Evander Holyfield and Mike Tyson had a contractual agreement to fight for the undisputed heavyweight championship on November 8th 1991. The highly anticipated event never happened because of an apparent Tyson rib injury and then later was delayed when Tyson went to prison, among other reasons.

Tuesday November 8th marked the 20 year anniversary of the planned Tyson/Holyfield fight date at Caesars Palace, Las Vegas, Nevada.

A caption in the July 22, 1991 edition of Sports Illustrated: Heavyweight champ Evander Holyfield will finally fight Mike Tyson because, after much wheeling and dealing, that’s what both men what.

Mike Tyson, the 25-year-old, No. 1 contender fresh off of four dominating victories since the shocking defeat to Buster Douglas in February 1990, wanted his heavyweight title back. The above SI story said gross for the event projected over $100 million with Holyfield earning a guaranteed $30 million and Tyson $15 million guaranteed.

Tickets for the event ranged from $1200 to $200 dollars at the roughly 15,000 seat arena of Caesars Palace, where many high-profile boxing events were held at the time. Dan Duva, Holyfield’s promoter, and Don King who promoted Tyson, agreed–Tyson vs. Holyfield was to become the richest fight in boxing history.

At the time, before the handshaking and contractual finalities took place, and before the idea of prison for Tyson entered into the equation, two factors blocked Tyson/Holyfield from happening in 1991 – money and George Foreman.

Roughly twelve months before Holyfield and Tyson agreed to terms, George Foreman fought on the undercard of Tyson’s first bout since Douglas defeat against Henry Tillman in June 1990. The Tyson/Foreman twin bill idea meant to build interest for an eventual clash between the two sluggers. After Foreman’s brave losing effort versus Evander Holyfield in April 1991, Don King offered the 42-year-old former champ a $20 million purse to face Iron Mike.

Foreman and his promoter Bob Arum, refused, saying they wanted a rematch with Holyfield.

In July 1991, less than two weeks after Tyson beat Razor Ruddock for the second time, Holyfield/Tyson fight was made to the dismay of Foreman and Bob Arum. Immediately after Holyfield/Tyson signed an agreement for November 1991, Foreman with help from promoter Bob Arum filed a $100 million breach of contract suit against Holyfield.

According to the Baltimore Sun, Bob Arum received a letter from Dan Duva with contract terms for Holyfield vs. Foreman II on July 8th, 1991. Foreman was to earn $12.5 million. Arum learned the following day that Holyfield and Tyson had a contract to fight instead. An enraged Arum said, “They used (Foreman) like a fool.” Holyfield’s team had two offers for Tyson; they could accept the $15 million and fight in November or take $25 million guaranteed to face Holyfield in April, considered step aside money, allowing Holyfield to give Foreman a rematch.

Tyson took the $15 mil. Tyson told Don King, “Forget the money.” He wanted the heavyweight belt again by any means. The undefeated, undisputed champ, 29-year-old Evander Holyfield stood in his way.

Holyfield preferred Tyson over Foreman. Despite beating Douglas who beat Tyson, The Real Deal was not fully recognized as the heavyweight champion in the public eye at the time. Tyson’s loss to Douglas was viewed by many as a fluke. It seemed a matter of time before Iron Mike would be crowned king again. Leading up to the fight Holyfield said, “You can’t hide from the fact that Tyson’s the man. I wanted to fight Tyson because he was champion. Even if he was not champ now, I still want to fight him.”

The New York Times wrote that Tyson vs. Holyfield sold out in 14 days, breaking a Caesars Place record previously held by the 1987 Hagler-Leonard fight which sold out in 16 days. Although excitement was brewing for the heavyweight showdown, Tyson’s legal troubles began to surface.
On August 3, 1991, the New York Times also reported a grand jury investigation involving Mike Tyson about a complaint filed with the Indianapolis Police Department by an 18-year-old woman accusing the ex-champ of sexually assaulting her on July 19th, 1991.

The NY Times article says a representative from the Indianapolis Police Department expected a special grand jury to investigate the Tyson issue within the week.

Despite the potential roadblock of what was the richest fight in boxing history, Seth Abraham, of TVKO-PPV told the NY Times, “We are going forward, (and) awaiting developments.”

On October 20th 1991, The Chicago Tribune stated Tyson pulled out of his bout with Holyfield because of a rib injury. “The announcement came only hours after a request by Tyson to delay his rape trial was denied by Marion County (Ind.) Judge Patricia Gifford,” said the Tribune.

