Updated: Aug 6, 2019
The Road Back
James 'Buster' Douglas was scheduled to face top contender Evander Holyfield in June 1990, but as he was in a legal dispute with Don King, that bout was pushed back to the September. Mike Tyson, however, did return to the ring on the 16th June 1990 against Henry Tillman.
Tillman did manage to beat Tyson twice in the unpaid ranks, for the 1984 Olympic Trials, finally winning gold in the heavyweight division in Los Angeles. But his professional career didn't emulate his amateur resume.
He started out at cruiserweight and won ten in a row, including a heavyweight contest against Tyson foe Reggie Gross, winning a ten round unanimous decision. Tillman then fought Bert Cooper for the NABF cruiserweight title. Cooper knocked him down twice in the second round, firstly by a left hook, then again by an overhand right to the head before going on to winning a twelve unanimous decision.
He went on to win four bouts before taking on WBA cruiserweight champion Evander Holyfield on the 14th February 1987. This was the first time that two American medalists from the LA Olympics (Holyfield was a bronze medal winner in the light-heavyweight division) faced each other in the pro ranks. Holyfield virtually won every round as he knocked Tillman down in the second before retaining his title via the three knockdown rule in the seventh.
Tillman then moved up to the heavyweight division, winning three, then suffering back-to-back losses against Dwain Bonds and Willie de Wit. He won his next three before being Tyson's first opponent since losing his undisputed heavyweight championship.
Tyson had a new chief trainer on board. Richie Giachetti, who helped guide Larry Holmes to the world heavyweight championship, was the man to instil the skills that were missing since Kevin Rooney was sacked. Aaron Snowell and Jay Bright were still there to assist.
The fight took place at Caesars Palace, Las Vegas. George Foreman beat Adilson Rodrigues in the second round on the undercard, but the jovial air that surrounded 'Big' George, turned to violent menace as Tyson made his way to the ring.
As the bell rang Tyson had to chase the retreating opponent around the ring. Tillman worked behind a jab, but his sole purpose was to stay out of trouble. He did manage to land a right, but it was the man from Catskill, New York who was landing the telling punches. Tillman backed to a ring post and threw a right hand, but Tyson beat him to it and landed a overhand right that caught his man on the temple. Tillman was down and out as referee Richard Steele counted out the glazed-eyed man at two minutes 47 seconds of the first.
Tyson rushed over to help his stricken friend. "We often hang out together in Los Angeles, I've got a home there, me and Henry are good friends, what happened in the ring was just business," explained Tyson.
Douglas Defends the Title
James 'Buster' Douglas, after many months of lawsuits with promotor Don King, finally defended his crown on the 25th October 1990, against the undisputed number one contender Evander Holyfield. Had it not been for Douglas' upset victory, then the former undisputed cruiserweight world champion would've faced off against Tyson in June 1990.
The new champion had put on a lot of weight since beating Tyson and started his training camp really heavy. At the official weigh-in Douglas scaled 246 lbs, 14.5 lbs more than he was in Tokyo. Holyfield, who was always in magnificent condition came in at 208 lbs.
Holyfield controlled the first two rounds, using his speed and taking advantage of the champion's lack of conditioning. Then in the third, Douglas committed the cardinal sin of boxing and fired a lead right uppercut. Holyfield stepped back and countered with a right to the jaw. Douglas fell to the canvas. He lay on his side, wiped his face with his gloves to check for blood, before rolling onto his back with no intention of beating Mills Lane's count of ten. Holyfield became the first cruiserweight to step up and become heavyweight champion of the world.
Douglas made $24,075,000, the largest purse ever at the time compared to Holyfield's $8,025,000, but the championship was far more important to Holyfield than the financial gain, and it looked like the belts were in a safe pair of hands before Tyson got his chance.
Tyson Marches On
Alex Stewart was next for Tyson, scheduled for the September, but that contest was postponed until the 08th December 1990, due to Tyson suffering a cut during sparring.
British born Stewart, who represented Jamaica in he 1984 Olympics, set up home in Brooklyn, New York and in September 1986 turned professional. He won twenty four in a row, all stoppage victories, before having a crack at Evander Holyfield's WBC Continental Americas heavyweight title. In what was Holyfield's fifth heavyweight contest and his second defence of his title, since stepping up a division.
