Whitaker was born in nearby Norfolk, Virgnia, where he began his amateur career. Before turning pro, Whitaker was one of the best amateurs in the world, taking silver at the 1982 World Championships, avenging that defeat a year later by beating two-time Olympic gold medalist Ángel Herrera Vera for the gold at the 1983 Pan American Games, and winning Olympic gold in 1984. By 1987 the young Whitaker had already beaten a couple former champs, earning comfortable decisions over Alfredo Layne and Roger Mayweather. He got his first title shot a year later against José Luis Ramírez.
Boxing heads consider Ramírez’s split-decision win over Whitaker one of the most egregious robberies in the history of the sport, though Whitaker at least got his revenge quickly. Whitaker soundly beat Ramírez in the rematch to win the WBC lightweight championship belt, and by 1990, he was the undisputed lightweight champion of the world. He reigned as boxing’s pound-for-pound king for years.
Less than half of Whitaker’s wins came by knockout. That stat, unusual for such an elite boxer, reflects Whitaker’s abilities as one of the greatest defensive boxers of all time. Few fighters have ever been harder to hit. This highlight reel of him slipping and dodging is an immensely satisfying display of the elusive Whitaker’s skills.
Whitaker went on to win titles in three other weight classes on an undefeated run that lasted until he lost another controversial decision to Oscar De La Hoya despite dropping De La Hoya for the first time in his career. Perhaps because he was not a particularly hard puncher, Whitaker was on the wrong end of three of boxing’s most vexing decisions, with a baffling 1993 draw against then-undefeated Julio César Chávez sandwiched between the Ramírez and De La Hoya losses. The injustice of the Chávez decision famously made the cover of Sports Illustrated under the simple headline “ROBBED!”
Whitaker ended his career with a loss against the much larger Félix Trinidad before getting his collarbone broken by Carlos Bojorquez in a 2001 bout. After his retirement, Whitaker worked as a trainer in Virginia Beach and served a few stints in prison on drug charges. He was inducted into the boxing Hall of Fame in 2006. “He was this person who was only comfortable in the ring,” Main Events promoter Kathy Duva told ESPN. “He had demons, but when he was in the ring, that was when he was in control and when he was happy and when he was the very best at what he did, and he wanted to show that to everybody.”