Henry Tillman is a name that does not ring a bell for casual boxing fans, while Mike Tyson is one of the most well-known figures in the sport.

It is consequently hard to believe that Tillman once crushed Tyson’s Olympic dreams while they were both amateur boxers, preventing his opponent from competing at the 1984 Games in Los Angeles.

Tillman twice outpointed Tyson to earn his spot at the Olympics
Tillman even went on to win a gold medal, but he was unable to replicate the success he found as an amateur once he turned professional.

His story is one of unfulfilled potential and is in stark contrast to Tyson’s rise to prominence.

Denying Mike Tyson his Olympic dream

Tillman was born in Los Angeles in 1960, growing up in tough neighbourhood South Central and using boxing as an escape.

He quickly became the standout American heavyweight in amateur boxing in the early 1980s. Aged 23, he was given the chance to represent his country at a home Olympic Games.

Standing in his way was a young amateur boxer from Brooklyn called Mike Tyson, who had already won gold at the Junior Olympics in 1981 and 1982.

The pair came up against each other at the US Olympic trials in 1984, with Tillman winning.

Tyson had another chance to qualify for Los Angeles 1984, this time in a box-off at the glamorous Caesars Palace in Las Vegas. Tillman was the opponent yet again, and Tyson lost for a second time.

Tyson was devastated
His Olympic dreams were crushed and the young boxer could barely contain his frustration. He quickly left the ring and walked out of the venue, pummelling a tree outside.

“When they announced the decision, I couldn’t believe they gave it to Tillman,” Tyson later said. “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.”

In the end, Tillman went on to win gold at the Los Angeles Olympic Games. He defeated Canada’s Willie DeWit by unanimous decision in the heavyweight final, securing one of the most prestigious titles in amateur boxing.

Tillman proudly stood atop the podium in 1984
“Winning the Olympic gold medal at home was so special,” Tillman later told USA Boxing. “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.”

Transition to professional boxing

Riding high on his Olympic success, Tillman turned professional in 1984 with great expectations.

Although the transition from amateur to professional boxing is notoriously challenging, Tillman showed early promise as he racked up a series of victories.

But, despite his encouraging start, Tillman’s professional career soon began to falter. His first significant setback came in 1987 when he faced Bert Cooper, a hard-hitting heavyweight contender.

Tillman was knocked out in the eighth round, a loss that marked the beginning of a downward spiral in his career.

His struggles continued as he faced more defeats against prominent fighters. One of the most notable losses came against Evander Holyfield in 1988. Holyfield, who would later become a heavyweight champion, defeated Tillman in a seventh-round knockout.

Tillman and Tyson met for a third time in 1990

In 1990 came an encounter that Tyson had likely been looking forward to for several years. He came up against Tillman for a third time, this time in the professional ring.

Tyson may have avenged his amateur defeats, however, it was never personal between him and Tillman. Tyson travelled with the Olympic team in 1984 to earn experience and it was Tyrell Biggs he really hated.

Not that this meant ‘Iron Mike’ would show Tillman any mercy in the ring.

Tyson had become a global superstar and heavyweight champion by then, but had recently lost his title to Buster Douglas in a massive upset.

The professional fight was very different from their amateur encounters

Tyson looked to help Tillman up after his KO
He was on a comeback trail and the fight was heavily publicised due to the pair’s amateur history, but it ended swiftly with Tyson’s connecting with Tillman’s temple and winning via a first round knockout.

This bout effectively highlighted the stark contrast between their professional careers and cemented Tyson’s dominance over his former amateur rival.

Retirement from boxing

Following the loss to Tyson, Tillman’s career never recovered. He continued to fight sporadically but without much success.

His final professional record stood at 25 wins, six losses, and one draw, a far cry from the expectations set by his amateur achievements.

Tillman retired from professional boxing in the mid-1990s, leaving behind a career that had promised much but delivered little in terms of lasting success. He became involved in coaching and mentoring young boxers, using his experiences to guide and inspire the next generation.

His career was in great contrast to Tyson, who was the undisputed world heavyweight champion from 1987 to 1990 and in his prime was widely considered one of the greatest boxers in the world.

Despite this, Tillman can still boast that he beat Tyson twice, and even went on to win an Olympic gold medal.