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The Undertaker's retirement has been a major topic of discussion among fans and the wrestling media alike in recent weeks. The first three episodes of The Last Ride documentary series have chronicled The Deadman's struggles with walking away from the business that he has dominated for decades.
We found out early on in the series that plans were for WrestleMania 33 to be The Undertaker's final match. He lost to Roman Reigns in the main event. Then he took off his hat and jacket, left them in the ring, and walked out of Camping World Stadium to a hero's send off. The match itself however, was not what Taker had in mind.
Unable to train properly for the match with Reigns due to an ailing hip, The Undertaker (real name Mark Calaway) admitted that he should not have been in the ring that night. After undergoing surgery to alleviate the pain in his hip, Calaway began training again and ultimately decided to give it another go at WrestleMania 34 against John Cena.
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Turns out, that match was a disappointment to Calaway for a completely different reason. He says he was in good enough shape to go out for a 20 minute match and got a quarter of that time.
He defeated Cena in what was essentially a glorified squash match. Had Undertaker gotten the time he desired, the match might have been enough to walk away. However, his yearning for something more coupled with his new found health led him down his current path with the company.
Will The Undertaker have that final match he's searching for?
The Undertaker is stuck in a revolving door of triumphs and disappointments in the ring as he searches for the right moment to be his last. Right now he's riding high following his victory over AJ Styles in the Boneyard Match at WrestleMania 36, but will it be the last time we see The Deadman compete? Not likely.
If one thing has been made clear in The Last Ride, The Undertaker is looking for that Shawn Michaels send off. The opponent, the location, the match, and the story all have to be right.
While the match with Styles, for the most part, received rave reviews from fans and critics both, I can't imagine The Undertaker having his final match without an audience present.
As time moves forward it's getting harder and harder to make Calaway's dream send off come to fruition. So I starting thinking. If I was booking the Undertaker's retirement match, how would I do it? Who would be the opponent? Well I asked those same questions to a few of my colleagues in the world of wrestling journalism.
The Undertaker has said when it comes to retirement it's his call to make, but it's still something fun to think about. If you had the power to book his final match, how would it go down?
Stephanie Chase - Digital Spy and Sportskeeda
Stephanie Chase is a freelance wrestling journalist and is a contributor here at Sportskeeda. She's a lifelong viewer and follower of pro wrestling and has extensive knowledge of WWE, New Japan Pro Wrestling, Ring of Honor, and All Elite Wrestling.
Stephanie's conducted a number of high-profile interviews with stars like Triple H, Jon Moxley, Paige, Charlotte Flair, Bayley, Mandy Rose and Otis. Her work has appeared on a number of outlets including Digital Spy, The Mirror, Huffington Post, The Sun, and Cosmopolitan. She also has her own YouTube Channel.
How would she book The Undertaker's last match?
"I will always be a creature of the night and, no matter how cool The Undertaker looks on his motorcycle, he will always be the Lord of Darkness to me. If The Undertaker was to have one final match and really call it a career, the man who should send him off is Aleister Black.
Black is Undertaker’s natural successor and a character who carries some of his same traits but can work for a modern audience.
Unlike Undertaker, Black’s not meant to have special powers. Instead he’s a man with an interest in the occult who embraces the darker side of life. The two characters have a connection that’s yet to be fully explored by WWE and Black is a much better fit for Undertaker than Bray Wyatt ever was.
I would love to see The Undertaker pass the torch (and maybe even his Ministry of Darkness) robe to Black. Of course this should take place at a WrestleMania and I’d give it around 15 minutes with a casket match stipulation.
It doesn’t even have to take place in the arena as, like the Boneyard match, they could do a great job of presenting something really cool and hiding Undertaker’s limitations if they pre-recorded it. The ending should be Black getting Undertaker into the casket and closing the lid on the character forever."
Sean Ross Sapp - Fightful
Sean Ross Sapp is the managing editor at Fightful.com and has previously been a feature and news writer for the likes of WhatCulture, Rant Sports, Cage Passion Sports, and Fansided. Today, he is one of the foremost knowledgeable analysts and trusted insiders in wrestling journalism.
Now The Undertaker has said before that he doesn't ever really see himself walking away from the business for good. So we can expect to see The Deadman in some capacity for years to come. Ross Sapp believes the emergence of cinematic matches could be a great way to keep The Undertaker alive and well long after his retirement match.
As for that match, count Sean in for giving the nod to Aleister Black as long as he properly benefits from it.
Would Aleister Black be able to capitalize on a win over Taker?
