The Naismith Memorial Basketball Hall of Fame has over 450 inductees. Of that list, only five are multiple-time inductees as both players and coaches. It has to be tough to explain how to be great; you can focus on technique, teach mantras, instill accountability … but greatness? Greatness is like the E.T. Atari cartridge—everyone’s seen it, but very few people have truly possessed it. Historically, trainers and coaches in professional wrestling haven’t been very well known, but the path that leads WWE wrestlers from “Maybe?” to ’Mania now starts with possibly the most gifted gladiator ever: Shawn Michaels, the Heartbreak Kid. As his current project, NXT, starts its next chapter and one of the events he made famous is revived for today’s audience, HBK’s classic hits are helping him prepare the new generation for the big stage.
If it’s been done in WWE, there’s a good chance that Shawn Michaels (a) did it first and (b) did it better than anyone else. He’s as accomplished as they come: a four-time world champion, the first person to win the Royal Rumble as the first entrant, and a two-time inductee into the Hall of Fame for his peerless singles accolades, as well as for helping birth the Attitude Era as the first general of D-Generation X.
After spending so much of his career as WWE’s top guy, Michaels understands that sometimes you’re asked to lead, and other times you’re surprised—just to see how you’ll respond. “We didn’t tell him because we wanted it to be genuine,” Michaels admits, reflecting on the latest “first/best” idea he’s come up with. Now the head of WWE’s NXT imprint, Michaels booked Je’Von Evans, NXT’s 20-year-old highflier with a big smile and even bigger upside (lovingly referred to as “Young OG” by the WWE Universe), into a bout with 14-time world champion Randy Orton on the second episode of NXT on the CW. The catch? Evans found out about it the same way the WWE Universe did: via X during an NXT broadcast. To call it incredible would be an understatement: Orton’s debut WrestleMania match was a month and change before Evans was born.
HBK’s philosophy for his talent, as it was for his career, is that doing things outside of what’s expected is the best way to find out where you belong. Michaels’s first real test outside his comfort zone as a performer came on October 5, 1997, at Badd Blood: In Your House, where he faced the Undertaker in WWE’s first Hell in a Cell match. Hell in a Cell was designed to keep the combatants in and distractions out—a place where certain blood feuds should finish. Their bout helped signal the beginning of the broken boundaries and staggering surprises that would fuel the Attitude Era.
“I guess I always took pride in the fact that I was always the guinea pig—to see how some of these matches, these new ideas, these new, creative thoughts would work,” Michaels reflects. Over his career, Michaels has pioneered a number of WWE’s gimmick matches; he was part of its first two ladder matches (the first untelevised vs. Bret Hart, the second at WrestleMania X vs. Razor Ramon) and its first televised Iron Man match at WrestleMania XII against Hart. But while those played into his known athleticism and endurance, Hell in a Cell was there to answer two questions: How much are you willing to suffer, and are you willing to inflict that much damage on your opponent? Admittedly, being “the Showstopper” wasn’t just a promo point for Michaels; he was going to the ring, night in and night out, to reaffirm the confidence placed in him. “One of the things I think that really worked to my advantage,” Michaels shares, “is that I wasn’t bright enough to understand that maybe I shouldn’t have been putting pressure on myself for those moments.”
While most would be at least slightly apprehensive, Michaels was almost giddy when he first saw the cell. “I can remember walking into St. Louis, seeing this unbelievable structure that they had built, and I thought to myself, ‘Oh, it would look like a playground,’” Michaels remembers. “The first thing that I said is, ‘I got to get on top.’” Michaels would take a beating for most of the match, being driven into the cage face-first multiple times. But later, he would also showcase his mean streak and take the fight to the Undertaker, getting a rush of energy after taking out a cameraman whose worst crime seemed to be showing up for work that day. At the match’s apex, he’d get his initial wish, as both he and the Undertaker would scale the cell from the outside, with Michaels falling off the cage and through the ringside announcers’ table. “[The Undertaker] and I had great chemistry every time we were in the ring with each other,” Michaels says. “I feel like that’s exactly what we delivered that night, and not having any idea that it would become a regular part of something that would stand the test of time in the WWE.”
The match would retain this ruthless spirit going forward. Talents like Bayley and Sasha Banks, the Usos and the New Day, and Drew McIntyre and CM Punk wouldn’t just be competing for a spot; they’d be competing to definitively say they have what it takes to survive Hell in a Cell. “There’s something about having endured a Hell in a Cell that, from a fan standpoint, they go, like, ‘OK, he’s the real deal,’ or ‘She’s the real deal,’” Michaels explains.
