In the history of boxing, Mike Tyson is one of those prolific names who has made a meaningful impact on the heavyweight division by showcasing his exceptional skills. Despite his short prime and controversial career, Iron Mike has always been a fan favorite who has earned a brutal image for his actions.

Well, when we look at the best moments of Tyson’s career, it is filled with moments that are not the best. One such moment was when he was a special enforcer during Stone Cold Steve Austin vs. Shawn Michaels at WrestleMania 14, which commenced the Attitude Era.
However, the beginning was marked by a controversy that had left Shawn Michaels fuming at the acclaimed heavyweight boxer for creating a WrestleMania moment that came at the cost of his reputation.
WrestleMania 14: The time when Mike Tyson knocked out Shawn Michaels cold
Anyone who grew up watching WWE in the late 90s would remember how they were glued to their TV screens watching the most popular period of sports entertainment, the Attitude Era. This period featured some of the hottest wrestling names, like The Rock, The Undertaker, Kurt Angle, and so many more, who elevated the status of the game to a whole other level.

While this era has been hailed as the greatest period of World Wrestling Entertainment, then WWF, it commenced on a controversial note. It comes as no surprise that Shawn Michaels is one of the biggest names in the wrestling company, who has proved why he’s one of the greats of this profession. However, there’s one moment in his career that irritates him even today.
It’s none other than the match at WrestleMania 14 against Steve Austin, with Mike Tyson as the special ring enforcer. Michaels was already suffering from a back injury that made things already too difficult for him, which he picked up at the Royal Rumble. The presence of three combustible elements was already a bad idea.

To make things worse, Tyson knocked out the Heartbreak Kid after his defeat at the hands of Austin. When he looks back at the moment, he still feels bitter, as Mike Tyson ruined his final moment as a superstar at that time. A clip from the now-deleted show, Biography: WWE Legends, Season 4 Episode 106, was shared on X, Triple H shared how the HBK was already “p**sed” about the match and he tried to keep it together. He said,
He was p**sed. He wasn’t about to talk to Steve about this match. I helped them put it together by going from room to room.
Michaels recalled how the match was already difficult and being in that much pain wasn’t making things easier for him; the video showcased glimpses from the match. While losing his title wasn’t enough, he lost his remaining dignity in the post-match, as Tyson hit him with a right hook, leaving him knocked out cold for quite some time, and then covered his face with an ‘Austin 3:16’ T-shirt.
Even Steve Austin mentioned how Iron Mike added “insult to the injury, and that’s what rubbing salt to the wound” looks like. The 16-time WWE Champion was outraged and decided to storm the press conference, but was stopped by Shane McMahon before chaos took place.
Triple H recalled how Michaels storming at the press conference was unscripted, and he was genuinely unhappy with Tyson for ruining his moment. Well, for better or for worse, he was stopped because messing with Iron Mike should be the last thing on anyone’s list, and that too for genuine reasons.
The WWE Universe reacts to Mike Tyson’s right hook to Shawn Michaels
Following the chaos that took place at the main event of WrestleMania 14, the fans took to social media, reacting to how Michaels could not do anything that happened at the show of shows. The fans offered a grounded perspective, stating how messing with Tyson was a bad idea and that it would have ended up with Shawn Michaels getting knocked out again.

However, some were glad with how the HBK taking his time off from the squared circle made him return as a changed man, making him a beloved figure of the sport. The fans commented,
It was a really good match and now I understand why both men don’t like it though. I’m so thankful we got to see a healthy Shawn, off of the drugs when he returned in 2002 and it’s even better to see him giving back to the business running NXT
— Josh Johnson (@Josh_A_J) March 16, 2025
The funniest part of all of this is Shawn being pissed at Tyson for the shirt thing, but realistically what would he have done backstage…you gonna fight Tyson? That’s a lose lose situation😂
— Mikey (@TheMikeSanchez_) March 16, 2025
Austin and HBK could have had an all time great match in like 97 before the respective back and neck injuries.
— Undead Sir Karl (@GoldBoxRPGGuy) March 16, 2025
I like how present day shawn admits he was being a massive prick and probably deserved the shirt thing while austin said he completely understands shawn being mad. Extreme accountability from both men
— Anthony (@anthony_sc37875) March 16, 2025
This was his karma for sure
— Million Dollar Will (@1804Show) March 16, 2025
90’s Shawn wasn’t a good person, good thing he turned to god, but from what I’ve heard, he was just a terrible human being, as great as he is, he should’ve been even greater if it wasn’t for his own demons
— Brian (@Bfish3422) March 16, 2025
Nevertheless, the member of D-Generation X would never be delighted to look back at the moment of his career, and how, despite giving it all, it left a sour taste in his mouth about the entire incident.
WrestleMania 41 will be a two-night event taking place on Saturday, April 19, and Sunday, April 20, 2025.
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