The Real Reason Shawn Michaels Retired From Wrestling

When you watch pro wrestling as a kid, every performer seems immortal, especially Hulk Hogan, who started being marketed as "The Immortal Hulk Hogan" in the 1980s after Marvel smashed Hulk financially for calling himself "Incredible," per Cinema Blend. Of course, his immortality temporarily died at Survivor Series in 1991, when the Undertaker delivered a Tombstone piledriver to Hogan and won his first world championship. That year also marked the start of the Undertaker's undefeated streak at WrestleMania, per Bleacher Report. No one realized it at the time, but that streak would eventually bring an end to Shawn Michaels' career.

Though known as the "Heartbreak Kid," Michaels had a habit of stealing hearts along with the show. Whether it was his iconic Iron Man match with Bret Hart, his classic matches against Kurt Angle, or his ridiculous DX antics, his performances were as sweet as his Chin Music. And contrary to his theme music, Michaels wasn't just a sexy boy; he was also a Playgirl model. More importantly, he was "Mr. WrestleMania," a man you always believed would outshine the spotlight on the brightest stage of them all. So when Michaels vowed to retire if he couldn't end the Undertaker's streak at WrestleMania XXVI, diehard fans hoping that Michaels' career would live forever had to believe the Dead Man's undefeated streak would die.

The streak did die, but not that night. That night, the Heartbreak Kid truly lived up to his name, shattering the hearts of longtime devotees in what Sportskeeda describes as the "greatest" story line in WWE history and what the WWE describes as possibly "the greatest collective loss in WWE history." Since, as this intro illustrated, Shawn Michaels is immortal like the rest of your favorite wrestlers (wait, was that the point of this intro?), you might ask, "Why couldn't his career be immortal, too?"

The WrestleMania XXVI showdown between the Heartbreak Kid and the Undertaker felt like the physical equivalent of a love letter to fans. It had passion and poetry of motion. It had the Undertaker's top-rope funambulism and Michaels moonsaulting from the top rope to send the Undertaker through a table. It had thrilling near-falls and brilliant in-ring psychology. Bleacher Report contributor Jon Alba said of that epic encounter, "Being 100% unbiased and detached from the situation, this may have been the greatest match I have ever seen. Ever."

For a moment, it seemed like Michaels would win. In the final moments of the match, Michaels delivered his trademark superkick, Sweet Chin Music, and the WrestleMania crowd roared with the visceral joy of a child who believed they'd never have to grow up. But the Undertaker kicked out at two. Michaels tuned up the band again, but just before it seemed like they reached the crescendo, a chokeslam from the Dead Man silenced Michaels temporarily. Yet the Tombstone piledriver that followed failed to bury his career.

Nevertheless, the end was coming. The finality was written across Michael's face. The Undertaker hesitated to strike the final death knell and shouted, "Stay down!" But Michaels taunted the Undertaker with his own throat cut motion, rose to his feet, and slapped the Dead Man across the face with every ounce of heart he had before the Undertaker sealed his fate with one last furious Tombstone. Somehow he and the Undertaker simultaneously gave fans everything they could hope for in a match and the one thing the dreaded the most: the end of the legendary Heartbreak Kid's career.

On the Monday Night Raw following WrestleMania XXVI, the Heartbreak Kid Shawn Michaels looked every bit as heartbroken as the fans awaiting his farewell speech. The ring looked lonely even though Michaels was standing in it, and the fans looked like a mass of cheering tear drops. In that sweetly awful goodbye, Michaels uttered these once seemingly unspeakable words: "At 23 I started coming in to each and every one of your homes every week. And the idea of now being 44 and not coming into your homes on that TV set every week is gonna be ... is gonna be a little tough to get used to." As he thanked those who did right by owning up to wronging others in the past, fans were a mix of appreciation and denial. As Bleacher Report recounts, the crowd shouted, "Thank you Shawn," "One more match," Please don't go," and "HBK." Their chants lacked the athletic poetry of the previous night's match, but they brimmed with the raw emotion of a true goodbye. For many who grew up watching him and tried vicariously through his character to feel larger than life, it wasn't just goodbye to a career; it was a hello to the passage of time, a moment when one had to accept that Michaels was awakening from his boyhood dream, and fans were letting go of a slice of their childhood.

In the years that followed people would ask pro wrestling's beloved showstopper to restart the show. But as Michaels matter-of-factly explained in an interview, "I wouldn't have retired unless I was ready to walk away. I'm flattered that every year when WrestleMania comes up people talk about me coming back, but I enjoy my time with my family, I enjoy watching WrestleMania and I also enjoy watching WWE move into the future."

Michaels returned to the ring in 2018 to compete at WWE Crown Jewel but didn't see it as exiting retirement. "To me it wasn't coming back as the Heartbreak Kid," he said. He considered the Saudia Arabia pay-per-view more of "a glorified house show, a live event" but clarified, "I don't mean that to be intellectually insulting to the wrestling fan, but in my mind, it was just so not the same." And it hasn't been the same without him.