Michaels’s victory in that match would solidify the stable he had been building for months: DX. Flanked by a bearded, suited-up Rick Rude, silent Superwoman Chyna, and the newly christened Triple H (Bad Blood: In Your House was the first time he was referred to by his initials, Michaels notes), Michaels would run roughshod over WWE for the next six months. He’d have to take a lengthy sabbatical to rehab a nagging back injury after WrestleMania XIV in 1998 and wouldn’t return to the ring until 2002; by that point, Triple H was a perennial world heavyweight champion. Not interested in sharing the spotlight with his former mentor, Triple H would turn on Michaels, and the two would feud over the next few years. In 2004, Michaels would main-event another Bad Blood pay-per-view in a Hell in a Cell match, paralleling the Undertaker’s spot as the man against an army, with Triple H now solidified as the leader of his own unit, Evolution. “There’s a bond there, but there’s also been this rift,” Michaels explains. As a result, that match had a lot of different dynamics compared to the bout with the Undertaker, Michaels says. After almost 50 grueling minutes, Triple H would end up winning the match.
For Michaels, the biggest difference between the matches was that by the second one, he had gained a better understanding of himself and what he was capable of presenting to the crowd, emotionally and physically. You could hear the coaching wheels turning in his head as he explained the changes that occurred between runs. “Well, the whole second run was satisfying in a lot of ways. But in particular for this match, I think, again, you’re talking about as you get older, you get wiser,” Michaels says.
After his official in-ring retirement in 2010, Michaels would make rare appearances on WWE television. As Triple H transitioned to WWE’s front office, he and Michaels teamed up once more, with Michaels working under Triple H as a producer for NXT. In 2022, Michaels became head of the NXT brand, being named the senior vice president of talent development creative. Earlier in his career, he cofounded and coached at his own school, the Texas Wrestling Academy, but being responsible for all aspects of a talent’s professional upbringing was a different beast. One thing that eased the transition was the level of talent entering the WWE Performance Center in Orlando. The roster had many former Division I athletes who were involved in football, soccer, and/or gymnastics and were attracted to the dream of building on what they’d already accomplished in a new arena. “We started recruiting from those universities, and so many of those athletes, whether it be a Tank Ledger—NXT’s first NIL guy—Oba Femi, Trick Williams, [or] Kelani Jordan, [they] understand that they can do this, so they can fall in love with this,” Michaels explains.
It seems like quite the role reversal for wrestling’s most famous heartbreaker to be working to build a program of passionate competitors, but his focus and attention to detail shine through every week on NXT. It also helps that as they learn the ropes, Michaels is picking up brand-new ideas. “Everybody thinks they know it all in this business. I can tell you, I’m 59 years old. I’ve been doing this for 40 years, and I learn stuff every day. And if you’re not learning, you’re not growing.”
NXT’s largest event to date, Stand & Deliver in April 2024, featured the intense feud between Trick Williams and Carmelo Hayes in the main event. Their story line mirrored Michaels’s Two Dudes With Attitudes run with Diesel, as the established star (Hayes) felt threatened by the rising popularity of his heavy (Williams). There was no ambiguity; Hayes made it clear he didn’t think Williams was on his level, only to be proved wrong in front of tens of thousands at the Wells Fargo Center. Some of the most memorable moments of their partnership—and feud—would take place at NXT’s resident barbershop, a clear nod to Michaels breaking out on his own more than 30 years prior. The physical portion of the homage extended to the women on NXT as well, with Jacy Jayne kicking ex-partner Gigi Dolin through a door, similar to how Michaels superkicked Marty Jannetty before throwing him through that barbershop window. Even the clashes in the show’s parking lot, where the violence seems to intensify, pay homage to the backstage altercations that DX was known for.
“I don’t know that there’s anything in our line of work creatively that … hasn’t been done at one point or another,” Michaels admits. “And I don’t think it hurts to have people knowing that I’m the guy behind the scenes, and there’s a little wink and a nod maybe to that.”
During a week in which two of the most definitive moments of his career are either launching (NXT on the CW) or being revisited (this Saturday’s Bad Blood premium live event in Atlanta), Michaels seems to be focused on elevating the business that’s meant so much to him. Hell in a Cell, as always, will provide brutal yet enduring moments, and Saturday’s match between Punk and McIntyre looks to further elevate their storied rivalry. But Michaels’s legacy is now tied to the future superstars he’s trying to mold in the hope that they can surpass what he accomplished during his in-ring career. But how does the very best give even more back to the game after all the blood he’s shed, all the steel he’s crashed into?
“I started out as a coach,” Michaels says. But he realized that it was more difficult for him to teach because so much of his pro wrestling ability came to him naturally: “Natural gifts can’t be taught,” he says. Michaels takes his role in WWE seriously, understanding that the onus is on him to figure out how to verbalize the magic that made him a two-time Hall of Famer for the next generation of WWE superstars.
Michaels admits that while helping the competitors in NXT achieve their dreams can be very challenging, he appreciates that going from showstopper to superstar molder came naturally to him. “I’m so fortunate that it’s in me. I love doing it. I get to go every day, and I don’t feel like I’ve worked a day in my life.”
Cameron Hawkins writes about pro wrestling, Blade II, and obscure ’90s sitcoms for Yahoo Sports’ Uncrowned and Complex. You can follow him on Twitter at @CeeHawk.
