The Undertaker and Shawn Michaels are widely considered to be two of the greatest WWE superstars of all time, with their pair of WrestleMania matches generally sitting atop of any list that revolves around best WrestleMania matches, best WWE matches, or even best matches, period. They were also involved in the first-ever Hell in a Cell match back in October 1997. However, another Undertaker vs. Michaels match, just a few months after Badd Blood, almost ended the career of “The Heartbreak Kid.”
The 1998 pay-per-view calendar kicked off with the Royal Rumble, and Michaels defended the WWE Championship against “The Deadman” in a match that Undertaker knew very well — a casket match. Up to that point, Undertaker had been in more casket matches than anyone else in WWE, but Michaels got the win and retained the WWE Championship. That wasn’t the biggest talking point of the match, however.
During the bout, Undertaker delivered a back body drop on Michaels from the ring to the outside, with Michaels’ lower back clipping the casket that was situated at ringside. The move seemed insignificant at the time, but it would ultimately led to Michaels stepping away from wrestling for more than four years. Hitting the casket caused Michaels to herniate two discs in his back, while also crushing a third, and despite finishing the match, doctors at the time told him that he would never wrestle again.
Michaels soldiered on and dropped the WWE Championship to “Stone Cold” Steve Austin at WrestleMania XIV, though with hindsight, Michaels now claims he shouldn’t have wrestled the match, as he was one misstep away from total catastrophe. “The Heartbreak Kid” didn’t have any ill will towards Undertaker for the move, as he admitted that his back was already destroyed and the 1998 Royal Rumble was simply the straw that (literally) broke it. Fortunately for Michaels, the injury turned out to be career-halting rather than career-ending, as he would return at WWE SummerSlam 2002 and author a new chapter of his career that was arguably better than the first. Ironically, Michaels’ WWE career would be ended by none other than The Undertaker himself at WrestleMania XXVI (Michaels himself says his actual last match doesn’t count).