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The Undertaker vs. Sting would have been virtually guaranteed had The Deadman jumped ship to WCW.Credit: WWE.com
WWE Network’s critically-acclaimed Undertaker: The Last Ride documentary has raised many questions among fans of The Phenom, specifically in regards to what could have been had he left WWE during the Attitude Era, one of the most pivotal—and profitable—points ever for the company.
Although The Undertaker had a brief stint in WCW from 1989 through 1990 as Mean Mark Callous, it was apparent he likely wouldn’t have fared well there and wouldn’t have been as successful as he has in WWE.
That doesn’t mean he never entertained the idea of jumping ship to the opposition during the peak of its popularity in the mid-to-late ’90s, though.
In a candid interview with Sam Roberts and Jim Norton this week, Undertaker revealed he came close to leaving WWE when the company was struggling both creatively and financially. He specifically mentioned being fed up with the outrageous gimmicks that were going around at the time and that WCW would have been willing to pay him the big bucks.
Ultimately, he stayed true to his WWE roots and became one of the biggest icons ever. Since the Attitude Era, he has reinvented himself on countless occasions, won multiple world titles and embarked on the most impressive winning streak of all time for over two decades at WrestleMania.
Needless to say, Undertaker made the right choice by remaining loyal to Vince McMahon and the rest of WWE. While fans will never know exactly what would have happened had he joined WCW during its most prosperous period, the following six things likely would have been guaranteed.
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As important as The Undertaker has been to WWE since 1990, the company would have carried on without him the same way it has with anyone else who retired or moved on.
The loss of Hulk Hogan in 1993 wasn’t a death blow, even though it led to some of the worst programming the promotion ever produced in the years that followed.
That was a transitional period, but it was then that Undertaker almost headed to WCW. Although its product wasn’t quite as hot as it would become around 1996 and 1997, it still had the legendary likes of Hogan and Randy Savage under contract and was making moves.
Undertaker (with a different moniker) signing with WCW in the mid-’90s would have generated big buzz for the company early on, but WWE would have been able to recover in time with the fresh faces it had coming up in the ranks.
Bret Hart left WWE in November 1997 and Shawn Michaels retired from the ring with a devastating back injury soon after, but the company still had Triple H, “Stone Cold” Steve Austin and The Rock on its roster. Those three would have been enough to carry the company into the new millennium given they’re once-in-a-lifetime athletes.
Undertaker being with WCW would have given it even more star power than it already had, but much like when Hart came over after the Montreal Screwjob, it wouldn’t have made much of a difference in the long run if he wasn’t utilized properly.
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Bret Hart has talked at great length on many occasions about how he much he hated his tenure in WCW.
Its failure to capitalize on the buzz he had coming out of the Montreal Screwjob got his run there off to a terrible start, but it wasn’t as if the company did anything of note with him after that, either.
Eric Bischoff hinted in an interview with 83 Weeks podcast (h/t EWrestling) that Hart’s lack of motivation was the main reason he didn’t do well in WCW, so perhaps The Undertaker would have been better off had he jumped ship instead.
Then again, the situation with The Hitman proved that no matter who it had under contract, the company’s creative direction was taking a turn for the worse by that point. It was misusing most of its top talent and focusing on few stars outside of the New World Order, so unless Undertaker started sporting the black and white, he would also have gotten lost in the shuffle.
That’s in addition to how the Undertaker character is just a much better fit in WWE because that was where it started. WCW would have attempted to recreate the character’s success but likely wouldn’t have been able to do it nearly as well as Vince McMahon.
That also begs the question of whether his “American Badass” gimmick would have been born earlier out of necessity. He could have completely reinvented himself much like Hogan when he formed the nWo and gone heel, but that may have also only had a short shelf life.
WCW would have found a way to creatively bury Undertaker one way or another, which would have hurt his legacy far more than anything WWE could have and has ever done with him.
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Imagine one of the most iconic wrestling rivalries in The Undertaker vs. Kane never coming to fruition.
More importantly, try to imagine Kane the character never being created and how much worse off the last 20-plus years in WWE would have been without them.
Their long-running rivalry throughout the Attitude Era (as well as their subsequent alliance) provided fans with some of the best pieces of storytelling in the company’s history. As over-the-top as some elements of it were, everything they did made them into how they are today.
Undertaker was already successful long before Kane arrived in October 1997, but having The Big Red Monster as his rival and later partner changed his career in a major way. Kane was the first person to make ‘Taker look truly vulnerable and pose a legitimate threat to him.