"While we've seen The Undertaker in a plethora of possible, career-ending scenarios, his final match should be against someone who can use that to take them to the next level.
All due respect to Brock Lesnar and Roman Reigns, they managed to benefit greatly from the WrestleMania win over Undertaker, but they were already main eventers. In order to "retire" Undertaker from in-ring competition, I think it needs to be established as such.
The Undertaker could even say "I'm not done fighting, but I'm done wrestling," to give the company excuses to keep him involved in cinematic aspects of the program, and to let people know what to expect moving forward from him -- the Boneyard Match style contests.
Aleister Black strikes me as someone who could heavily benefit from "writing off Undertaker," but is it in his personality type to benefit from it? Bragging about it for years to come would be a big part of the win.
A young, emerging heel would be the best scenario for such a situation. Even Brock Lesnar's successor as the next "Heyman guy" would be a natural pick, as Paul Heyman would get plenty of mileage out of another Taker accolade."
Matty Paddock - Sportskeeda and Daily DDT
Matty Paddock has been covering professional wrestling in the UK for the last four years, including the Independent and Daily Mirror. Matty’s work has been sourced by the Associated Press, BBC, Bleacher Report, Yahoo, MSN, CBS, Sports Illustrated and many more.
He's had the honoring of interviewing stars like Triple H, Roman Reigns, Stephanie McMahon, Cody Rhodes, Jon Moxley and a myriad of others.
Like many of us, Matty has thoroughly enjoyed the first episodes of The Last Ride series. He says the series has been brilliantly cathartic in slowly edging fans towards the conclusion that Mark Calaway needs to step away from the wrestling ring. Which is difficult for so many who have been heavily invested in the character over the last three decades.
How about an unconventional light vs. dark match up to send the Undertaker off?
"For my money, the only way he should do that is against Seth Rollins. You may consider that to be a fairly tepid choice, but here’s my reasoning:
The Undertaker doesn’t need to do a job on his way out. The idea that as a seasoned pro he should put over a talent on the up has already been exhausted.
WWE wanted to establish Brock Lesnar as it's main star at Taker’s expense a few years ago and had him end The Streak.
Roman Reigns was due to get the ultimate rub by retiring Taker in 2017 but, as we know, that failed to materialize. So let’s not worry about The Phenom trying to put anyone else over - it’s been done enough.
Secondly, Seth Rollins can withstand being beaten by The Undertaker. Credit to the former Shield member - he’s strong enough, established enough and over enough to take a loss at Taker’s hands and come back fighting soon after. Look at AJ Styles as an example of that. His Mania defeat hardly buried his career, even if he did find himself six feet under. In short - you’re doing Seth no damage.
Lastly, creatively it makes sense. Who better to go up against The Undertaker - a man who once called himself the Lord of Darkness - than The Monday Night Messiah? While the character of The Undertaker wasn’t necessarily created on a basis of faith, it has certainly touched on those themes, many of which Rollins has weaved into his current character. Having the two of them extolling the virtues of their respective ‘beliefs’ would make for one heck of a promo segment.
So there you have it. Let’s have The Undertaker and Seth Rollins tear the house down before the Deadman picks up the win. It won’t be a squash - Rollins deserves more and should get it - but at the end of the match, Seth is getting his hands folded over into his chest and pinned for the 1-2-3, one last time. As for when? Let’s say Survivor Series. The perfect dovetail to the career and story greatest wrestling character of all time. The same event, 30 years apart."
Tom Colohue - Sportskeeda and Daily DDT
Tom Colohue is one of Sportskeeda's top pro wrestling journalists. He started writing professionally in 2008 and has been covering wrestling since 2017. He's most well-known for the PWTorch Roman Reignsometer that started at that time.
Tom is also the co-host of Sportskeeda's Dropkick DiSKussions Podcast and posts weekly news updates on his YouTube channel.
The Undertaker was involved in the first match Tom ever watched as a wrestling fan and has been one of his favorites ever since. He believes the perfect retirement story for The Deadman was already told at WrestleMania 33, but that another great story can be told.
The culmination of the New Face of Fear
"For me, The Undertaker told a perfect story with Roman Reigns. Not just with the hat and coat being put down, the kiss to his wife and the stride off into the sunset but for me, the fact that he couldn't get up for the Tombstone was part of it. The sit up that he couldn't manage. That iconic Taker moment being missed. He didn't look like The Undertaker. He looked human.
