Mike Tyson and Lennox Lewis were two of the best heavyweight fighters of their generation. Some might even go so far as to call them two of the best of all time.

The 1990s were full of great heavyweight battles. Evander Holyfield took part in one of the best trilogies in boxing history with Riddick Bowe and also had two bouts each with Mike Tyson and Lennox Lewis. Holyfield also had an epic bout with George Foreman, who would later go on to recapture the heavyweight crown by knocking out Michael Moorer. Foreman also had an underrated bout with Tommy Morrison. The list goes on and on. One fight that didn’t happen during the decade was Tyson vs. Lewis, who didn’t step in the ring with one another until 2002, which most (myself included) believe was far too late.

So why did it take so long for these two all-time greats to get it on?

Mike Tyson and Lennox Lewis were once sparring partners as teenagers

Lennox Lewis spent a long time as an amateur boxer. He took up the sport as he entered his teenage years in 1978 and won the gold medal at the Junior World Championships in 1983. In preparation for the 1984 Summer Olympics, Lewis was looking for sparring partners and found one in 17-year-old Mike Tyson, who was rising up the amateur ranks himself and also looking to make a run at the Olympics.

The two met on multiple occasions in a Catskills gym in front of Tyson’s legendary trainer, Cus D’Amato, who predicted that the two would someday meet in a big professional fight. Tyson bloodied Lewis’s lip but Lennox, never one to back down, came back and bloodied Iron Mike’s nose. Lewis later recalled those sparring sessions, calling Tyson an “animal” and actually hoped that he wouldn’t fight him again down the line.

Lewis lost in the quarterfinals of the Olympics via decision to Tyrell Biggs, who went on to win the gold medal. Tyson actually never made it LA after losing to Henry Tillman at the Olympic trials. Lewis chose to stay an amateur for four more years so he could win a gold medal, which he did in 1988 in Seoul, beating Riddick Bowe in the finals.

Mike Tyson went the other way and turned pro in 1985 and won his first heavyweight title in 1986 at the age of 20. Lennox Lewis finally joined the professional ranks in 1989 and a showdown between the two seemed inevitable.

Why the two never met in the ’90s

Things got a little crazy in the heavyweight division in February 1990 when Mike Tyson lost the undisputed heavyweight championship to Buster Douglas. Over the next few years, the belts were split up and there were numerous fighters that could officially be considered a champion. Yes, that did lead to some extra fights, which wasn’t a bad thing, but it could get confusing at times on who had what title and who their next challenger would be.

Lennox Lewis actually won the WBC title without beating anybody. He had been named the number one contender after defeating Razor Ruddock in October 1992 and was set up as the challenger to the winner of the Riddick Bowe vs. Evander Holyfield fight a few weeks later. Bowe won but refused to fight Lewis and literally threw the WBC title in the trash. Lewis was named the champion in December. Mike Tyson wasn’t around for any of that as he’d been sentenced to three years in prison earlier that year.

Fast forward to 1995. Mike Tyson was released from prison and returned to the ring that August, promptly knocking out Peter McNeeley in the first round. In a huge upset the year before, Lennox Lewis had been knocked out in the second round by Oliver McCall and lost the WBC title. In May 1995, Lewis knocked out Lionel Butler and then knocked out Justin Fortune less than two months later to become the number one contender for the WBC title. McCall went on to lose the belt to Frank Bruno in September 1995, seemingly setting up a Lewis vs. Bruno bout, a rematch from 1993 in which Lewis knocked Bruno out in the seventh round.

This is where things get tricky. After Lewis defeated Tommy Morrison in October 1995 and Tyson beat Buster Mathis Jr. in December, the WBC opted to give Tyson the shot against Bruno instead of Lewis. In March 1996, Mike Tyson knocked out Frank Bruno in the third round to win the WBC crown. In turn, Lennox Lewis sued to make Tyson fight him and won. But the fight never happened.

Don King offered Lewis four million dollars to step aside so that Tyson could go after the WBA heavyweight champion, Bruce Seldon, with the promise that he’d fight Lewis after. Lewis accepted but never got his shot at Iron Mike. After defeating Seldon in September 1996, Tyson relinquished the WBC title so he could have his long-awaited fight with Evander Holyfield. The WBC crown was declared vacant and Lennox Lewis avenged his loss to Oliver McCall in February 1997, once again becoming champion.

Over the years, many have accused Lennox Lewis of ducking Mike Tyson by accepting the payout from Don King. Others have said that King didn’t want Tyson to have any part of Lewis at that time.

Lennox Lewis destroyed Mike Tyson when the two finally fought in 2002

Mike Tyson lost both of his fights with Evander Holyfield, whom Lennox Lewis would defeat in 1999 for the undisputed title after a draw in their first fight. Lewis suffered yet another upset loss in April 2001 to 15-1 underdog Hasim Rahman but beat him in the rematch in November. Meanwhile, Tyson was beating lesser-name opponents but called out Lennox Lewis for the better part of two years, the most notable offense coming after he knocked out Lou Savarese in 2000. Following the fight, Tyson said he wanted to eat Lewis’s children and that he wanted his heart.

Well, he finally got his chance in June 2002. After years of hoping and waiting, Mike Tyson vs. Lennox Lewis was finally on. And it was not the fight that it should have been. Lewis destroyed Tyson that night in Memphis. Tyson looked good in the first round but Lewis caught him with big shots in the second and then opened up a cut over Tyson’s right eye in the third. Tyson went down for the first time in the fourth and was just spent by the end of the fifth. By the time the eighth round rolled around, Tyson’s face was swollen and Lewis ended it, hitting Iron Mike with a big right cross. Tyson went down for the second time in the round and didn’t make any real attempt to get up.

Many often wonder what would have happened had Mike Tyson and Lennox Lewis fought in their respective primes. But that’s just another “what if” story in sports, isn’t it?