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On July 14, 2019, Whitaker was crossing the street in Virginia Beach, at the intersection of Northampton Boulevard and Baker Road, when he was struck and killed by a vehicle. He was 55.

In February 2014, Whitaker made national headlines after he evicted his mother, Novella Whitaker, out of the house he purchased for her shortly after he turned pro. Apparently, back taxes were owed on the house and Pernell said that neither his mother nor his siblings, who also stayed in the house, were doing anything to help keep the house afloat financially. Pernell's lawyers said that he is not making the same kind of money as a trainer that he was as a boxer, and needed to sell off the home to satisfy the tax debt owed in order to prevent the property from being seized and put into foreclosure. Outside of the Virginia courtroom where the eviction proceedings took place, Whitaker called the ruling in his favor "a beautiful moment."

Whitaker also became the head trainer of former undisputed welterweight champion Zab Judah, who defeated Kaizer Mabuza in March 2011 to win the vacant IBF welterweight title.

In 2010, Whitaker was inducted into the Hampton Roads Sports Hall of Fame, honoring those who have contributed to sports in southeastern Virginia.

On December 7, 2006, Whitaker was inducted in the International Boxing Hall of Fame along with contemporaries Roberto Durán and Ricardo López. They were all elected in their first year of eligibility.

His first fighter, Dorin Spivey fought matches in 2006. He later trained young prospect Joel Julio.

Whitaker was also the trainer for heavyweight Calvin Brock who, as recently as November 2006, fought for the IBF and IBO titles against Wladimir Klitschko, wherein Brock was knocked out in the 7th round.

In December 2005 Whitaker became a boxing trainer in his home state of Virginia. While the decline of speed and agility pushed him into retirement, his knowledge of the ring and competitive boxing's components led him to seek out up-and-coming boxers to train to fight in the manner in which he did.

In 2002, The Ring ranked Whitaker as the 10th Greatest Fighter of the Last 80 Years.

In June 2002, Whitaker was convicted of cocaine possession after a judge found he violated the terms of a previous sentence by overdosing on cocaine in March.

On February 20, 1999, Whitaker suffered his first convincing defeat against the much bigger, much fresher Félix Trinidad, gamely taking the Puerto Rican the distance in an attempt to win Trinidad's IBF welterweight title. The fight began with both boxers displaying aggressive styles, which included excessive pushing. In the following rounds, both boxers used their jabs most of the time, with Trinidad gaining an advantage when Whitaker attempted to attack inside, eventually scoring a knockdown in round two. In the fourth, fifth and sixth rounds the fighters exchanged combinations. Later in the fight, both boxers fell to the canvas in what were ruled as "accidental slips." In the seventh round, Whitaker displayed more offense, trading power punches with Trinidad, but the champion retained control of the fight's tempo during the eight, ninth and tenth rounds. In the last round, Whitaker, with a badly swollen right eye, displayed a purely defensive stance, avoiding his opponent throughout the round while Trinidad continued on the offensive until the fight concluded. The judges gave the champion scores of 117–111, 118–109 and 118–109.

He met Oscar De La Hoya on April 12, 1997, in Las Vegas, Nevada. Whitaker, defending his WBC championship and the mythical status as the best boxer in the world, pound for pound, succeeded in making De La Hoya look bad through his crafty defense, but he was unable to mount a sufficient offense to convince the judges. Whitaker was awarded an official knockdown in the 9th round and, according to CompuBox stats, outlanded De La Hoya in overall punches and connect percentage, using the jab as his primary weapon; but De La Hoya threw and landed almost twice as many power punches and had a slightly higher power punch connect percentage than Whitaker, which may have been the key factor in De La Hoya winning by a disputed unanimous decision. At the end of the fight, the judges' scores were 111-115, 110-116, 110-116. The fight was a whole lot closer than what the final scorecards showed, and there were many boxing analysts and sportswriters at ringside who felt that Whitaker actually won the fight. It was another controversial decision against Whitaker, but it wasn't seen as a blatant robbery like the Ramirez or Chavez fights.

In his next fight on March 4, 1995, Whitaker added Julio César Vásquez's WBA super welterweight title to his collection. Although Whitaker suffered a flash knockdown early on in the fight, he basically faced no real trouble against Vásquez en route to the win. This was a history making fight for Whitaker, as he became only the fourth fighter in history - joining Thomas Hearns, Sugar Ray Leonard, and Roberto Durán - to have won a legitimate world title in four different weight classes. However, he chose to move back to welterweight.

Whitaker successfully defended his WBC belt against Scotland's Gary Jacobs on August 26, 1995. In January, 1997, Whitaker put his title on the line against Cuban fighter Diosbelys Hurtado. Hurtado gave Whitaker all he could handle and then some. Hurtado had Whitaker down on all the judges scorecards going into the 11th round: Hurtado scored flash knockdowns against Whitaker in rounds 1 and 6, and Whitaker had a point deducted in the 9th round for hitting Hurtado behind the head. But midway in the 11th round, Whitaker landed a left hook that hurt Hurtado and, in a rare display of aggression and power, unleashed a barrage of left-handed power shots, pummeling Hurtado into the ropes, knocking Hurtado out and almost completely out of the ring before referee Arthur Mercante Jr. stopped the fight at the 1:52 mark, giving Whitaker the come-from-behind TKO win. The win set up a showdown with undefeated 1992 Olympic gold medalist Oscar De La Hoya.