Now I get that that's not what they were going for but for me that's the right way to do it. To go out not because it's time but because you are physically incapable of continuing. I find it a shame that they weren't able to stick with it but if the man can wrestle then that's his choice.
There aren't many now who could retire Taker but if that's what we get it should be someone with equal commitment to the character, equally infallible drive. For me, it has to be Bray Wyatt.
Nobody else has the charisma, the determination and the ability. If we are looking for someone who will carry on for decades being a character that is absolutely unforgettable, Bray is the man. No Firefly Fun House. No Boneyard. Two men in a ring. One of whom just can't go any more."
Adam Cailler - TWM Wrestling
Adam Cailler is the Head of PR and talent relations for TWM Wrestling and is also a journalist for the Jewish Telegraph. Adam has been a wrestling fan for over 20 years and has been covering WWE for over a decade now. In addition to TWM, his work was also featured here at Sportskeeda a while back.
While Adam enjoyed the Boneyard Match at WrestleMania 36, he feels a little cheated that we didn't get the Phenom vs. the Phenomenal One inside the squared circle. The writing has been on the wall for a few weeks that these two may not be done with one another. Maybe a big blow off match could be the last for The Undertaker.
What could Taker and Styles do in a straight up wrestling match?
"The story for this match is already brewing, and has been since before WrestleMania 36. The opponent should be AJ Styles. We've only seen the pair face off in a match once, and it didn't take place inside the ring – which is a crying shame.
To do, what could be an epic encounter justice, it needs to happen in the ring, in front of the biggest possible audience at WrestleMania 37.
The Undertaker said, on The Last Ride, that he would love to work with AJ, and I don't think the Boneyard match – which was quite incredible – would have satisfied his need to work with Styles.
The constant haunting of AJ over the last month or so has kept this story arc in the mind of the WWE Universe, and if done correctly, could be unbelievable in its pay-off.
There are those who talk about Undertaker's final opponent being someone young and upcoming, but looking at the roster, there is nobody who could realistically be given that torch.
Styles is young enough to be given that, to then pass it on in five or so years time, making the legacy of both The Undertaker and AJ Styles mean a lot more than it ever would have done had the legacy of just one of those men been given to someone who you don't know how their career will turn out.
Once again, looking at the roster, there really is, for me, no other option for Undertaker's final match."
Mr. Warren Hayes - Fightful
Warren Hayes is a wrestling podcaster who does not fear the reaper but has apprehensions about American cheese. He records his podcast, the Mr. Warren Hayes Show, live every Thursday evening on his Youtube Channel and he's also a regular contributor on the Fightful podcasts.
While others I've spoken to want to see The Undertaker go out in style with one final in ring spectacular, Warren is looking at the possibility of that just not being likely or even a possibility at this point.
While The Deadman is in better shape now than he was a few years ago, the longer his career goes on the more likely Father Time ultimately wins out. So maybe, a poetic ending at the hands of an old rival might be the best way to end his storied career.
A cinematic masterpiece might be the best way to go out
"If there is anything that the “Last Ride” documentary has taught us about the Undertaker, it’s that Mark Calaway’s body is broken and in pain. It is improbable to believe he could go out in his final match like the Deadman we all once knew. It cannot depend on athletic competition alone. Besides, there is a much more compelling story to be told, if he is put in a Firefly Fun House match.
Taker always said that he would want to go out on his terms, when the moment was right. But what if that moment had already passed? What if it was no longer up to him? What if he is forced to come to the deep realization that he has overstayed his welcome?
Imagine how chilling a Firefly Fun House match could be, as Bray Wyatt confronts him with the most terrifying reality of them all: that the Undertaker we knew has been gone for a while. That his final matches, like his ones against Roman Reigns, losing the WrestleMania streak, and the disastrous Saudi Arabia shows had tainted his career. Bray would confront Taker and eventually expose that the Undertaker’s true enemy, the one that kept him from having his legacy truly capped long ago, was WWE. Vince McMahon himself.
So, instead of fighting to the bitter end one more time, instead of succumbing to Vince’s final whim, Mark Calaway realizes that he will indeed leave on his terms, leaving Vince in a world without the Undertaker, and lays down for the Fiend, passing the torch to Wyatt in a moment both of dreaded self-realization and defiance.
Finally, the Undertaker earns his warrior’s rest."
Gary Cassidy - Sportskeeda and The BBC
Gary Cassidy is a freelance journalist and an official columnist for Sportskeeda. Gary is one of the go-to wrestling journalists in the UK, having had the opportunity to sit down with the likes of Triple H, Stephanie McMahon, Chris Jericho, Charlotte Flair, and Kurt Angle.