Holyfield had been in with the higher calibre of opponents and the fist two rounds showed his class as he got inside Stewart, throwing short hooks and uppercuts and neutralising his opponent's main asset, the straight right. He even cut Stewart in the second and at the bell the challenger's face was reddened.
In the fifth round Stewart landed with a left-right-left combination that rocked Holyfield. Stewart was landing with his right and getting in some left hooks too, but 'The Real Deal' weathered the storm and stopped his brave opponent in the eighth, with the ringside physician stopping the fight due to the badly cut right eye.
Alex Stewart stopped his next two opponents, before going in with another world class heavyweight - 'Iron' Mike. Tyson put Stewart down with the second right hand he landed. Tyson swarmed all over his opponent. In his wildness to land the killer blow Tyson missed with a right and found himself on the floor, which was ruled as a slip.
They went at each other mid ring and Stewart got his jab going, but as he was forced to the ropes a flush Tyson right put him down for a second time. He was up at the count of nine, with Frank Cappucino asking "Are you all right man? Do you want to continue?"
The answer was yes, but with one-minute 40 seconds left of the round and the three knockdown rule in effect, Tyson had plenty of time to finish things. Tyson was more calculated in his work and landed a good left hook to wobble Stewart to the ropes. They came to the centre of the ring and Tyson threw a left-right, which staggered Stewart to the ropes. A left hook from Tyson floored his man for the third and final time, with the official time being two minutes and 27 seconds.
This proved to be Tyson's last fight with Home Box Office. Don King and Tyson signed a contract with the rival TV network Showtime, as they wanted HBO to get rid of their man Larry Merchant. They refused, hence the change of TV companies.
18th March 1991 was Tyson's next ring appearance. This time he faced Donovan 'Razor' Ruddock in a bout that pitched the undisputed number one contender (Tyson) against the undisputed number two ranked heavyweight, in what was a final eliminator for Evander Holyfield's crown.
Donovan Ruddock was the most feared heavyweight on the planet, behind Tyson. These two were meant to face each other in November 1989 in Edmonton, Alberta, Canada. Tyson pulled out of that date due to illness. The bout was postponed, then cancelled.
Canadian Ruddock started his career as a cruiserweight in March 1982. He won five fights and drew his sixth contest with Phil Brown. He then moved up to heavyweight and outpointed Conroy Nelson. In April 1985 he lost to journeyman David Jaco, where he said an asthma attack caused his retirement. He won his next three, then outpointed former WBA champion Mike Weaver over ten rounds.
On the 28th May 1988, Ruddock needed just one round to capture the vacant Canadian heavyweight title against Ken Lakusta. In his twenty-fourth contest he was put down in the second round by another former WBA champion, James 'Bonecrusher' Smith. He got up to knock out Smith in the seventh. On the 04th April 1990 he stopped yet another ex WBA champion, Michael Dokes in the fourth, using his 'left smash' (hook come uppercut.) Kimmuel Odum was stopped in the third and on the undercard to Tyson-Stewart he stopped Mike Rouse in one.
The contest took place at Las Vegas' Mirage Hotel. Ruddock was probably the only fighter that Tyson faced who didn't fear him. 'Mighty' Mike Tyson, as ring announcer Jimmy Lennon Junior called him started with a couple of jabs, then a right, but Ruddock let go a wild left hook that was only whiskers away from Tyson's chin. Both men landed some good punches in an even first round.
It was Tyson who landed a left hook in the second round, which floored Ruddock. It was more of a case of being off balance, rather than a devastating shot from Tyson. Richard Steele administered a count and the two of them got back to landing blows, with some fouling by Tyson.
They were both having successes in the third round, but with seconds remaining Tyson's left hook put the Canadian to the canvas again. Ruddock smiled as he got up and he went back to the corner to get the 60 second breather. Tyson came out punching in the fourth, but Ruddock had recovered and both men landed with bombs. Ruddock stunned Tyson with a left hook - which perforated Tyson's eardrum, in the sixth round.
