The Undertaker: How It Could Have Gone Instead

Our writer goes full ‘Butterfly Effect’ on critical moments in The Undertaker’s 30-year existence.

The Undertaker & Brock Lesnar

This piece was originally written during our ‘Undertaker Weekend’ in June 2020. We are republishing this ahead of Undertaker’s ‘Final Farewell’ at Survivor Series.

There’s no denying that The Undertaker is one of the greats, a future Hall of Famer and a role model to wrestlers, fans and everyone in between.

As with anything, however, there’s no doubt even he’d admit a lot of ‘right place, right time’ played a huge factor in his (and anyone else’s) career.

With Hooked On Wrestling celebrating the last chapter of the Last Ride being released this weekend on WWE Network I wanted to make sure I wrote a decent piece about the Undertaker as he’s always been in my Top Three of wrestlers (along with The Ultimate Warrior and, interchangeably between them all, Jake the Snake, Jeff Hardy, Owen Hart and most recently, Pork Chop Cash).

There’s been a hell of a lot of articles written about the ‘Taker over the years and so I decided to take a slightly different look, a look at a few big points in his career that could’ve kept him from being the legend that he is today but ones that might not be entirely obvious.


HOW THINGS WENT: Wrestling as Mean Mark Callous in WCW, the Undertaker had a few matches but nothing major apart from one against a man called Sting and another against Lex Luger at the Great American Bash 1990. The latter is a decent match to watch, especially if you’ve only known him as the Undertaker. Watch for the height he gets as he leapfrogs the Total Package.

Someone who wasn’t impressed however, was Vince McMahon (I wasn’t impressed that the ‘Taker was pinned after a clothesline).

McMahon had been shown the tape of Mean Mark from that event by Paul Heyman but it wasn’t until they met in person that McMahon was convinced enough by the guy to offer him a contract.

BUT WHAT IF: Imagine though, if you will, if they’d never had the chance to meet up? McMahon would’ve carried on not thinking that Mark Calaway was worthy of WWE and so he would’ve stayed in WCW and as he is a loyal employee he could’ve feasibly stayed with that company until they were bought out by WWE.

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No WWE contract, no Undertaker character. He would’ve stayed as Mean Mark and as WCW didn’t have the best track record of knowing what to do with wrestlers he might’ve hung around the midcard, never having a decent shot to grow and evolve as a wrestler. Due to the egos running rampant in the company in the late 90’s, I’d hazard a guess he absolutely would not have become the locker room leader that he did.


HOW THINGS WENT: Jobber, unknown, tomato can, stiff, jamoke, no-name: however you know them you know they aren’t going to win. Back in the day they’d usually start off in the ring with nothing but a brief flash of who they were and you knew that they were there to do the job (hence: jobber) then go home with a few bruises.

Very often they’re local talent getting a bit of television time and a decent story to tell but there’s other ones that have one time or another been a decent superstar but have been shunted down the card in favour of putting over other, up and coming wrestlers.

Ryback a few years ago was on a monster push, beating two jobbers a week and destroying everyone but due to whatever reasons found himself losing week after week. Another notable one was Tito Santana. A huge star in his own right in the 80’s and 90’s, he ended up losing more than he won.

A huge win Santana had that you might not be aware of, but seeing who this article is about you might see where this is going, was against the Undertaker. The match was in Spain in 1991, just a month before the Undertaker would win his first ever WWE(F) championship. In fact, it was the first ever time the Undertaker had been pinned!

BUT WHAT IF: What if Vince McMahon was reminded of the guy that he didn’t like when he saw him in WCW? McMahon has a history of last-minute mind changes and isn’t afraid of deciding matches need to end differently or that certain wrestlers need to be going in a different direction.

In his autobiography, Mick Foley mentions how professional and selfless the Undertaker is when it comes to his matches and other wrestlers so it’s no stretch of the imagination that if McMahon had told him that he wasn’t going to win the big belt any longer but instead he would be used to enhance other talent and make them look good then he would’ve happily gone along with those new plans.

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Wouldn’t you? If you’re after your dream job and you have to convince the boss to give you the job after they said no, you want to keep them sweet so you nod along and agree to whatever they say until you’ve got your feet under the table but in the WWE when you’re settled into the part of being a jobber it’s very hard to become a World champion (Jinder Mahal aside).

This results in the Undertaker losing to Hulk Hogan at Survivor Series and then carries on through the next few main events. It still looks like WWE is giving him a decent push, at the Royal Rumble 1992 they still have him eliminated by Hulk Hogan but as he now has never beaten Hogan it’s expected.

At Wrestlemania the Undertaker still has his match against Jake the Snake Roberts but as he’s on a losing streak, Paul Bearer turns against the ‘Taker and sides with Snake who wins after knocking out the Undertaker with the urn.

Jake the Snake and Paul Bearer are announced as the true faces of the devil and bury the ‘Taker once and for all at Summerslam and the Undertaker from then on is never seen as a true threat for any championship and as a result starts to lose week after week on Superstars.

Sites such as this one have him on a list of the All Time Greatest Jobbers coming second to the Brooklyn Brawler but one above Louie Spicolli. And this writer becomes obsessed with The Undertaker, not Pork Chop Cash.

The Streak

HOW THINGS WENT: At Wrestlemania 25 the Undertaker and Shawn Michaels put on an absolute classic of a match full of great storytelling, emotions and big moves. One that went wrong, however, was the Undertaker’s over the top rope ‘suicide dive’ aiming for Michaels but taking out a cameraman instead.

The Undertaker went down vertical as the cameraman was supposed to be more of a landing pad than he ended up being and luckily the ‘Taker wasn’t too badly injured, was able to shake it off and finish the match.

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BUT WHAT IF: The cameraman is even WORSE at timing and doesn’t get anywhere close to the flying Deadman. As it is, he only gets his hands on him and possibly changes his trajectory just before landing, but what if he misses completely and the Undertaker goes straight down, head first?

He’s knocked cold and the match is awarded to Michaels as the Undertaker is no longer able to compete. The Streak has been broken but everyone agrees that 16 matches at Wrestlemania without a loss will never be bested. A few months later the Undertaker makes an unexpected appearance on RAW to announce his retirement.


HOW THINGS WENT: The absolute party classic ‘Slam Jam’ was released by WWF Superstars in 1992. If I could’ve written anything in my life, it would’ve been this. Just reading the lyrics gives me goosebumps, lines such as:

[Bret Hart] ‘The World Wrestling Federation today, slam slam.’
[The British Bulldog] ‘The World Wrestling Federation, Hah, slam, hah hah, Slam, Slam Jam, Hah.’
[The Undertaker] ‘The Undertaker says… Slam.’ 

Inexplicably, the single is overlooked by all the major awards.

BUT WHAT IF: It’s recognised for the piece of art that it truly is. It goes global and tops the charts in every country in the world, winning a Grammy, an MTV Music Award and for some reason an Oscar.

Repackaged as Grand Daddy Deadman, the Undertaker embarks on a solo career and unites the world through music (I’ve possibly been watching Bill and Ted’s Bogus Journey while writing this).


There’s a million and one other ways that could’ve kept him from being who he is, from Shawn Michaels never ‘losing his smile’ and retiring which left the Taker able to show what he could do as a main event star, to sticking with his original career choice of becoming a basketball player.

All I know is it worked out well for him, very well for WWE and amazingly well for wrestling fans as a whole.

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