How Triple H, Undertaker, Shawn Michaels Crafted Epic 4-Year WrestleMania Saga

Kevin Wong@@kevinjameswongFeatured ColumnistApril 4, 2019

Credit: WWE.com

From WrestleMania 25 to 28, The Undertaker, Triple H and Shawn Michaels put together an ambitious narrative saga that spanned four years and told an incredible story about pride, obsession and the difficulties of getting old.

For all three, it represented the "End of an Era." For the WWE Universe, it remains a stirring argument for professional wrestling as theatrical art that's unlikely to be duplicated in the near future. It was lightning in a bottle, and that doesn't strike twice in the same spot.

Credit: WWE.com

Enter Stage Right

The three men involved in this narrative arc need no introduction; they are all first-ballot WWE Hall of Famers, and their accolades are ubiquitously known. What's important is the context of their careers in 2009, when this epic began.

Michaels was coming off a storyline where he was employed and psychologically owned by JBL, who bailed him out of financial ruin and subsequently controlled every aspect of Michaels' career. But Michaels escaped his debt and contract after winning a match against JBL at No Way Out. Michaels seemed whole, happy and content with his life, having won back both his name and the rights to his career.

The Undertaker was still a weekly performer. Since returning as his Dead Man character in 2004, he had made efforts to meld his fighting style into a hybrid of all prior eras.

He retained the punches from his biker days, blending them with the signature moves from his Western mortician iteration and the fire and lightning from his Ministry period. He also incorporated MMA moves to complete the package and modernize the character for a new audience.

Triple H was still dealing with the fallout of his Evolution stable. Batista had double-crossed him several years prior, and Randy Ortonnow heading up his own Legacy stablewas attacking members of Triple H's family.

The character was vulnerable in a new, more obvious way. He had to care about people other than himself. He had to accept responsibility for the monsters he had created.

In 2009, Undertaker and Michaels were in their mid-40s. Triple H would turn 40 that July.

Against this backdrop, Michaels got himself booked in a match against The Undertaker at WrestleMania 25. The expectations were high, but not remarkably higher than the other "Beat The Streak" matches that came before it. In fact, on the Two Man Power Trip podcast, referee Marty Elias recalled that the original Mania plans only allotted 15 minutes for this match.

The weekly build reflected the level of seriousness. It featured some old-school camp, like when Michaels cut a promo with funeral props. Another time, Michaels dressed in a white outfit to contrast with The Undertaker's black. The two men were still in character, and although they were serious, there was also a strange playfulness to their one-upping; you wouldn't mistake any of their animosity as real, beyond what the script demanded.

This bled into their WrestleMania ring introductions: Michaels descended from the heavens, whereas Undertaker ascended from Hell.

Things were tense, but they weren't personal. Yet.

Credit: WWE.com

It's Hell Trying to Get to Heaven

The WrestleMania 25 match was a clinic of in-ring storytelling, and both Michaels and Undertaker played their parts beautifully.

There's a reason why WWE recently named it as the greatest WrestleMania match of all time. Of the four matches we're discussing, it is the most classical in its narrative build and presentation.

Critics tend to celebrate the near falls, like when Michaels kicked out of the Tombstone Piledriver. But those aren't what make this match endure.

On the whole, the match was a classic David vs. Goliath story; quickness and speed versus strength and endurance. Michaels had a strategy going into the match: stick and move, and cut The Undertaker down to size by targeting his legs.

Michaels dodged The Dead Man's slow haymaker swings and chopped him in response; this frustrated Undertaker, causing him to make more mistakes.

Michaels locked him in a Figure-Four Leglock to weaken his legs. Michaels pushed a camera operator in front of himself when The Undertaker tried to dive on him. Rather than trying to outpunch Undertaker, Michaels tried to win via count-out. 

None of this was "honorable," per se, but it was working.

However, every time Michaels seemed on the verge of pulling through the match, his need to be the entertaining "Showstopper" got the best of him.

