The Baddest Angle on the Planet: Iron Mike Tyson in the WWF

Brian Damage

‘Iron’ Mike Tyson was one of the fastest rising stars in the professional boxing industry. At the same time, Tyson was also an extremely polarizing figure. He was convicted of rape in 1992 and spent three years in prison for his crime. Despite that, Tyson was still perhaps one of the most marketable boxers in the business…probably only behind Oscar De La Hoya. Iron Mike was a commodity, and people were willing to pay good money to see him. 

It only seemed natural that the pro wrestling world wanted to capitalize on Tyson’s celebrity. With Tyson being a fan of pro wrestling fan himself, that made him even more appealing to promoters. Enter Eric Bischoff who was in the middle of a wrestling war with Vince McMahon and the WWF. Both companies were pulling out all the big matches and surprises to have bragging rights over the other. Bischoff was the first to contact the Mike Tyson camp and negotiate a deal for the so called “Baddest Man on the Planet” to appear on WCW’s flagship show Monday Nitro.

It seemed to be a done deal. Nitro was being held at the MGM Grand Arena in Las Vegas, Nevada… the same venue where Mike Tyson’s big fight was happening two nights prior. While it was unclear what role Tyson would have on Nitro, it never took place. That’s because his big fight ended in a great deal of controversy. That was the fight where Tyson bit off the ear of his opponent Evander Holyfield in a page taken right out of pro wrestling’s script. The ear biting incident made worldwide headlines and none of it was positive. The agreed upon appearance involving Tyson on Monday Nitro was scrapped by Turner executives fearful of getting nasty publicity.

Vince McMahon saw the incident a lot differently than Bischoff and WCW and six months later…was negotiating his own deal to get the disgraced boxer into the WWF.  The WWF was changing their format from family friendly to more adult oriented. This, as we know, was the Attitude Era for the company. In January of 1998, the WWF let word get out that the company were in talks with boxing promoter Don King for Tyson to appear at Wrestlemania 14. It was announced later that month that a deal had been signed between the two parties. The plan was always going to be Mike Tyson as a “ringside enforcer” aka special guest referee…but that didn’t stop McMahon from teasing something bigger. 

On January 19th, 1998, Vince McMahon introduced Tyson to WWF fans on Monday Night Raw. His appearance was then interrupted by the company’s emerging top star Stone Cold Steve Austin. Austin began running down Tyson and that led Austin giving Tyson the middle finger which led Tyson to shove Austin and a pull apart between the two men. Austin revealed on his podcast that McMahon asked Austin to throw some real punches at Tyson to which Austin looked at Vince as if he were crazy or high. Austin also recalled that after Tyson shoved him, a number of $100 dollar bills fell out of Tyson’s pockets and his entourage who were supposed to be in the angle and separate the two men, were instead reaching on the mat to pick up the loose money. Austin recalled, “I’m over there kicking and scratching trying to get that son of a bitch, and I’ll tell you what, if they had put Mike Tyson vs Stone Cold on Pay Per View, I don’t think that anybody would’ve beat it to this day.”

The physical confrontation led to a ton of mainstream publicity for the WWF. It was mostly negative feeling that Tyson had fallen so low that he had to resort to professional wrestling as a side job. Regardless, it was exactly what Vince McMahon had wanted. News outlets began speculating that the main event of Wrestlemania was going to be a one-on-one match between Stone Cold Steve Austin versus Iron Mike Tyson. Fans all over the world were buzzing over that possibility. The thing was that was never the plan. First off, Tyson’s camp demanded that Mike Tyson be presented as a well liked babyface to help him get reinstated in boxing. Wrestling Austin was not going to help that from happening. Secondly, the plan for the Wrestlemania 14 main event was already thought out months in advance and Vince was not a fan of suddenly changing course. Granted, he didn’t oppose the idea, it just didn’t help him in the long run of storytelling. A press conference was announced and it was there where the rumors of Austin vs Tyson were squashed and Tyson as expected, was made a special ringside enforcer in the main event between Austin and WWF champion the Heartbreak Kid Shawn Michaels.

Tyson had agreed to work several dates to help promote his appearance at Wrestlemania…but ended up no showing the first appearance before that press conference. That Raw was held in Indianapolis, Indiana…the place where Tyson’s rape trial took place. Tyson refused to appear and no showed, but it was understood and no harm came from it. The big swerve from this angle came when Shawn Michaels confronted Tyson and instead of punches being thrown, ripped off his shirt to reveal a Degeneration X shirt underneath. This made fans believe that Tyson had aligned with the heel Shawn Michaels and DX and added a new wrinkle into the storyline.

According to Bruce Prichard, Shawn Michaels was not very happy about the angle involving Tyson. Michaels knew this was perhaps the final match of his career due to the severity of his back injury and felt that all the talk going into that main event match was all about Mike Tyson and Stone Cold Steve Austin. Shawn Michaels was nothing more than an afterthought and was felt that he was in the WWF’s rearview mirror. Prichard admittedly did not disagree with Shawn’s feelings, as the company was in fact moving forward without the Heartbreak Kid in its future plans.

During the lead up to Wrestlemania, Vince wanted to ensure that not only the temperamental Tyson remain happy but stay out of any trouble. To do this, McMahon assigned his own son Shane to look after Iron Mike. Shane McMahon essentially became a babysitter to the baddest man on the planet. Shane went everywhere Mike wanted to go and even reportedly bought Tyson a motorcycle and went riding with him in Connecticut. This was a huge investment for the WWF. They paid Mike Tyson 3 million dollars to be involved in this angle. The company needed a strong buy rate from the pay per view to break even and/or make a profit. Mike Tyson said years later, that despite earning 3 million from the WWF, he never saw a dime of it. The money went to pay bills and various deep debts that Tyson had accrued. Not only that, but Shane McMahon had told Mike how much Don King was getting paid just being associated with him and that caused Tyson to flip.

Don King apparently made more than what Tyson and King agreed upon. That set off Tyson, who was rumored to physically assault King. A rumor that Tyson vehemently denied. Nevertheless, it caused Mike to split from King after over a decade partnership.

The main event of Wrestlemania 14 saw Steve Austin defeat Shawn Michaels for the WWF title with Tyson making the three count. The ending was booked to have Shawn turn of Tyson leading Tyson to knock HBK out cold. Shawn apparently had issues with that idea, feeling that he was going to be out of wrestling for a while if not permanently due to his back injury and didn’t want fans to see him end his career like that. Michaels allegedly went to McMahon to tweak the ending to make Hunter Hearst Helmsley take the punch and HBK run off to which an agreement was made. The problem was Tyson forgot the altered ending and punched Michaels in the original spot. HBK was livid after the show and wanted to interrupt the post show press conference. He was talked down by Shane and HBK stormed out of the arena.

Wrestlemania 14 ended up getting 2.3 buy rate or roughly 730,000 buys making it at the time the biggest selling pay per view in WWF history. The gamble of hiring Mike Tyson paid off and helped propel the WWF to overtake WCW in their bitter rivalry.