How The Undertaker’s unique relationship with Vince McMahon, surgical success led to his WWE return

Three years ago, The Undertaker was done. For good. At least, he was supposed to be.

At WrestleMania 33 in April 2017, the man legally known as Mark Calaway — who by that point had been wrestling for the better part of three decades — had every intention of leaving his in-ring career behind and continuing with the rest of his life.

After falling to Roman Reigns in the main event of WWE’s biggest show of the year and suffering just the second loss on his pristine WrestleMania record, The Undertaker left his robe, hat and gloves in the middle of the ring. That was supposed to be the final time he would lace up the boots and battle it out for WWE. 

“That was 100% real and me saying goodbye,” Calaway claims during his acclaimed limited documentary series “Undertaker: The Last Ride,” the second episode of which will debut Sunday at 10 a.m. ET on the WWE Network.

But even in that moment, as Calaway literally left his on-screen persona in the ring, his performance in that match gnawed at his mind. Calaway was slow, immobile and lacking the explosion that made him such a legendary superstar, largely due to the fact that he was putting off a needed surgery on his right hip.

The climax of the match, in which Reigns was supposed to reverse a Tombstone Piledriver — The Undertaker’s signature finishing maneuver — was clearly botched as Calaway was unable to do his part and spring his body up into the air. He fell — twice – and the end of the match was exceedingly lackluster because of it.

“There’s the utter disappointment of the performance that I just gave, there’s the searing pain that’s running down my leg coupled with the fact that this is the last time that I’m going to come and be on this stage in this manner. I don’t think there’s anything any more real than me putting the gloves and the hat and the coat down,” Calaway said.

In the episode, Calaway is clearly disgusted with himself as he watches the match back for the first time nine months later in January 2018. Sunday’s show covers his long, unexpected return to the ring, which was not as clear a path as fans may have believed.

“It reaffirmed 10 fold everything that I thought. I looked old. I looked slow. I was overweight. I couldn’t move. It just wasn’t Undertaker-esque, I guess, in any sense, really. I had one match too many,” he said watching the match. “… So that’s when the wheels started turning that I need redemption.”

In that nine-month span, which included the right hip procedure four weeks after ‘Mania — his 16th career surgery following one on his left hip, rotator cuff, bicep, pectoral, both eye sockets and others on his knees, fingers and other areas of his body — Calaway claimed he had no intention of gearing back up to get in the ring at WrestleMania 34.

Except, he had every intention.

Awake in his hospital bed following his surgery, during which he went under anesthesia to his own Undertaker entrance music, Calaway was already talking to wife Michelle McCool, perhaps a bit tongue-in-cheek, about performing in New Orleans just 11 months later. 

There were a couple things standing in Calaway’s way. Primarily, his health and wellness. Not wanting to be a parody of himself, he understood how poorly he performed against Reigns despite not yet watching the match back. It hurt him not only professionally but personally as a long-time locker room leader who aimed to put over the WWE’s biggest star on his way out the door.

“I feel bad for Roman. You dream about that match — to be in that match tearing the house down. I wasn’t able to give him that. That bothers me. I can make excuses all day long. Excuses are like assholes, everybody has one,” Calaway said the following January. “[Watching the match] It’s like I don’t even know where I’m supposed to be. I haven’t spoken to him about it. He’s probably looking at me right now, thinking, ‘What was that guy all about?’ Really disappointing. … I’m sure he [thought that] when it watched it back. I feel like I need some redemption for that performance.” 

Vince McMahon, WWE’s famed chairman and CEO, was more than aware that Calaway was a shell of his former self that night. Reigns, who in 2017 was just over six years into his career but had been positioned as WWE’s signature superstar since 2015, knew it, too.

“It’s like heartbreaking. It affected me. It made me emotional. it made me want to cry,” he said, knowing what The Undertaker wanted to do but was unable to provide for him in that match. “I don’t regret anything. Was it perfect? No. We were in the moment and, as live television performers, anything can happen.

“To be able to do [as much as he did], it’s just all coming back on his character. It’s all coming back to the responsibility that he holds and that he succeeds at. If there’s something that has to be done and there’s a goal at hand, the man gets it done, plain and simple. I think that it couldn’t have been easy. I couldn’t imagine that decision or being at that point in my career or my life to where this is the last one. It’s still hard to fathom.”

Three months after his right hip surgery, as outlined in the second episode of “The Last Ride,” Calaway traveled to WWE’s corporate headquarters in Stamford, Connecticut, to meet with McMahon in August 2017. While his WWE contract had expired and it was a bit of a formality that Calaway would agree to remain with the company in some manner, there was no commitment that The Undertaker would return to the ring.

Calaway admitted that his tank was empty, but he also struggled to completely eliminate the idea of performing again. And considering he was about to enter negotiations with McMahon, with whom he has an incredibly close personal relationship, Calaway knew ahead of time that the meeting may take an unexpected turn.

