ultimate Warrior died of a heart attack three days after the ceremony. 

WWE would eventually reveal “The Warrior Award”. The award has been given to someone who exhibited unwavering strength and perseverance and is usually given by The Ultimate Warrior’s wife.

Given everything that happened between McMahon and Ultimate Warrior, the award truly came as a surprise. 

Vince McMahon and Jeff Jarrett

5 complicated wrestling relationships

Our list of 5 most complicated wrestling relationships ends with Vince McMahon and Jeff Jarrett. Obviously, there is a lot of history between these two men.

The problems between Vince McMahon and Jeff Jarrett started at the No Mercy pay-per-view of 1999. Interestingly, the problems were similar to those of Bret Hart, more specifically Jarrett leaving the WWE around the time of a major title match.

Jeff Jarrett’s contract was over a day before the No Mercy pay-per-view. To appear during the event, Jarrett had to negotiate a deal with Vince. 

As the story goes, Jeff Jarrett took some liberties when it came to the contract negotiations. It is believed Jarrett held Vince McMahon to ransom for the tidy sum of $300,000.

When the pay-per-view eventually took place, Jarrett lost to Chyna, who was crowned as the new champion. While it was a milestone moment for women’s wrestling, it was a serious downward spiral for Jarrett.

In March 2001, Vince McMahon proved there was a lot of bad blood between him and Jarrett. In fact, the chairman said the following after he took over WCW.

“As far as the Jeff Jarrett’s of the world are concerned, you know how Jeff spells his name: that’s J-E, double F. Well, you know what? I would suspect that we spell it a different way after tonight. That would be capital G, double O, double N, double E. Gone.”

Once Jarrett left the then defunkt WCW, he spent a lot of time on the indies. He eventually decided to start his own wrestling promotion Global Force Wrestling (but that is a story for another time).

It took many years for Jeff Jarrett and Vince McMahon to make amends. In fact, he was only inducted into the Hall of Fame in 2018. 

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