15 Things You Didn't Know About The Undertaker And Vince McMahon's Relationship

Vince McMahon is the greatest wrestling promoter and entrepreneur ever. The world of wrestling has changed for the better ever since he created the WWE. It's the biggest promotion in sports entertainm

Vince McMahon is the greatest wrestling promoter and entrepreneur ever. The world of wrestling has changed for the better ever since he created the WWE. It's the biggest promotion in sports entertainment where millions of fans across the world follow the top wrestlers on the planet.

The Undertaker is arguably the best wrestler to ever live. He's been going strong for nearly 30 years in the WWE, fighting all of the top talents you can think of not named Sting. He and Vince McMahon have had a relationship like no other and remain extremely close to this day.

If you look at the history of Vince McMahon and other wrestlers, you'll see the relationship between them was rocky at best. But when it comes to these two men, it's always been love, kindness, and friendship. The two have simply kept a friendship of extraordinary heights.

Here are 15 surprising facts about the history of their relationship you didn't know about.

15 The Undertaker Confronted him After Montreal Screwjob


Every wrestling fan knows about the Montreal Screwjob, but not all of them know the full details, so we will kindly explain. Vince McMahon had signed Bret Hart to a 20-year deal but wasn't able to afford it. He simply told Hart to go to WCW where he could earn more money. Hart reluctantly agreed. The only thing he asked for was to beat real-life rival Shawn Michaels at Survivor Series in 1997 with the WWE Championship on the line.

The match took place in Montreal (Hart's home country in Canada). The match was scheduled for Hart to win, but Vince had officials ring the bell on a submission maneuver by HBK (though Hart didn't tap).

Hart angrily attacked Vince backstage. Even though this isn't well-known to some, The Undertaker actually confronted Vince. The reports go that he went to McMahon's office and demanded he apologize to Hart. Of course, that didn't happen for many years, but 'Taker willingly stood up to the boss.

14 The Undertaker made J.R. Kiss McMahon's Derriere


Remember that ridiculous "Kiss my Ass Club," storyline Mr. McMahon created, where wrestlers had to show their respect for the boss by kissing his butt in the middle of the ring. This usually involved more comical wrestlers like Rikishi, The Rock and others. But believe it or not, The Undertaker made Jim Ross kiss McMahon's you-know-what.

The Undertaker was part of Team WWE that defeated The Alliance at Survivor Series. after that, The Undertaker turned heel when he forced Jim Ross to go in the middle of the ring and kiss none other than Vince's billion dollar butt.

This began a failed heel turn for 'Taker, who went in a forgetful "Big Evil" gimmick that everybody would love to forget. Including himself.

13 The Undertaker wasn't Happy after WrestleMania 32


WrestleMania 32 was easily one of the more forgettable pay-per-views that the company has ever put on. Shane McMahon and The Undertaker's Hell in a Cell match was lackluster at best, except for Shane O'Mac's jump off the top of the cage.

To make matters worse, The Undertaker wasn't very happy with Mr. McMahon before or after the event. The reports go that McMahon wanted to have his son win, and The Undertaker was bothered by it and refused to lose. After the match, McMahon apparently kept trying to get in touch with The Deadman about his future plans.

The Undertaker wasn't on speaking terms with McMahon and ignored his phone calls. There was even speculation that The Undertaker had wrestled his last match and was bothered by Vince's constant requests for him to come back.

Well, with 'Taker showing up at SmackDown 900, we know that's not the case anymore.

12 Vince Attributes The Undertaker to Helping Beat WCW


From 1996-1998, WCW was destroying WWE in the Monday Night War. Eric Bischoff built the nWo and handed out boatloads of money to Vince's former mega stars. Bischoff assured his company and the wrestling world that WCW would put WWE out of business once and for all.

Vince talked about being in a real tough point of the wars where it looked like WCW would pull away. He talked about how 'Taker was "the one guy he wanted," to be there with him during the tough days of the Monday Night War. This is just another sign that the boss trusts The Undertaker more than any other Superstar that isn't his son-in-law.

If you don't believe what we said, well continue on to read on. We'll address this again.

11 McMahon Beat The Undertaker at Survivor Series 2003


Vince McMahon's "Mr McMahon," character was a huge turning point in the Monday Night War. He made fans more invested in his product by booking himself to fight against the WWE's top stars. It worked to perfection when he feuded with The Rock and Stone Cold Steve Austin. It's a different case with 'Taker.

