In the late 90s, the tide started to turn in the Monday Night Wars when WWE made a big investment by acquiring boxing legend Iron Mike Tyson. Tyson became the special guest enforcer for the WWE Championship match between champion Shawn Michaels and challenger Stone Cold Steve Austin at WrestleMania 14. Tyson’s insertion into the storyline was a turning point that eventually led to WWE winning the Monday Night Wars.

On the latest episode of the Grilling JR Podcast, Jim Ross talked about how monumental the Tyson appearances ended up becoming for the growth of the WWE. Ross mentioned how he also made sure on commentary to cement that the WWE guy was the bigger star.

“It was a big moment, no doubt,” Ross said. “It made a lot of headlines and put Austin in the spotlight he needed to be, very defiant, very anti-corporate stuff. Vince’s look on his face was brilliant because he had dollar signs in his eyes looking at Tyson and Austin and Tyson being a part of the brand and Austin trying to screw it up.

“It was a big night for us. I made sure [on commentary] when I said Austin and Tyson, I didn’t say Tyson and Austin, because I wanted to give our guy Stone Cold the top billing.”

It’s been reported over the years that Tyson was offered $3.5 million dollars for the gig. Ross mentioned how during those appearances they made sure to keep Tyson as happy as possible and provide him with anything he wanted. He also said that Shane McMahon was cast with taking care of all of Tyson’s needs.

“Shane McMahon had a lot to do with that,” Ross said. “He became Tyson’s concierge, whatever Mike needed [Shane got him]. I think during his time, Tyson wanted a motorcycle, I have no idea why, and Shane bought him a motorcycle. They tried to appease him, it’s like recruiting a college football player or basketball play.

“The WWE tried to take care of Mike at every turn of the road and Mike needed money at that point in time. The McMahon family took care of him and it worked out. It was a good investment quite frankly because it paid off at the end of the day.”

If you use any of the quotes in this article, please credit Grilling JR Podcast with a h/t to Wrestling Inc. for the transcription.