Henry Tillman: The Boxer Who Managed To Beat Mike Tyson Twice

In the 1980s, legendary boxer Mike Tyson made waves in and out of the ring. Before he became the youngest boxer ever to win a heavyweight title at 20, he was a self-described "monster" (via ESPN). Heavy reports that Tyson was arrested 40 times before he turned 12 for burglaries, pick-pocketing, and snatching jewelry. ESPN further states that Tyson was bullied as a child, before he grew up to become one of the greatest and most feared heavyweight boxers of all time.

Nicknamed "Iron Mike," Tyson became the undisputed heavyweight champion in 1987. He continued his reign until 1990, when 23-year-old underdog Buster Douglas ended his winning streak, causing a stir in the boxing world (via Bleacher Report).

Synonymous with the sport of boxing (apart from Muhammad Ali), Tyson could never win an Olympic medal for the United States despite winning the 1981 and 1982 Junior Olympics as an amateur. Per Sportskeeda, his dreams of representing his country at the largest sporting event in the world were shattered by boxer Henry Tillman (above), who went on to win the gold at the 1984 Los Angeles Olympics.

Tyson's most worthy opponent

Tillman, age 22, and Tyson, age 18, were first-timers at the 1984 U.S. Olympic trials in Texas. Both athletes had troubled childhoods and learned to box as a way to fight back, per Sportscasting. With Evander Holyfield, the Southeastern Regional Champion, and Pernell Whittaker, the lightweight silver medalist at the 1982 World Championships, in the running as well, the competition was undoubtedly rife.

The judges chose Tillman as Tyson's most worthy opponent after he defeated his rival 5-0 in a close heavyweight final. Tillman won the first bout, 4-1 at the Olympic box-offs and left Tyson sobbing, bitter and angry (via Greensboro). "Mike was a beast, period," Tillman told Boxing Scene. "He could fight at an early age. Some guys are great amateurs but didn't do well as pros. It all depends on their styles, and Mike's was more suited for the pros."

In his comeback fight after his shock defeat to Buster Douglas in 1990, Tyson faced Tillman in the boxing ring for the first time since the 1984 Olympic trials. With a single smashing right hand, he knocked out Tillman in the first round to exact his revenge (via The New York Times).

The making of a fighter

Per the Los Angeles Times, Tillman was a novice who quickly rose to become Olympic heavyweight champion under the guidance of former featherweight boxer Mercer Smith, whom he met at a California Youth Authority facility in 1981. "Henry could have been another Ali," said Smith. "He was a beautiful boxer, so smooth. ..."

Tillman emerged from the 1984 Olympics as an inspirational hero in his old neighborhood in South-Central Los Angeles. According to the Los Angeles Times, he often flashed his Mercedes convertible, wore designer clothes, and flaunted his gambling skills. In 1987, he married Gina Hemphill, the granddaughter of decorated track and field legend Jesse Owens.

Tillman retired in 1996 with a record of 25-6 with 16 knockouts. "Henry was not only a top-notch fighter, but he's an extremely well-rounded individual who has so much to offer even during a short conversation," Chris Cugliari, director of USA Boxing Alumni Association, told Boxing Scene. "He's the quintessential USA Boxing Alumnus for our current generation of champions to learn from, and we're proud of everything he has done for USA Boxing."

His own fall from grace

Besides his vicious punches, Tyson is infamous for his behavior inside the ring and out. He spent three years in prison for rape in 1992. According to NPR, Tyson was fined $3 million for biting off a piece of Holyfield's ear during their heavyweight title encounter in 1997. However, it didn't end the boxing legend's erratic behavior. In 2007, Tyson had to spend 24 hours in prison, serve three years of probation, and undergo 360 hours of community service for felony drug possession (via Sportscasting). "The man I've become? Baddest Man on the Planet? I wasn't half the man I ever thought I was," he told The Guardian. "I'm a pig. I have this uncanny ability to look at myself in the mirror and say: 'This is a pig. You are a f**king piece of s**t'."

After becoming a top-notch fighter, though, Tillman too hit rock bottom. According to the Los Angeles Times, he was imprisoned for drug use, grand theft, battery, and armed robbery during his teenage years. In 1994, he was sentenced to 32 months in prison after pleading guilty to credit card fraud. Seven years later, Tillman was found guilty of murder and voluntary manslaughter. Per the Los Angeles Times, Tillman fired a .38-caliber revolver outside the Townhouse nightclub in 1996, killing one and severely injuring another. He was released in 2002, but in July 2004, Tillman was sentenced to 37 months in prison after he pleaded guilty to federal identity theft charges (via ESPN). Per Boxing News, he became a trainer to IBF world heavyweight champion Charles Martin in 2016, and runs Henry Tillman Championship Boxing Club in the Los Angeles area.