Shawn Michaels Regrets Stepping Into The Ring For This High-Profile Storyline

WWE Hall of Famer Shawn Michaels has one of the most decorated and celebrated careers in the history of WWE. "The Heartbreak Kid" is cited by many fans, as well as some of his peers, as the greatest WWE Superstar ever, and ended up having not one, but two iconic spells with the company. After The Rockers disbanded, Michaels flew solo right around the time when WWE needed to shift away from larger athletes due to the well-documented steroid trial, leading to him reaping the benefits and becoming the company's top star throughout most of the 1990s. After a four-year stint away from the ring, where he recovered from a back injury and dedicated his life to religion, he returned in 2002 and had another eight years in the spotlight.

Cast your minds back to the beginning of 2010. Michaels is still lingering around the main event scene in WWE, but has become burdened with the fact that he came within millimeters of ending The Undertaker's legendary WrestleMania winning streak at WrestleMania 25. He put the call out for a rematch, to which "The Deadman" declined, meaning that Michaels would have to take matters into his own hands. He failed to win the 2010 Royal Rumble match to earn a shot at Taker's World Heavyweight Championship, so he decided to cost him the title at Elimination Chamber 2010, leaving "The Deadman" with no choice but to finally accept HBK's challenge, but only if Michaels promised to retire if he lost at WrestleMania 26.

Unlike WrestleMania 25, The Undertaker's match with Shawn Michaels main evented WrestleMania 26, and it was another classic bout between the two men, but despite giving everything he had, Michaels was left looking at the lights in Phoenix. He lost the match and was forced to retire, which ended up being one of the few wrestling retirements that actually stuck, making "The Heartbreak Kid's" career stand above many of his peers in the process...until 2018.

After mocking the idea of ever coming out of retirement and tarnishing his legacy, Shawn Michaels came out of retirement and tarnished his legacy (to an extent). 

In the build-up to the 2018 WWE Crown Jewel pay-per-view in Saudi Arabia, it was announced that Michaels would be reuniting with Triple H to take on Kane and the man who retired Michaels in 2010, The Undertaker. This match came during a time when the WWE shows in Saudi Arabia were more glorified house shows than canon events, and a way for the people of Saudi Arabia, but more specifically the Saudi Royal Family, to see some of the biggest names in wrestling. To put into context what type of matches and wrestlers the Saudi Prince wanted on the shows, both Yokozuna and The Ultimate Warrior were requested for the Greatest Royal Rumble event in April 2018, despite both men being dead for several years.

Having said all of that, D-Generation X taking on The Brothers of Destruction sounds like a dream match on paper, and it should have stayed a dream as the bout ended up being a disaster. Kane's mask fell off during the match, Triple H suffered a torn pectoral muscle, and The Undertaker was left still wanting that ultimate retirement match that he had been craving. It was because "The Deadman" wanted the match to be good that Michaels initially regretted taking part in it, stating in a 2021 interview with the New York Post that had he known The Undertaker was looking for this to be his swan song, he would have given everything he had left to make it as good as possible.

In the years since that interview, Michaels has actually come around on the match, stating in an appearance on the "Insight" podcast that it felt like more of a send-off for him than a retirement match, and that it felt like a guy just hanging out with his friends.