Meanwhile a frustrated Dan Duva told the Tribune that Tyson injured his ribs on October 8th, nearly two weeks before Tyson cancelled. Don King hoped to reschedule the event for January 20th 1992, one week before Tyson would go to trial for rape and eventually get convicted. Nothing came of it.

In the end, Foreman never got his rematch with Holyfield and Tyson had to wait four years to get another fight. But what would have happened if a close to his prime Mike Tyson took on an agile, quick, undefeated heavyweight champion Evander Holyfield? Some find pre-prison era Tyson too ferocious, others say the outcome would have been the same in ’91 as it was in 1996 and 1997 when Holyfield officially beat Mike Tyson twice. Tyson vs. Holyfield November 8th, 1991 is an argument that can never be answered but an argument nonetheless.

Evander Holyfield 26-0 vs. Mike Tyson 41-1
Opinion Poll – Below is a compilation of viewpoints on the fantasy bout from boxing writers, trainers, and fighters. Who would win a fight between Mike Tyson and Evander Holyfield in November 1991?

Jack Hirsch – President of the Boxing Writers Association of America
What amazes me is that people always bring up Muhammad Ali’s three year layoff as a reason he was beaten by Joe Frazier, yet completely ignore that Tyson was out of the ring for a similar amount of time.  When Ali lost to Frazier he was 29, Tyson was 30 when beaten by Holyfield.

Had they met in 1991 when their first fight was scheduled to take place, it would have been a better Tyson for sure, but I still don’t think it would have been enough. When you get past the charisma and mystique of Tyson, Holyfield was a better fighter and much stronger mentally.  He always had this thing about wanting to prove he was superior to his great rival Tyson.  Mike did not quite have the same passion about proving he was better than Holyfield, in part because he was made out to be invincible and probably bought into it to an extent.

Holyfield on points in a good competitive fight would have been the likely result, had the two squared off in 1991 as originally planned.

Robert Guerrero – Multiple division champ and pound for pound contender
Mike Tyson had already lost to Buster Douglas so his aura of invincibility was tarnished coming into to his fight with Holyfield. As it turned out, Holyfield wasn’t intimidated when they finally fought and he defeated him.  Tyson was never the same after his loss to Douglas so no matter what, I think Holyfield would have beaten him regardless of the circumstances.

Danny Jacobs – Middleweight prospect
Personally I think Iron Mike would have beaten Evander for the simple fact that Mike already took an L. Tyson knew another loss wouldn’t be good.  He would have trained the hardest he had ever trained and would have been 100% focused. I pick Tyson, and not because I am from Brooklyn.

Thomas Hauser – Chairman of BWAA Membership Committee/Award winning author
Tyson was a better fighter before he went to prison than afterward.  But by 1991, he’d already lost to Buster Douglas and was on a downward slide.  Given what happened in the two Tyson-Holyfield fights, it’s hard to pick against Evander.  But I still think that Tyson at his best (circa 1988) was better than Evander at his best.

David Avila – West Coast Bureau Chief of TSS/Founder of Uppercut Magazine
I was very disappointed because I had a debate with a good friend of mine over this fight. For two years I had insisted that Evander Holyfield would be the guy to beat Mike Tyson if they met. We had a bet going on and it had to wait a few more years. I had always felt that Holyfield’s style and toughness was a perfect match for Tyson’s aggression. It was a perfect style match up.?

Terry Norris – Former four-time junior middleweight champion
Tyson would have knocked him out, he was too strong. And Holyfield was a very good fighter but Tyson was the man back in ‘91. Much respect to both those guys. They are two great fighters.?

Brad Cooney – CEO www.8CountNews.com
I think the same thing would have happened to Tyson in 1991 as what happened to him in 1996/97. Tyson met his match against a guy in Holyfield that had boxing skills.

Ryan Maquinana – www.Boxingscene.com
By 1991, despite two good wins over Razor Ruddock, Tyson wasn’t the same complete fighter he was when he was undisputed champ, especially after he took that first loss against Buster Douglas just a year before then. Holyfield was on a roll, stopping Douglas and decisioning Foreman before stopping a determined Bert Cooper who gave him fits early. I think I’d have to favor Holyfield if they met in ’91. But the Tyson who stopped Trevor Berbick was just an awesome machine. I think he’d beat the ’91 Holyfield.”

