On June 28, 1997, Mike Tyson bites Evander Holyfield’s ear in the third round of their heavyweight rematch. The attack led to his disqualification from the match and suspension from boxing, and was the strangest chapter yet in the champion’s roller-coaster career.

Mike Tyson enjoyed a rapid rise to stardom. In 1986 he became the youngest heavyweight champion in history by beating Trevor Berbick at just 19 years old. By 1989, however, Tyson had begun a long downward spiral into sports infamy. His erratic behavior included marrying and divorcing actress Robin Givens (after being accused by her of domestic violence), firing and suing his manager, breaking his hand in an early morning street brawl and two car accidents, one of which was reportedly a suicide attempt. Tyson also fired trainer Kevin Rooney and replaced him with notorious promoter Don King.

Unable to keep his focus on boxing, Tyson, once thought unbeatable, lost the heavyweight title after being knocked out by 42-to-1 underdog James “Buster” Douglas in a stunning upset on February 11, 1990. In 1991, Tyson was accused of rape by Desiree Washington, a contestant in a beauty pageant he was judging in Indianapolis, Indiana. He was convicted on February 10, 1992, and served three years and one month in a federal penitentiary.

Once released, Tyson regained his heavyweight belts and then planned a bout with Evander Holyfield, a clean-living, religious former heavyweight champion from Georgia who was considered the best heavyweight challenger for Tyson after number-one contender Lennox Lewis, who Tyson refused to schedule. Holyfield had retired in 1994, but the prospect of a huge payday proved tempting, and on November 9, 1996, the underdog Holyfield shocked the boxing world by beating Tyson in an 11th round TKO to win Tyson’s WBA title.

Holyfield came into the widely anticipated rematch on this day in 1997 even stronger than he had been for the first fight. In the first round, he hit Tyson hard with body shots while Tyson flailed away, ignoring the science of boxing his trainer had promised he would employ. By the end of the round, the crowd chanted Holyfield’s name, turning on the usual fan favorite Tyson. In the second round, Holyfield head-butted Tyson, opening a cut over Tyson’s right eye.

In the third round, Tyson lost what composure he had left. He spit out his mouthpiece, bit off a chunk out of Holyfield’s right ear and then spit it onto the canvas. Though Holyfield was in obvious pain the fight resumed after a brief stoppage, and then Tyson bit Holyfield’s other ear. With 10 seconds left in the third round, he was disqualified. His $30 million purse was withheld while Nevada boxing officials reviewed the fight.

Events in Tyson’s life took repeated turns for the worse in the aftermath of the fight, and culminated in his declaring bankruptcy–in part due to $400,000 a year spent on maintaining a flock of pet pigeons–and an arrest for cocaine possession. In 2006, Tyson agreed to join Heidi Fleiss’ legal brothel in Nevada as a prostitute.

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