The Magnificent Seven: The 7 Worst Undertaker Rivalries

Whether or not you personally like him, or agree with his choice not to retire coming out of WrestleMania 33,, there’s little arguing against The Undertaker as one of the biggest stars and most important figures in WWE lore. Based on longevity alone, the guy is a key player in wrestling history, and he has managed to evolve nicely across different eras of WWE programming.

The Undertaker’s career has included rivalries revisited across eras and gimmicks, like his programs with Kane, Hulk Hogan, Brock Lesnar, and Shawn Michaels, each of which had at least one iteration that was pretty excellent. He also had more contained great feuds opposite guys like Mankind, Batista, and Edge. This column looks at the other side of the coin, though. Across nearly three decades, it’s little surprise that The Dead Man would have some stinkers on his resume, and this column is looking at seven of his dirt worst rivalries. This countdown considered storylines and match quality, with longevity as a secondary concern for often making matters worse. As always, my personal opinion weighs heavily.

#7. JBL

There are those times when real-life close friends make the best in-ring rivals. It was the case for Triple and Shawn Michaels, for example, when HBK came back from his first retirement, and it worked for Bayley and Sasha Banks back in NXT. JBL has publicly laid claim to The Undertaker being one of his closest friends, citing on the WWE Network’s Bring it to the Table that The Dead Man was one of the groomsmen at his wedding. Their feud, however, over JBL’s WWE Championship, left a lot to be desired.

JBL isn’t exactly known as a guy who produced four-star or better matches, but his series with The Phenom suffered, in particularly for the uncomfortable dynamic of JBL still being unproven as a main eventer, and WWE being invested enough in protecting The Undertaker that JBL never would pick up a decisive win on him. So, we were left with a series of just OK matches, none of which had real finishes, all of which felt like placeholders as JBL’s title reign loped along. To be fair, I’m not one to rip on JBL too hard for this period in his career—I actually thought he was a decent enough champion, particularly for having been hot-shotted into a new gimmick and straight to the title so abruptly. This program, however, represented the worst of WWE trying to push a fresh main event act while not being willing to sacrifice a legacy main eventer.

#6. Kamala

I was just a kid when the WWF started rolling out the card for “The SummerSlam you thought you’d never see” in 1992. The British Bulldog challenging Bret Hart for the Intercontinental Championship was intriguing, and while Randy Savage had battled The Ultimate Warrior before, it shared a special novelty for featuring another unusual-for-its-time face vs. face matchup.

The Undertaker vs. Kamala was a fresh match, too. The Dead Man was still relatively new to working face, and the WWF hadn’t yet made him battling monster heels into a pattern, so it remained interesting to see what a matchup like this might hold—especially considering Kamala was freshly returned to the WWE landscape, and a compelling super heavyweight threat.

WWE didn’t book this feud all that seriously, though, leaning heavily into the dynamic that Kamala was frightened of The Dead Man, and thus never posing him as a serious threat to him. The Undertaker beat the Ugandan Giant by disqualification in under five minutes in that initial SummerSlam bout, to build to a just-over-five-minute Casket Match to blow off their feud at Survivor Series. In many ways, this program bespeaks its time, as the WWF struggled to find its footing in the aftermath of Hulkamania, and clumsily strived to be family friendly. Thus Kamala wasn’t going to be a legit monster, but rather take a step toward a comedic face turn, while The Phenom wandered along as a largely directionless upper card act.

#5. Diamond Dallas Page

There’s no two ways about it: the Invasion angle that saw WCW (and ECW) alumni storm WWE was a disappointment. Some of that’s a matter of questionable creative, and some of it comes down to the realities of business as so many of WCW’s marquee stars had the opportunity to let the clock run out on big money deals, then sign with the WWF at their leisure, rather than making the leap right away. There are but a handful of dream matchups the WWF did successfully assemble in that first half year of mixing rosters. The Rock vs. Booker T? That made sense enough. Lita and Trish Stratus vs. Torrie Wilson and Stacy Keibler? A fun enough side attraction.

The Undertaker vs. Diamond Dallas Page? Of all of the WWF vs.WCW sub-pairings in the interpromotional war, this one had legitimate top-shelf stars whom there was fair reason to believe could do something special together. That’s especially so while The Dead Man was working his Biker gimmick, and thus was a bit more human and vulnerable than he’d be at most other stages of his WWE tenure.

However, The Undertaker vs. Page was a total and utter failure.

Rather than leaning into DDP’s unique personality that earned him an unlikely run to the top of WCW, the WWF plugged him into a generic heel stalker gimmick, terrorizing The Phenom and his wife.To make matters worse, The Undertaker would dominate the feud to follow, with Page consistently playing overmatched. The issue culminated in a steel cage tag team match, pitting The Undertaker and Kane and Page and Kanyon. While there was some pleasure in seeing The Brothers of Destruction completely run roughshod over heels who needed their comeuppance, it was nonetheless the final exclamation point on Page getting misused and buried in the early stages of his WWF run.