Lyle Fitzsimmons – www.CBSSports.com
That’s a toughie. I’m not as reverential of Mike as a lot of people. I think he lost to Buster because of the style, not because of corners or marriages or anything else. So I think a heavyweight Evander would have always been a task for him, because Evander was a better all-around fighter. That said, I think it would have been far less decisive in 1991 than it was five years later.

Ryan Songalia – www.RingTV.com
We want to believe that Mike Tyson, prior to prison, would have beaten Evander Holyfield. But the truth had been on the wall for some time. Tyson had become increasingly reckless under his Don King-appointed trainers, and basically became an explosive street fighter. Tyson had shown his defensive holes in the first fight with Frank Bruno, as well as the two fights with Ruddock. I feel that Holyfield just knew enough tricks to keep Tyson off balance and exploit the holes.

Maybe Tyson doesn’t get stopped like in the first fight years later, but I think Holyfield would have gotten him.

Tim Starks – Founder of www.Queensberry-rules.com
You can’t talk about a Mike Tyson vs. Evander Holyfield “what if” in 1991 without rewinding to Tyson-Buster Douglas in 1990. The usual explanation for how Douglas beat Tyson was that the bully had been unmasked, that the balloon of intimidation and invulnerability finally got punctured by an inspired Douglas who had nothing to lose. I think that’s part of the way true. But spending more than one weekend watching the Tyson marathons on ESPN Classic, I always notice how much his technique degenerated from the days of Cus D’Amato to the fateful night in Japan. He had stopped bobbing and weaving so much, lost track of his body attack, and the combination punching that helped make his blend of speed and power so fearsome had all but disappeared.??On the rehab trail, Tyson rediscovered some of his form, and some of his nerve, against Razor Ruddock, where his body punching was painful to behold and he responded with grit to being rocked by Razor. That offers at least the chance that Tyson might have fared better against Holyfield than he eventually did. But we’re also talking about prime, unbeaten heavyweight Holyfield in ’91 — there were not yet any of those draining wars with Riddick Bowe that would later come, no struggles with hepatitis A. I’ll take prime heavyweight Holyfield over diminished Tyson every day. It’s just too bad we have to daydream about it, instead of getting to witness it.

Martin Mulcahey – www.Maxboxing.com

Styles makes fights, but I think timing can play an equally important factor which is why I lean slightly towards Tyson in this time-frame. From late 1990 to late 1991 Tyson fought in three month intervals, which was key to keeping Tyson focused and sharp since his style was dependent on timing. Two good wins over Razor Ruddock and evisceration of Alex Steward showed he was sharp, while at the same time Holyfield was turning in sub-par performances against Bert Cooper and Larry Holmes. This version of Tyson defeats Holyfield, but only after surviving a furious Vander comeback in the championship rounds.

Mario Ortega – www.15Rounds.com
While we will never quite know what would have happened if 1991 versions Evander Holyfield and Mike Tyson would have clashed in the ring, it is my belief that “The Real Deal” would have still prevailed, much as he did 1996. With everything that was going on in his life at the time, I don’t think Tyson would have been up mentally for the challenge of a prime Holyfield. I believe Holyfield would have survived the early onslaught and out boxed Tyson down the stretch, perhaps taking a unanimous decision.

Virgil Hunter – Trainer of super middleweight champion Andre Ward
Holyfield always had the style to beat Mike Tyson. He had more boxing skill. Tyson at the time was great but Holyfield would beat him. You could just watch Holyfield’s fight with Dwight Muhammad Qawi to figure that out. Qawi obviously was not as strong as Tyson, but he threw similar combinations. Holyfield was prepared to defeat Tyson in 1991 because he fought Qawi.

Ramon Aranda – Managing Editor of www.3morerounds.com
In my opinion Tyson could have beaten Holyfield in 1991.  Now granted, Tyson had been exposed by Buster Douglas and was not the same fighter he was during his prime years as heavyweight champ.  However, he had a lot to prove and Holyfield, at that particular point in time, was quite receptive to going toe-to-toe with opponents, as we saw in his fights with Riddick Bowe, and Bert Cooper.  That type of strategy would have been his downfall.

The Holyfield we saw against Tyson in 1996 was more conservative with his punches and a better defensive fighter, which was to his benefit against an aggressive Tyson.  In 1991 however, Holyfield would have slugged it out and gotten knocked out.