The two had a rather forgettable onscreen rivalry. Both men got in each other's way, with McMahon telling Undertaker he hoped that Brock Lesnar would "bury him six feet under."

The two settled the score at Survivor Series 2003 in a Buried Alive match. With The Undertaker on the edge of victory, Kane interfered and threw 'Taker in the grave to help The Chairman win the match.  To be honest, this match wasn't all that bad. Just another predictable finish is all.

10 The Undertaker Fought Through Hip Injury to Impress Vince


There are millions of wrestlers around the world that dream of reaching the WWE. But for The Undertaker, he had to go incredibly great lengths just to pray that Mr. McMahon would give him a shot in the company.

He faced Lex Luger in an NWA match back in 1990. The Undertaker was fighting through a dislocated hip injury, but decided to fight through the match. This is because he knew the WWE owner and chairman was in attendance that night and he wanted to impress him. It ended up working out just fine.

Is anybody really surprised by this? The Undertaker is a man who has wrestled well into his 50s despite all of the injuries he's had to deal with over the years. Fighting through that hip pain was the best decision of his career.

9 Vince Wasn't Originally Impressed By The Undertaker


The Undertaker (believe it or not) was in WCW during the late '80s. But Paul Heyman got in contact with Bruce Prichard (former WWE executive) and pitched the idea of bringing The Undertaker on board. Prichard saw him in Dallas and was thrilled with the idea of bringing The Undertaker on board with The Deadman gimmick. But here's one interesting thing of note: Vince McMahon wasn't that keen on Undertaker early on.

Here's what Prichard had to say regarding McMahon's original thoughts on Undertaker:

"He [Vince] wasn't high on Mark in WCW..And it wasn't like you were gonna get a great match out of Luger. Add to that a dislocated hip and it wasn't the greatest match in the world.

And Vince just saw a tall, redheaded basketball player. So there wasn't a lot of interest but then finally when we got the two of them together were they could meet, hard not to fall in love with him."

A key lesson for everyone is to remember you can't judge a book by its appearance. Also, first impressions aren't everything. The Undertaker has become a hands-down top-five wrestler of all-time.

But it wouldn't have happened if Vince immediately turned down the idea of bringing him on board.

8 The Undertaker Defended The Boss on a Plane


Over the years, we've learned about a ton of wrestling incidents that took place backstage. Enter Mr. Undertaker and Kurt Angle. This wasn't back stage, however. Rather, it was thousands of feet in the air.

During a backstage prank, McMahon unexpectedly jumped Angle just so he could tell everyone that he was the only guy to take down the real-life Olympic champion. In Angle's autobiography, he talked about an incident that took place on a plane where he tried got into a playful fight with the boss on a plane.

This awoke The Undertaker, who assumed that Angle was legitimately attacking the boss. So he got up and choked out Angle to stand up for his boss. Thankfully, 'Taker learned of the misunderstanding and the two patched things up backstage later on.

7 Vince Chose to End The Streak


There are plenty of theories as to whose idea it was to have The Undertaker's 21-0 streak come to an end at WrestleMania XXX against Brock Lesnar. For example, some believe The Undertaker wanted it to end because if the streak stayed in tact, he'd keep getting pushed to come back for "one more match," year after year.

Well, that's not the case. Surprisingly, it was entirely Mr. McMahon who chose to end The Streak. When he was questioned by Stone Cold Steve Austin as to whose idea it was, McMahon said he mad the call because he felt like it would help push Brock Lesnar's iconic status even further. He added how there weren't any other wrestlers suitable enough to beat Taker.

Given how Taker had already faced off and beaten most of the top stars already on the roster, it's tough to disagree with McMahon's choice.

6 The Undertaker Was Fine with the Decision


One would think that The Undertaker could simply say "no," to Vince about ending The Streak and walk away from the company altogether. However, 'Taker's willingness to do what was best for the company shined through once again. He was on board with the call and the rumors are he even chose Lesnar to end it.

The Deadman is a well-known fan of UFC and apparently asked Lesnar about having a match while the latter was with Dana White. The Undertaker didn't seem to have any problem letting the streak come to an end. He came out and put on an epic match while adding more to the legacy of Lesnar.

