WWE Retrospective : End of an Era

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Article written by Dylan McGuire Devine (11/26/21)

The end of an era match/storyline is one of the most iconic and well known storylines in wrestling history. The storyline goes back a bit further back then most people know and in this article I am going to go through all the details dating back to 2009.

Michaels and Taker’s brief interactions (2007 and 2008)

Undertaker and HBK had faced off on multiple different occasions in the attitude era, but since Michaels returned to the WWE in 2002 the two only had two real interactions on TV. Both interactions were brief as both occurred in the 2007 and 2008 Royal Rumble. After two years of teases in the Rumble match, Taker and HBK were officially set to face of at Wrestlemania 25.

Wrestlemania 25

Shawn Michaels vs. The Undertaker at Wrestlemania 25 is the greatest Wrestlemania match of all time. The chemistry these two had and the story they told in the ring was nothing short of amazing and the match still hold up 12 years later. The Undertaker defeated Michaels which kept his Wrestlemania streak alive.


After Michaels was defeated by The Undertaker at the grandest stage of them all in 2009, he wanted one more shot at defeating the streak. The Undertaker ended up becoming World Heavyweight Champion in 2010 which meant the only way HBK would get his match with Taker was if he were to win the Royal Rumble. Michaels failed to win the Royal Rumble which meant he wouldn’t be able to face Taker at Wrestlemania. HBK went on to challenge Taker multiple times on Monday Night Raw but Taker consistently refused a rematch. We’re now around the time of the annual Elimination Chamber PPV. Taker was set to defend his World Title in the Elimination Chamber match against Chris Jericho, John Morrison, CM Punk, R-Truth, and Rey Mysterio. It looked like Taker was going to retain as him and Chris Jericho were the final two, but out of nowhere Shawn Michaels popped out from beneath the chamber and superkicked Taker. This led to Jericho pinning Taker and Jericho was now the new World Champion. This was HBK’s way of provoking Taker to get his match at Wrestlemania. Taker was LIVID with Michaels and finally accepted Michaels challenge for a rematch. The match was now officially set for Wrestlemania 26.

Streak vs. Career (Wrestlemania 26)

Taker finally accepted HBK’s challenge for a rematch, but under one condition. HBK had to agree to put his career on the line against Taker. Which meant if he lost, he would have to retire. Michaels agreed to putting his career on the line famously saying “if I can’t beat you at Wrestlemania, I have no career.” The two went on to put on yet again another all time classic Wrestlemania match which is still regarded as one of the best mania matches of all-time. Taker defeated HBK which meant Michaels now had to retire. It was a storybook ending for Michaels having his last match be one of the greatest ever against his most famous opponent.

The 2011 return of The Undertaker

After his Wrestlemania 26 match with HBK, Taker took some time off from wrestling. In early 2011 vignettes began airing teasing his return. Fans weren’t 110% sure it was Taker, but as more and more vignettes released it became apparent that we would be seeing the return of the deadman. Taker made his return on the February 21st edition of Monday Night Raw. Taker didn’t even get the chance to speak as Triple H also made his long awaited return and interrupted Taker’s big moment. The two didn’t even have to exchange words. They both just back and forth stared at the Wrestlemania 27 sign in the arena and we all knew what that meant. The segment ended with both guys doing their signature taunts towards each other and it was on. The match between Triple H and The Undertaker was officially set for Wrestlemania 27.

The buildup to Wrestlemania 27

The buildup to the Wrestlemania 27 match between Taker and Triple H was relatively simple. Triple H was attempting to do what his best friend couldn’t do. He wanted to end the streak. He cut a promo on Taker basically telling him that he didn’t think Taker was on the same level he used to be on. Triple H wanted to be the 1 in 18-1. Wrestlemania 27 is arguably the worst Mania ever, but the match between Taker and Triple H was without a doubt the highlight of the show. Triple H fell short which meant The Undertaker’s streak was now at 19-0.

The Journey to Wrestlemania 28

After Wrestlemania 27, Undertaker disappeared from WWE TV until January of 2012. Taker returned on the January 30th edition of Monday Night Raw and came out to the ring and challenged Triple H to a match at Wrestlemania 28. It was very similar to how Triple H challenged Taker in 2011 with both men not saying anything but just looking at the mania sign. Except this time Triple H declined Undertaker’s challenge. Triple H went on to explain why he declined the challenge. He said that out of respect for Taker, he wouldn’t face him again at Wrestlemania because he knows what he has to do to beat him. He believes he has to finish The Undertaker and feels like Taker wants him to defeat him, but Triple H doesn’t want to.

Over the next few weeks there were multiple segments between Triple H and Taker and even one where HBK made his return. The final segment before Triple H finally agreed to face The Undertaker is one of the best segments/promos ever. Taker tells Triple H that him, Shawn, and Taker are the end of an era. The last of their kind. He insults and provokes Triple H by telling him he was always second best behind HBK. He tells Triple H that he is too worried that he can’t do what his best friend couldn’t do and defeat the streak. This sets Triple H off and he goes off on Taker saying he can do what Shawn couldn’t do and says he is more certain than ever before that he can finish The Undertaker at Wrestlemania. He then agreed to the match, but under one condition. Hell in a cell. Undertaker went on to accept the match and Shawn Michaels went on to become special guest referee for the match which made things even more interesting. Could HBK stay unbiased and call the match fair and square?

The end of an era

Wrestlemania 28 took place in Miami, Florida. The crowd was ALL IN for this match. Taker, Triple H, and HBK all got huge reactions during their entrances and the crowd was pumped. The hell in a cell structure dropped to a bad ass song and everyone instantly knew this was going to be a classic. These two guys beat the hell out of each other. There was a lot of back and forth arguing between HBK and both Taker and Triple H. Shawn kept intervening during certain big moments which would aggravate Taker and Triple H depending on who was on top at the moment. This match had some of the most insane two counts in the history of wrestling. On top of that, it had arguably the craziest false finish in wrestling history. Taker went for his iconic tombestone piledriver on Triple H, but HHH reversed it which sent Undertaker into a superkick from Michaels and then a pedigree from Triple H. EVERYONE thought this was it. The streak was finally going to be put to an end. But Undertaker wasn’t going to go out like that. He kicked out just before the three count and the crowd went bonkers.

This turned the tide of the match completely and due to Triple H arguing with HBK, Taker got up and gained some momentum. It was back and forth for a few minutes but Taker ultimately went on to finish the job. Triple H gave Taker one last DX crotch chop which led to a sledgehammer to the head from Taker then his signature tombstone piledriver. HBK counted the pin one, two, three. The Undertaker was now 20-0 at Wrestlemania. All three men in the ring were distraught. HBK was emotional while both Taker and Triple H were still down. Michaels ended up giving Taker a hand in getting up and then goes over to his best friend, Triple H to do the same. The crowd gave a standing ovation as three of the greatest and most iconic wrestlers ever walked up the stage together in arms. All three guys turned around at the top of the stage, took in the moment they were in, then embraced each other which led to one of the most iconic moments in wrestling history. This was the last time we would be seeing these three men in the same ring together (ignoring the disgraceful match at crown jewel in 2018 between DX and the Brothers of Destruction).

There will never be a storyline as storied and as iconic as the end of an era storyline which had a four year span. Three of the greatest wrestlers of all-time and four of the greatest Wrestlemania matches ever. It doesn’t get any more iconic than that.

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