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.