McMahon, despite his reputation for being a demanding boss, has a legendary soft spot for those most loyal to him. And perhaps no one has been more loyal over a longer period of time than Calaway, who stuck by WWE in the mid-1990s when many of McMahon’s other top stars bolted for far more money and far less work with competitor WCW.

“Undertaker, Mark Calaway is the most loyal performer I’ve ever dealt with. He is the kind of man you would want — literally and figuratively — in the foxhole with you,” McMahon said.

The Undertaker never left WWE, and neither Calaway nor McMahon has forgotten that.

So while Calaway had no intention of getting in the ring again, and he asserted that McMahon “is going to want what’s best for me physically [and] mentally,” he had been in enough meetings with the man to know that he must expect the unexpected.

“I gave up on strategizing meetings with Vince a long time ago. I’ve been so dead set in what I was going to do and say in a meeting. Walk out, the door shuts behind me and then [I] realize, ‘I got absolutely nothing that I meant to say out,'” Calaway said.

McMahon holds a special place in Calaway’s heart. He named his son, Gunner Vincent, after his boss. Other than his father, Calaway claims no one has been more influential in his life. “He’d be the first one to pat you on the back but also the first one to kick you in the ass when you needed it,” he said.

Calaway later added: “I love Vince to death. I would take a bullet for the man. Honestly, I would. Yes, he’s my boss, my friend. He’s been like a dad. He’s been like a brother. He’s been it all to me.”

McMahon, asked by “The Last Ride” producers to share his personal thoughts about Calaway, immediately teared up. He then cut off the question, motioning his hand across his neck. “Can’t do that,” he said.

As history bore out, Calaway re-signed with WWE, but it is revealed in the documentary that he only told McMahon he would be available in an emergency situation for WrestleMania 34 in New Orleans. Calaway had not tested his surgically-repaired hip, nor did he feel the rush of momentum to redeem himself from his performance the year prior in Orlando, Florida, despite knowing deep down that he needed to.

That January, backstage at the annual Royal Rumble pay-per-view watching his wife compete in the women’s signature match, the wheels began turning for Calaway. He even commented on a match being wrestled by AJ Styles, his eventual opponent two years later at WrestleMania 36, noting that he wished he got to work with him before hanging up his boots because he reminded him of Shawn Michaels.

McMahon called Calaway after the show, suggesting a match with John Cena if he felt The Undertaker could go. That led to Calaway watching his match with Reigns and knowing he had to give it another shot — if his body was up to it.

The WWE storyline leading into the Taker-Cena match mimicked real life. Cena spent weeks calling out Taker on television, claiming if he did not fight him at ‘Mania, he would only attend the event as a fan. In actuality, McMahon gave Calaway four weeks to make a decision, saying he needed to know by the conclusion of the Elimination Chamber PPV in February.

In the meantime, McMahon sent an entire WWE ring down to a warehouse in Texas so Calaway could train. Once his cardio had picked up, Calaway knew he would be able to perform at a level that not would far exceed his 2017 form. So he sent a text message to McMahon during the Elimination Chamber show to commit to WrestleMania.

“F— yeah!” McMahon supposedly replied.

WrestleMania 34 was a healing experience for Calaway in mind, body and soul. He entered the event the best he had felt in a decade again with the intention of it being his swan song.

“After last year’s performance, I think there was a lot of reason to doubt. That’s not how I want to be remembered,” he said. “Yeah, it’s for the fans, but a lot of it is for myself and my pride and the legacy that I want to leave in this business.”

Taker’s short match with Cena repaired his image in front of fans and gave him confidence to go again, but Calaway sought out a receptive and forgiving Reigns afterward to repair his conscience.

“I feel so bad about last year. I just want you to know that bothers me,” he told Reigns backstage. “I didn’t have it. You know that.”

Calaway then met up with McMahon, and the two had a loving embrace that has become almost an annual ritual.

“None of this happens without him. He gave me an opportunity a long time ago. Obviously, he changed my life,” Calaway said. “It’s something I do every year: give him a hug, tell him, ‘thank you.'”

The well-received performance against Cena gave both The Undertaker and Calaway himself new life. Moments after his match, Calaway told McCool he was ready for the following year’s show.

As “The Last Ride” will play out, this unexpected yet successful final wave of The Undertaker’s career is met with more peaks and valleys, more successes and utter disappointments.

It feels as if it is headed for a crescendo, the announcement or intimation of one final match at an upcoming show, perhaps SummerSlam, Survivor Series (where The Undertaker made his WWE debut) or WrestleMania 37, scheduled for Los Angeles in 2021.

But as we have learned, when it comes to Calaway and The Undertaker, the end of the road always seems to be a bit further than we expect.

The second episode of “Undertaker: The Last Ride,” a five-part limited documentary series about one of the most private superstars in WWE history, will be released on Sunday at 10 a.m. ET on WWE Network.

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