In October 1989, the contracts for a fight between Mike Tyson and Evander Holyfield were signed and sealed for a fight in the summer of 1990. The pair finally met in November 1996.
The story of how great heavyweight fights get made, collapse, surface again, vanish, and finally take place is one of boxing’s most ridiculous rituals.
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The Tyson and Holyfield saga was interrupted by prison, chaos outside the ring, shocking defeats in it, and the growing greed of all involved; the ongoing struggle to get Tyson Fury and Anthony Joshua in the ring is not quite as dramatic, once you put it in perspective.
Evander Holyfield (right) stopped Mike Tyson in their first fight (Getty)
Joshua first called for the fight in April 2016, after winning the world heavyweight title; Tyson and Holyfield had been on an inevitable collision course since a night in early 1984 at the American Olympic boxing trials, when they had clashed over a pool-table incident.
Heavyweights hold grudges for a long time.
The wait for Tyson and Holyfield was worth it; their fights were magnificent and controversial affairs, the last fights in the final days of the heavyweight business being sport’s greatest crown. The Fury and Joshua fight, which looks likely for Cardiff on 11 December, will not disappoint.
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The first Holyfield and Tyson fight, the one scheduled for Atlantic City on 18 June 1990, was abandoned when Tyson was knocked out by Buster Douglas and lost his world title – and invincibility – in February of that year. Instead, Holyfield knocked out Douglas and that made a Tyson fight even bigger.
It was agreed again after some seriously bad-tempered sessions between Dan Duva, Holyfield’s promoter, and Don King, Tyson’s promoter; Duva had the advantage because he now had the champion.
The deal was finally done on 11 July 1991, at a hotel in New York, and the fight was set for 8 November 1991 at Caesars Palace in Las Vegas. It was boxing’s biggest fight, the boxers would split a guarantee of $45m (Holyfield receiving $30m), and it was expected to gross $100m.
On 17 July 1991, Tyson travelled to Indiana to attend a beauty pageant; he was arrested and charged with rape a couple of days later. The fight was pushed back, but not scrapped, and there was a working date in January 1992, a month before Tyson’s trial.

Tyson Fury (centre-right) and Anthony Joshua exchanging words after Fury’s win over Arslanbek Makhmudov in April (Getty)
Tyson injured a rib, and the fight was off. Tyson was found guilty, went to prison, and it looked like the fight was off forever.
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However, there is no such thing as a lost cause in boxing, and as soon as Tyson was released in the late summer of 1995, the men in charge were talking about the fight. It was never dead, just resting ominously, and the money was still there.
In early 1996, Tyson regained the world heavyweight championship. During Tyson’s incarceration, Holyfield had lost, won and then lost the heavyweight title again.
Their fight was officially announced for November of 1996 at the MGM and Holyfield was given no chance; he won on the night and then he won the Bite of the Century rematch the following year.
The Fury and Joshua fight has been easy to make compared to the ancient boxing negotiating skills, patience and determination needed to get Holyfield and Tyson in the ring.
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