The seventh ended controversially. Tyson landed with a right to the body and followed it up with a left to the head. Ruddock wobbled towards the ropes, with Tyson unloading. Richard Steele stopped the advancing Tyson and waved the finish. As Ruddock crashed into the ropes he suddenly realised that the fight was stopped. "What?' He asked.
Steele would later defend his premature stoppage by saying. "We're in the boxing business, not the killing business." A rematch was scheduled for the 28th June 1991.
Holyfield Defends the Title
'Big' George Foreman got his shot at Holyfield on the 19th April 1991. He was looking to regain the championship he lost to Muhammad Ali in Zaire on the 30th October 1974. Foreman won five in a row, all stoppages before he lost to Jimmy Young on a twelve round unanimous decision on St Patrick's Day 1977. Foreman retired and just over ten years later returned to the ring with a fourth round TKO victory over Steve Zouski. He went 24-0 (23 KO's) in his second career before facing Holyfield.
After Evander Holyfield knocked out 'Buster' Douglas for the title, the WBC, WBA and IBF stated that the winner of that bout must face their number one contender Mike Tyson next. The WBA and IBF backed off the mandate, but the WBC did not and threatened to strip the champion. Holyfield successfully sued the governing body with the judge ruling the WBC couldn't strip him of the belt.
The 'Battle of the Ages' took place at the Trump Plaza Convention Centre in Atlantic City. The twenty-eight year old champion won an unanimous decision 116-111, 117-110 and 115-113. Though Holyfield hurt the forty-two year old challenger in rounds three, seven and nine, he didn't have it all his own way as Foreman stunned him in rounds two, five and seven. The victory would pave the way for the winner of Tyson-Ruddock II.
Tyson and Ruddock picked up from where they left off in March, as both men traded big punches. A right wobbled the Canadian towards the end of the first and both men threw shots after the bell. Referee Mills Lane had his work cut out.
The referee stopped the action in the second and told Tyson to keep his punches up. As soon as they resumed, an overhand right put Ruddock to the canvas. Tyson teed off on his opponent, but he couldn't finish him, as the bell sounded to end the round.
The third and Tyson, who was still landing bombs, wasn't bobbing and weaving like he used to do and was getting caught by lefts and rights. In the fourth round Ruddock landed his left smash and followed up with a right uppercut. As he was standing square on as he threw the punch, Tyson floored him with a straight right hand. Ruddock got up right away.
Both fighters had the power to hurt the other, Ruddock was docked a point in the eight for hitting after the bell, whilst Tyson was deducted points in rounds four, nine and ten for low blows. Each man had their gum shields knocked out of their mouths. The Canadian did stun Tyson in the tenth, but the former champion got through the crisis and eventually heard the final bell. Ruddock's left eye was swollen and he suffered a broken jaw. The judges scored it 113-109 and two scores of 114-108 all in favour of Mike Tyson.
Tyson and Holyfield were scheduled to meet on the 08th November 1991 at Caesars Palace, Las Vegas. Finally the world was going to see the richest fight in history. The champion was guaranteed $30,000,000, the challenger $15,000,000.
Tyson was then indicted on charges of raping beauty pageant Desiree Washington in Indianapolis, Indiana on the 09th September. With his court case set for the following January, the fight still looked like to be going ahead.
But on the 19th October it was announced that Tyson had damaged his ribs during training and the bout was postponed. No new date was announced and Holyfield selected the Italian Francesco Damiani to step in for Tyson in Atalanta on the 23rd November. Damiani then pulled out with an ankle injury and Bert Cooper stepped in as the substitute for a substitute.
The WBC didn't sanction the fight as Cooper wasn't ranked by them. He wasn't ranked by the World Boxing Association either, but they sanctioned the contest along with the IBF, who had Cooper at No 12.
Things looked good for the champion as he floored 'Smoking' Bert Cooper with a left to the body. Then in the third the unthinkable happened; Cooper hurt the champion with a right and a follow up barrage had Holyfield needing the ropes to keep him upright. He took the first count of his career.
Cooper was finding the champion easy to hit and an upset looked likely, until Holyfield rallied in the seventh round and after twenty-four unanswered punches, Mills Lane stopped the fight with two seconds remaining of the round.
Tyson's trial started on the 27th January 1992 and he was convicted of rape on the 10th February 1992. He wouldn't fight again until the 19th August 1995.
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