You see, so many wrestlers over the years refused to lose matches that could have altered their careers. The Undertaker wasn't one of them.

5 Vince Embraced Him Backstage 


Because of how tough of a call it was to have The Undertaker's streak end, one would think Vince would want to ignore The Deadman for a while and allow him to recover from the emotions coming along with the ending of The Streak. However, that wasn't the case as both men were seen hugging it out backstage.

This was just another reminder of how epic the relationship is between these two men. Vince obviously didn't feel great about having The Streak end, but one has to think about it from a business standpoint: Lesnar is 39 and his legend is only growing more and more with each icon he defeats. The Undertaker is on the verge of retirement. It made sense to put the newer/younger guy over in this one.

But the two obviously shared their respect backstage without a problem.

4 And Vince Helped Him to the Hospital

via mtv,

What some don't know and may forget is that The Undertaker legitimately suffered a concussion during his match against Brock Lesnar at WrestleMania XXX and had to get to the hospital after. McMahon was incredibly worried about his star wrestler and worked fast to get him to the medical center.

This meant that Mr. McMahon actually missed the end of the WrestleMania event, worrying more about The Undertaker's health. Given recent history, it doesn't sound Mr. McMahon-like, but it's just another sign of how much he values this man as a wrestler and a person.

It was easily one of the most emotional nights in WWE history for the fans and the wrestlers. But McMahon and Undertaker added a nice element of happy emotions when their close relationship shined through on this one night.

3 The Two Were Rumored to fight at a WrestleMania


The Undertaker has faced off against most of the main legends you can think of at WrestleMania: Ric Flair, Kane, Triple H, Randy Orton, Brock Lesnar, Shawn Michaels and others. Vince himself has gotten into feuds with the likes of Shane, Hulk Hogan, Triple H, Steve Austin, The Rock, and others.

We touched base earlier on them facing off at Survivor Series, but the two have been rumored over the years to possibly square off at WrestleMania. This would have been an epic match to many, but Vince hasn't been a wrestler in the ring for years and Vince now being 71 and Undertaker being 51, there's zero reason to believe a match could take place.

It's probably better that the two never faced off any way. Neither has been in their respective peak conditions for a number of years now. But 15-20 years ago, this would have been a dream match.

2 The Undertaker Almost Left for WCW


As we talked about earlier, The Undertaker's career started in WCW, but he was just a little-known jobber who didn't get around to doing much there. It wasn't until McMahon was introduced to The Deadman where the latter's career really began to take off. And now, think about the biggest stars of the Monday Night War.

Hulk Hogan, Kevin Nash, Scott Hall, Randy Savage, Lex Luger, Ric Flair, Bret Hart and others all went to WCW when Vince McMahon decided to move on from them. Chris Jericho, Rey Mysterio, Big Show, Triple H and others decided to side with WWE.

But The Undertaker was the one man who was Vince's loyal soldier all along. Kevin Nash talked about a time when they almost convinced him to join WCW in his biker gimmick, but 'Taker ultimately decided to stay loyal to Vince McMahon.

It obviously worked out for both, as WWE would win the Monday Night War and 'Taker's legend grew more after WCW was bought out in 2001.

1 Vince Calls The Undertaker His Favorite


It's not common for a boss to ever show their bias and preferential treatment. It's even more uncommon for them to ACTUALLY tell people who their favorite is. But for Vince McMahon, he hasn't kept it a secret:

"That would be Undertaker because of his loyalty, his longevity, and his extraordinary commitment to his character. He is such a professional and an extraordinary human being behind the character. He's committed to his craft and has worked through his injuries."

You just have to see how it all took place overtime. The Undertaker worked so hard to impress Vince, who was impressed pretty quickly from what he had to offer. The two worked hand-by-hand to destroy WCW. The Undertaker is easily the top wrestler Vince McMahon has ever had.

Without Vince, The Undertaker is not a big deal in the world of wrestling. Without The Undertaker, perhaps WCW wins the Monday Night War. And unlike Vince's rocky relationships with Hulk Hogan, Randy Savage, and other legends, he and The Undertaker have always stayed close.

It's a friendship like no other and surely one sports entertainment will never see again.

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15 Things You Didn't Know About The Undertaker And Vince McMahon's Relationship