He missed a moonsault to the outside of the ring when a less risky move would have accomplished the same thing. His signature skinning the cat on the ropes led to Undertaker's first Tombstone Piledriver. And the final Tombstone Piledriver came thanks to another of Michaels' moonsaults. The Undertaker anticipated it, caught Michaels and drilled him into the mat for the three-count.

Credit: WWE.com

The Obsession Consumes

Having disappeared in the aftermath of WrestleMania 25, Michaels returned to WWE several months later because of Triple H, who had finished his feud with Orton and wanted to reform DX.

What's interesting is that this is the first time that Michaels and Triple H performed in an old-timer's nostalgia act.

The crowd response was electric; they could have ridden the wheels off this gimmick straight into early retirement. But Michaels wasn't satisfied with just punching the clock.

He asked The Undertaker for another match at WrestleMania, and The Dead Man turned him down. He entered the Royal Rumble so that he could book himself in the match, and he was eliminated. And rather than accept that this part of his life was finished, Michaels made a selfish move. He goaded The Undertaker into another WrestleMania rematch by costing him the WWE World Heavyweight Championship.

And this time, the match build did not have the campy undertones of its predecessor (the Mania entrances were also free of symbolic light/dark imagery). This would be a fight that could only be won by pinfall or submission. And if Michaels lost, he would be forced to end his career, too. Now, this was personal.

Credit: WWE.com

A Career Ends

The WrestleMania 25 match was about two men reaching the ends of their primes. In their WrestleMania 26 rematch, age and physical breakdown became underlying themes.

It started when Undertaker tried to do a routine move, Old School, off the top rope. He kayfabe tweaked his knee on the landing, showing something that was once routine had become a hazard. Getting old is a humbling, sometimes humiliating experience.

And for Michaels, seeing The Undertaker tweak his knee was like sniffing blood in the water. The Phenom, so heralded as invulnerable, had a crack in his armor. And Michaels exploited it. He put Undertaker in an ankle lock; he attacked The Dead Man's knee. He even did a top-rope move right on to Undertaker's leg.

And yet, he still lost. Michaels made no blatant, hubris-driven blunders in this match; he was simply outmatched. Undertaker reversed a third Sweet Chin Music into a Choke Slam, followed by a Tombstone Piledriver.

Michaels kicked out, and this is when the narrative went meta. Undertaker, seeing Michaels rise to his feet, told him to "stay down." And Michaels defiantly used The Undertaker's taunt against him and slapped him, goading Undertaker to Tombstone him one more time.

This begging-for-the-killing-blow is a recurring motif in WWE, meant to echo Michaels' WrestleMania 24 retirement of Ric Flair. In that match, a beaten Flair begged Michaels to deliver the final blow that would send him into retirement.

After the match was over, The Undertaker broke character again by helping Michaels to his feet. Michaels appeared content that he had nothing left to prove to himself, and his obsession was quenched. For the time being.

Credit: WWE.com

The Plot Deepens

Triple H, Michaels' closest friend, picked up the mantle to beat The Streak. And this time, there was nothing classical about the booking.

Triple H's character was meaner, pettier and more monstrous than Michaels' ever was. The match at WrestleMania 27 would be No Holds Barred, allowing The Game to gain every advantage possible.

Undertaker's age had become the focal point of the narrative. He entered the ring to Johnny Cash's "Ain't No Grave," a song from Cash's posthumous album American VI. And Triple H brought up the sore topic in promos leading up to their confrontation.

The Undertaker, rather than being stoic in the face of these insults, reacted by flaring his nostrils and snarling. The Game had struck a nerve and gained a psychological advantage.

Credit: WWE.com

The Death of a Myth

The WrestleMania 27 match is the least celebrated of the four, partially because it was more like an assault than a contest. The Game pulverized his opponent with multiple chair shots, three Pedigrees and the rare, brutal chair shot to the head. He even used The Undertaker's Tombstone finisher.

When The Undertaker retaliated with an attempted Choke Slam, Triple H shook his head sadly and forced him to back down.

