Boxing legend Mike Tyson didn’t just pack a punch in the boxing world, he has also left his mark in the world of professional wrestling.

“Iron” Mike will be presenting AEW’s newly-minted TNT Championship to either Cody Rhodes or Lance Archer this Saturday at Double or Nothing but his connection to the squared circle goes all the back to 22 years ago in the WWE.

Tyson’s first appearance was as a supporting character in the Stone Cold Steve Austin versus Shawn Michaels match for the WWF World Heavyweight Championship at WrestleMania 14. Although he would be the designated ring enforcer for that main event match, Tyson would play heavily into the angle as it evolved.

On the January 19, 1998, edition of Monday Night Raw, Vince McMahon had a special announcement to make. Mike Tyson was introduced by McMahon and came down to the ring to shake McMahon’s hand.

AEW’s Chris Jericho knows what it is like to be on Mike Tyson’s bad side. Photo: WWE.

“At WrestleMania, in this very ring, ‘Iron’ Mike Tyson will…” was all McMahon could say before “Stone Cold” Steve Austin’s music hit.

Austin strode around the ring as officials tried to rein the Rattlesnake in.

McMahon demanded to know why Austin had come down to the ring. Austin replied that Tyson making friends with everyone in the back and shaking their hands made him sick.

Tyson offered his hand to Stone Cold.

“I am NOT going to shake your damn hand because I am NOT out here to make friends with you. I respect what you have done in the boxing world but Jesus Christ son, when you step in this ring you are messing with Stone Cold Steve Austin and that is something you don’t do!” bellowed Austin pointing his finger in Tyson’s face right before saying he wanted a “piece of Mike Tyson’s ass.”

Austin flipped off Tyson. Tyson shoved Austin. A brawl broke out with Tyson and Austin wanting to knock each other’s lights out.

It was thought by many fans and media at the time that Tyson would fight Austin at WrestleMania but that wasn’t to be the case. At a subsequent press conference McMahon announced that Tyson would be the special enforcer in the WrestleMania main event.

Tyson would return to Monday Night Raw on March 2nd, this time with the WWE World Heavyweight Champion Shawn Michaels and D-Generation X.

“Who do you believe will win the match?” McMahon asked Tyson about the WrestleMania main event just as D-Generation X’s music played. Officials tried to stop HHH, Shawn Michaels and Chyna from entering the ring.

“We aren’t out here to disrespect you like ‘Stone Cold’ Steve Austin did. That is not D-Generation X’s style,” said Michaels before calling Tyson out.

“If you want to do it, let’s do it right now!” Tyson fired back.

Instead of brawling though, Michael ripped off Tyson’s WWE shirt to reveal a D-Generation X shirt underneath.

“Don’t tell me Mike Tyson joined D-Generation X?” gasped a befuddle Jim Ross.

D-Generation X hugged Tyson as he crotch-chopped the audience and Vince McMahon himself.

With Tyson’s allegiances in question, “The Baddest Man on the Planet” did enforce the rules in the WrestleMania 14 main event. He even tossed Austin back into the ring and with referee Mike Chioda knocked unconscious Tyson would deliver a quick three count declaring Austin the new champion. Tyson would tear off his D-Generation X shirt. He wore a Stone Cold shirt underneath. Shawn Michaels confronted Tyson about the quick count. Tyson knocked him out with a haymaker.

Tyson would return to the WWE to host Raw on January 11, 2010. Tyson would be interrupted by the WWE Champion at the time, Sheamus. Randy Orton, John Cena, Kofi Kingston would come to the ring each claiming to be the number one contender to Sheamus’ title. Tyson would sanction a triple threat match to determine Sheamus’ challenger at the Royal Rumble. That would end up being Randy Orton.

Tyson would agree to team up with Chris Jericho to face D-Generation X that night. DX-wannabe Hornswoggle sped into the ring in boxing attire during the match demanding to fight Tyson. A snickering Tyson tagged in Jericho. While Jericho laid the bad-mouth on DX, Tyson took off his shirt which covered a DX shirt. Tyson knocked out a shocked Jericho so that Shawn Michaels could pin him.

Then there was the appearance that never happened that predated all of the above. In February 1990, Tyson was set to be the guest referee for a Hulk Hogan versus “Macho Man” Randy Savage bout, but then the unthinkable happened. On February 11, 1990, James “Buster” Douglas upset the undefeated Tyson in Tokyo to win the undisputed heavyweight title. WWF quickly changed its plans and invited Douglas to referee instead, and Buster knocked out Macho Man.

Tyson was later inducted into the WWE Hall of Fame in 2012.

“I am honored to be inducted into the WWE Hall of Fame,” Tyson said at the time. “I was the youngest heavyweight champion of all time but the most fun I ever had in the ring was with WWE.”