Beyond their unforgettable series of matches, Kane went on to win a world championship and work up and down the card with practically everyone. He has also been a staple on WWE programming since his debut and has enhanced the product more than most.
Before becoming Kane, Glenn Jacobs was going nowhere fast in WWE as Issac Yankem D.D.S. and Fake Diesel. The new character saved him, but there would be no Kane without Undertaker. The Attitude Era still would have existed without The Brothers of Destruction, but it wouldn’t have been remotely the same.
Mankind made a name for himself in WWE at Undertaker’s expense when he first showed up, so he can be included in this category as well.
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Dream matches are few and far between in today’s wrestling landscape, but it was fun for fans to fantasy-book certain stars from WWE and WCW against each other when the promotions were at the peak of their popularity.
Among the most desired dream matches leading that list was The Undertaker vs. Sting.
Both men served as pillars of their respective promotions and thrived at portraying “dark” characters. Sting’s silent “Crow” character made him a huge fan favorite, while ‘Taker never ceased to entertain the audience by vowing that his opponents would rest in peace.
It’s easy to assume they would have faced off at some point had Undertaker jumped ship to WCW, and while that is true, the chances of Sting ever adapting that persona are slim to none depending on the timing of ‘Taker’s move. If The Phenom came over before the nWo ever formed, there would probably be no need for “Crowd” Sting.
WCW then would have built to ‘Taker vs. Hulk Hogan at Starrcade 1997, which would have underwhelmed as well because of how nWo had such a stranglehold on the company and how they refused to ever look vulnerable. Undertaker vs. Sting could have happened soon after, but it wouldn’t have been the same if Sting didn’t have his vigilante character.
The prime time to book the bout would have been in the early 2000s when WCW shut down and Sting was a free agent. At a WrestleMania, it could have been breathtaking, but in a poorly-run WCW, it would have failed to meet the lofty expectations of fans and fallen flat.
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WCW annihilated WWE in the ratings every week for well over a year for a reason. Its programming was hot and exciting, and everything it did seemed to turn to gold.
That was, however, until it didn’t.
The nWo angle was eventually run into the ground, no new stars were being made, and the backstage politics started to take a toll on the product. For as excellent as a job as WCW did building up Sting to vanquish the vindictive heel stable, it was basically downhill for most of the show’s top stars from there (except for an elite few) from there.
The Undertaker undoubtedly would have held the world title a few times and been a difference-maker in the ratings for at least a little while, but so long as the same people were in writing the shows and in charge of creative, WCW’s fate would have been no different than what it ended up being.
Undertaker did phenomenal work for WWE throughout the Attitude Era, but he wasn’t the sole reason why it won the war with WCW. Even with him out of the question (and in the possession of the competition), WCW still would have been bought out and put out to pasture.
It’s not that Undertaker saw the writing on the wall when he refused to go there, but that instinct within him to stay where he was in WWE and see that character through proved to be the best thing he could have done.
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Although a majority of WCW’s top stars didn’t immediately sign with WWE at the start of the Invasion angle in mid-2001, everyone eventually came over, even if it was years later. That includes Sting who, despite never having a history with the company, finally made the jump in 2014 and had a year-long run for himself.
When WCW closed its doors for good in March 2001, The Undertaker would have been no different. If the nWo, Goldberg and Ric Flair weren’t a part of The Invasion, The Phenom likely would have joined them on the sidelines before inevitably returning “home” to WWE.
However, virtually nobody who jumped ship from WCW to WWE in 2001 is still active in the company today. They were all humbled by Vince McMahon and left for other promotions years later because it was clear they were never as loyal to him as stars such as Triple H, Shawn Michaels, “Stone Cold” Steve Austin and The Rock were.
Undertaker’s strong bond with McMahon over the past three decades is a major reason why he has stuck around for as long as he has. Without that, he presumably would have retired years ago or tried his luck elsewhere, as odd as it is to imagine him in TNA or Ring of Honor.
A case can be made for why The Deadman should have hung up the boots after The Streak was snapped in 2014 or soon after, but regardless of how fans feel about his current status, it’s undeniable that his decision to stay with WWE through thick and thin was well worth it for the many memories he’s created over the course of his illustrious career.
Graham Mirmina, aka Graham “GSM” Matthews, has specialized in sports and entertainment writing since 2010. Visit his website, Next Era Wrestling, and “like” his official Facebook page to continue the conversation on all things wrestling.