Triple H went outside the ring to get his Sledgehammer but had a moment of weakness, telling The Undertaker to stay down (just as Undertaker told Michaels the prior year). The Dead Man locked in Hell's Gate in what seemed a desperation move, but Triple H tapped and The Undertaker was victorious.

The Hell's Gate is always cinched in when The Undertaker is on the mat, on his back. Visually, the move looks more vulnerable than any of his other finishers. It's the only one that starts from a position of weakness rather than strength. Even in victory, The Undertaker looked weak.

And the post-match scenes were even darker. Traditionally, The Undertaker would rise to one knee and stick out his tongue as the Titantron displays The Streak intact. But this time, he was still lying down in the ring as the fireworks exploded around him. It didn't feel like a celebration at all.

The Undertaker couldn't get back to his feet and collapsed outside the ring. Eventually, he needed to be carted to the back. Triple H, meanwhile, was walking just fine despite losing a few minutes prior.

Credit: WWE.com

A Hiatus and Two Returns

This marked the end of Undertaker's weekly appearances. His next match was the following year at WrestleMania 28 against Triple H. And this time, The Undertaker had been resting for a year and was psychologically and physically ready for The Game.

Just as Undertaker did to Michaels two years prior, Triple H refused a rematch at first. And just as Triple H used Undertaker's vulnerable spot—his age—against him the prior year, Undertaker turned the tables and played into Triple H's insecurity that he lived in Michaels' shadow. And not only did Triple H accept the challenge, he demanded it be contested in Hell in a Cell, with Michaels later made a special guest referee.

There were multiple callbacks. Undertaker fought Michaels in the very first Hell in a Cell match; he pulverized Michaels, only losing because Kane hijacked the match. Being back in the cell together brought their careers full circle.

From Triple H's perspective, he wanted to overcome his Michaels insecurity by dominating where Michaels could not, and he wanted Michaels to watch while he did it. But this proved to be his downfall. By creating the Hell in a Cell stipulation, he tilted the match in Undertaker's favor by placing it on familiar ground.

Credit: WWE.com

The End of an Era

The WrestleMania 28 match resolved all of the dangling plot threads.

The Undertaker character recognized the limitations of his age. By fighting and competing on a staggered schedule, the additional rest and preparation allowed him to overcome the combined efforts of Triple H and Michaels. He looked stronger and healthier than he had since WrestleMania 25.

He also learned to play Triple H's game. He used the No Holds Barred stipulation to its full advantage, and this match's finish was an exact mirror of the WrestleMania 27's match. He beat Triple H with multiple chair shots. He caught Triple H's sledgehammer attempt and sadly shook his head.

The Triple H character was forced to accept his place in the hierarchy of greatness; he is not The Undertaker and he is not Shawn Michaels, and no amount of politicking could change that. And like Flair and Michaels before him, Triple H had one final act of defiance; he crotch-chopped and charged The Undertaker, forcing his opponent to Tombstone him one final time.

The Shawn Michaels character fell victim to old obsession; he broke his referee impartiality by superkicking The Undertaker and instantly regretted it. He spent the rest of the match with his hands clutched to his head, tormented over what he'd done. Because the truth was that he never got over his final loss, and now he may have cost Undertaker his fair chance at victory.

Thankfully for him, he was later able to count the pinfall and award The Undertaker the victory. Michaels atoned for his mistake and redeemed himself.


All three men walked arm in arm up the ramp. It was the End of an Era, and all three found some modicum of inner peace.

Michaels went back to his retirement; Undertaker continued in his role as a prestige performer; and Triple H, rather than continuing to subject himself to more physical abuse, began transitioning to a more corporate role.

Like The Undertaker, he acknowledged his aging and vulnerability. He fought less frequently, preferring instead to operate from the sidelines.

These four matches are professional wrestling at its finest, when both the verbal and nonverbal storytelling reinforce the same themes and cover the big ideas about life and personal foibles. And although wrestling only rises to these incredible moments occasionally, we were blessed to get four of them in a row to tell a single, coherent tale. Showcase of the Immortals indeed.


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