Gary also creates video content for BBC, writes for WhatCulture, and is regularly featured on the Wrestling Daft podcast as well as TalkSPORT's talkWRESTLING show.
Getting to know Gary over the past year I've learned he's never shy to share his opinions. When it comes to the subject of Taker's final match, Gary is of the opinion, that his opinion does not matter. He says however, wherever and with whomever The Deadman decides to end his career, it'll be good enough for Gary Cassidy.
Whatever the Phenom believes is the best way to close the book on his career
"The prospect of the Undertaker retiring is one I'm unsure will ever happen, but I believe we may find out how likely it is by June 21st, when the dust settles and the credits roll on Chapter 5 of The Last Ride.
For many years, I found the idea of the Undertaker retiring as a pretty impossible concept to comprehend.
I always thought closing the book in a WrestleMania match with Kane, and both men saying their goodbyes at the same time in an embrace after a singles match, would be the perfect ending to that saga. Of course, many will say the dream match with Sting is THE match we have to see.
However, after the Roman Reigns match, I think we had the perfect moment - from putting over a young talent on the Grandest Stage of Them All, to the Showcase of the Immortals taking the mortality of The Deadman as he broke character for the first time ever.
Now, though, much like The Deadman's own wife, Michelle McCool, acknowledges in the monumental docu-series, Undertaker seems - or seemed - to be trapped in a vicious cycle of either having an amazing match and wanting another, or having a sub-par match and needing another for redemption.
One interesting note during The Last Ride was that Taker said he wished he could have worked with AJ Styles, so maybe the series ends in the revelation that we've already witnessed the retirement match just mere weeks ago - but for me, the ending is no longer important.
Via the Undertaker, Mark Calaway has given us 30 years of entertainment, enigma and mystique that will likely never be seen again. Whenever The Deadman decides it's time to hang up his boots, or whether he even does at all, is completely fine by me."
My Final Thoughts
I have gone back and forth on this subject several times. I have read the statements from my fellow journalists. I think I have an idea of what the Undertaker is looking for in a final match. The truth of the matter is, all I have is an educated guess.
As of this writing I don't even think The Undertaker knows when or where his last match will be, or with whom. He may not even realize it until it happens.
I truly believe the emergence of cinematic matches will be able to elongate The Deadman's career by a couple years at least. Maybe it also gives us the possibility of seeing the dream match against Sting that fans have been waiting decades to see. Even if that happens, I don't feel like that would be the right send off.
Taker's last match should be in front of a sold out crowd. Not just any crowd either. It should happen on The Grandest Stage of Them All in front of 70,000 plus screaming fans at WrestleMania. There just isn't any other place for the most prolific WrestleMania performer to end his career. But against whom?
The hard fact is as the years go by, the more difficult it will be to find that perfect opponent. There are a number of Superstars I wish could get a one on one shot at The Undertaker - Aleister Black, Seth Rollins, Tommaso Ciampa, The Demon King Finn Balor, and Drew McIntyre just to name a few.
There's only one opponent that's fitting for the end of The Undertaker
For me personally. I think the perfect ending to the story was told already, but it was ahead of it's time. When Bray Wyatt met the Undertaker at WrestleMania 31 he was billing himself as the "New Face of Fear". It was tremendous marketing and another missed opportunity for Wyatt to launch his career into the next level. Unfortunately for Bray, on the heels of Taker's first loss at WrestleMania, he was The Phenom's bounce back opponent.
Fast forward to today, and Bray Wyatt's career has finally reached that next level. He's one of the top stars in the company. Despite being a heel, The Fiend is one of the most over characters in WWE. Not only that but with the mystical powers at Wyatt's finger tips, he's the closest thing to The Undertaker that we're likely to ever see in this day and age.
The Fiend has a list and one by one he's checking names off that list. Finn Balor, Seth Rollins, Daniel Bryan, and John Cena have all felt the wrath of Wyatt's sadistic alter ego. I believe the perfect story to tell is not so much the one of the Undertaker's final match, but of Bray Wyatt's ascension as the true "New Face of Fear".
The final match of The Undertaker's Hall of Fame career should be in a battle between the biggest forces of evil wrestling has seen over the last 30 years. It's a battle that The Undertaker will fight valiantly, but will ultimately lose. The Fiend should end the career of The Deadman so that Mark Calaway, and the soul of The Undertaker, can finally rest in peace.
What do you think? Who should be The Undertaker's final opponent? Follow me on Twitter and let me know!
