Boxing legend Mike Tyson made history as a heavyweight champion – but he failed to fulfil his dream of representing the USA at the Olympic Games.

‘Iron Mike’, 58, was a true boxing prodigy in his early days, becoming the youngest-ever heavyweight champion as a 20-year-old. His undisputed reign lasted for more than two years, building up a fierce 37-0 record with only four decision victories, all by the age of 23.

There were signs of Tyson’s future dominance during his amateur career, twice winning the Junior Olympic Games and becoming a National Golden Gloves champion in 1984. However, this was not enough to earn him a spot at the Los Angeles Olympics later that year.

Tyson, who is scheduled to fight Jake Paul this November, competed at the Olympic trials but lost a points decision to Henry Tillman in the final. Despite the defeat, Tyson was handed a rematch a month later but failed to make it count, suffering a split-decision loss that ended his Olympic hopes.

“When they announced the decision, I couldn’t believe they gave it to Tillman,” Tyson recalled. “The whole amateur boxing establishment hated me.

“They didn’t like my cocky Brownsville attitude. I was behaving myself but you could still see that New York swagger coming out.”

Tillman may not have reached the same heights as Tyson in the professional ranks, but he did go on to win Olympic gold in his hometown, defeating Canada’s Willie DeWit in the final. However, when the two men crossed paths for a third time in their careers, the outcome was much different.

Mike Tyson (R) and Henry Tillman (L) fought for a third time in 1990 (Image:

Focus on Sport/Getty Images)

After losing his undefeated record to Buster Douglas in a fight that shocked the world, Tyson’s comeback was scheduled against Tillman in June 1990 – six years after Tyson’s Olympic heartbreak. Entering the ring with a point to prove, Tyson avenged his two defeats by stopping Tillman with a brutal first-round KO.

Tillman retired with a 25-6 record, losing his sole cruiserweight world title fight to Evander Holyfield in 1987. However, he still had his Olympic triumph in Los Angeles to savour.

“Winning the Olympic gold medal at home was so special,” Tillman told USA Boxing in 2020. “My mother and father were there with a lot of my South Central friends.

“That really made it over the top special. I was the most unlikely to make it, but my mother and father kept me grounded.”