#4. The Million Dollar Corporation

Let’s start out on this note: for those worried I forgot about The Fake Undertaker, I opted to roll him into this countdown entry. His one match with the real Undertaker would only bring him to the fringes of this week’s countdown, but in the context of The Dead Man worrying with Ted Dibiase’s faction, it’s more than worthy of a mention.

As Ted Dibiase transitioned away from in ring performance, the WWF did the sensible thing in re-casting one of its great talkers and characters in a managerial role, on the premise that he used his vast fortune to pay a roster of heels to do his bidding, and to vicariously win him glory in the ring. It was a sound idea in theory, but between the talents available at the time and the WWF’s booking, it turned out to be a pretty lame stable, with Sycho Sid as its lone real headliner, and guys like Bam Bam Bigelow, King Kong Bundy, Kama, IRS, and Tatanka filling in the reasonably imposing, but wildly underachieving ranks. In over two years, the group collectively never actually won a single title or PPV main event.

One of the group’s signatures, such as it was, was jobbing out to The Undertaker, who worked his way through Bundy, Kama, and IRS in featured programs. Casting an upper card face against a top heel manager’s goons is traditional enough, but none of Dibiase’s men ever really posed a threat to The Phenom, and The Undertaker’s dominance over them felt a lot like treading water until WWE had something more meaningful for him to do.

#3. The Great Khali

The Great Khali was not a good wrestler, but unlike some critics, I’ll actually give WWE a pass for pushing him as a top guy and even putting the World Heavyweight Championship on him when he was surrounded by injured headliners. At a legit 7’1” and musclebound, he was enough of a spectacle to warrant a push and was serviceable in his role as a monster heel, followed by his run as an affable giant.

Unfortunately, The Undertaker got saddled with Khali’s first main event feud, and it was a classic case of it being better to book a smaller wrestler against a giant to play up each one’s unique look and wrestling style, rather than trying to shove together two more comparable talents. While The Phenom was a strong worker by that point in his career, with a more diversified offense and better equipped to sell than he had been earlier, he was nonetheless only able to do so much with Khali.

The resulting matches were poor on the whole, but what critics may remember most was their first PPV collision at Judgment Day 2006, in which Khali dominated, picking up perhaps the most decisive and one-sided victory over The Undertaker in the Dead Man’s career. That the Dead Man would give up a loss like that to such an underwhelming talent still leaves a bad taste in plenty of people’s mouths.

#2. King Mabel

Mabel was a 6’9”, reasonably agile 500 pounder. As such, it makes complete sense that WWE would give him a whirl as a main eventer, and all the more so as a monster heel. Most compelling of all, perhaps, he was around when WWE was trying to push Diesel as the face of the company. Big Daddy Cool met Vince McMahon’s vision of a physical super human with good looks to boot, but at nearly seven feet tall and three hundred pounds, it was difficult to generate sympathy for him. Thus, Mabel came across as a fitting rival to pit against Diesel, and the King of the Ring tournament was as organic of a way as any transition him from a tag team guy to main event bad guy.

OK, so the logic checks out up to that point, but unfortunately Mabel wasn’t up to the featured spot in terms of in ring talent, and Kevin Nash wasn’t in a position to carry anyone to a classic. The result was a lukewarm feud, culminating in a pretty terrible SummerSlam main event match.

In the aftermath, WWE still needed to do something with someone of Mabel’s size, and especially after he’d been built with the King of the Ring victory, and so he transitioned to working The Undertaker. Unfortunately, The Dead Man wasn’t able to get much more out of the giant, and worse yet suffered a shattered orbital bone off of a leg drop gone wrong. Mabel was big enough that small errors had big consequences, and so The Phenom was subjected to wearing a Phantom of the Opera style mask to protect his face in the months to follow, as their terrible feud lurched on.

#1. The Giant Gonzalez

Over time, The Undertaker had a number of monster heels debut opposite him, build to feuds with him, or transition to him as a step down from a more proper main event run. Fewer are those acts that feuded exclusively with The Dead Man. The Giant Gonzalez is the prime example of this less ordinary, inauspicious category.

Gonzalez debuted during the 1993 Royal Rumble, not as an entrant, but rather just to take out The Phenom and launch their program. They’d go on to the worst of The Undertaker’s WreslteMania streak matches—a plodding, clunky affair that culminated in Gonzalez getting DQed for subduing his opponent with choroform. They’d go on to blow off their rivalry at SummerSlam in what was billed as a Rest In Peace Match that felt a lot longer than its eight minutes, and culminated in The Dead Man anticlimactically putting away the big heel with a flying clothesline. Afterward, Gonzalez looked to turn face, arguing with manager Harvey Wippleman, in a turn that never really went anywhere before he left the company in October.

Billed at 8’8”, and truly 7’7”, WWE’s interest in Gonzalez as a spectacle of a heel was fair. The guy just didn’t have any tools beyond his height to succeed as a wrestler, though, and the fact that The Undertaker was focused on this guy for the three biggest shows of year is a historical abomination.

Which rivalries would you add to the list? Roman Reigns was my top runner up. Let us know what you think in the comments.

Read more from Mike Chin at his website and follow him on Twitter @miketchin.