Whitaker continued on to dominate for the next few years, defending his welterweight title in a rematch against McGirt on October 1, 1994.

On March 6, 1993, he decisioned Buddy McGirt to become the Lineal and WBC Welterweight Champion.

Whitaker was gaining momentum and boxing experts and fans felt that he needed to win against the pound for pound best boxer in the world: Julio César Chávez. The two met in a welterweight superfight simply named "The Fight" on September 10, 1993 in San Antonio, Texas. In the eyes of many of the spectators, Whitaker outboxed the Mexican legend. However, 2 of the 3 judges saw an even bout with the other judge scoring in favor of Whitaker, resulting in a majority draw. Sports Illustrated featured a cover titled "ROBBED!" after the conclusion of this fight and believed that Whitaker had won 9 of the 12 rounds in the fight. The now defunct Boxing Illustrated magazine, whose editor-in-chief was boxing historian Bert Sugar, had a heading on the cover of its post-fight edition telling readers not to buy the issue if they really believed "The Fight" was a draw.

In 1992, he began his ascent in weight, winning the IBF light welterweight title from Colombian puncher Rafael Pineda on July 18.

Now a champion, Whitaker proceeded to dominate boxing's middle divisions over the first half of the 1990s. In 1990, he defended his Lightweight title against future champion Freddie Pendleton and Super Featherweight Champion Azumah Nelson of Ghana. On August 11, 1990, he knocked out Juan Nazario in one round to win the WBA and vacant lineal lightweight titles, becoming the first Undisputed Lightweight Champion since Roberto Durán. His highlight of 1991 was a win over Jorge Páez and a fight against European Champion Poli Díaz that ended in another win.

Whitaker trudged on, winning a decision over Greg Haugen for the IBF Lightweight title on February 18, 1989, becoming the first boxer to knock Haugen down by sending him to the mat in the sixth round. He then added the vacant WBC & The Ring belts by avenging his loss to Ramirez on August 20.

On March 12, 1988, he challenged José Luis Ramírez for the WBC Lightweight title in Levallois, France. He suffered his first pro defeat when the judges awarded a split decision to Ramirez. The decision was highly controversial, with most feeling that Whitaker had won the fight with something to spare. In his 1999 edition of the 'World Encyclopedia of Boxing,' Harry Mullan stated that the decision in this bout was "generally considered to be a disgrace." To date, the decision is rated at or near the top of many boxing observers' lists of the worst decisions in boxing history.

In just his eleventh and twelfth pro bouts, Whitaker defeated former world champion Alfredo Layne on December 20, 1986 and former WBA and lineal Super Featherweight and WBC Light Welterweight title holder Roger Mayweather on March 28, 1987. Whitaker won both bouts before hometown crowds at the Norfolk Scope, less than a mile from where he lived as a child in a Norfolk housing project. Whitaker would fight nine times in the Scope arena during his career.

Pernell married Rovanda Anthony on December 21, 1985 in the boxing ring at the Virginia Beach Pavilion Convention Center. The couple later divorced. They had four children together: Dominique, the late Pernell Jr., Dantavious, and Devon. Whitaker also had a daughter, Tiara, from a prior relationship.

As an amateur, Whitaker won a silver medal in the lightweight division at the 1982 World Championships, followed by gold at the 1983 Pan American Games and 1984 Olympics. After his retirement in 2001, Whitaker returned to the sport as a trainer. In 2002, The Ring ranked him tenth in their list of "The 100 Greatest Fighters of the Last 80 Years". In 2006, Whitaker was inducted into the International Boxing Hall of Fame, in his first year of eligibility.

Whitaker had an extensive amateur boxing career, having started at the age of nine. He had 214 amateur fights, winning 201, 91 of them by knockouts, though he said that he had up to 500 amateur fights. He lost to two-time Olympic Gold medalist Ángel Herrera Vera at the final of the World Championships 1982 but beat him four other times, notably in the final of the Pan American Games 1983 in Caracas. He crowned his amateur career with an Olympic gold medal in 1984, beating Luis Ortiz to obtain it.

Pernell Whitaker Sr. (January 2, 1964 – July 14, 2019) was an American professional boxer who competed from 1984 to 2001, and subsequently worked as a boxing trainer. He was a four-weight world champion, having won titles at lightweight, light welterweight, welterweight, and light middleweight; the undisputed lightweight title; and the lineal lightweight and welterweight titles. In 1989, Whitaker was named Fighter of the Year by The Ring magazine and the Boxing Writers Association of America. He currently holds the longest unified lightweight championship reign in boxing history at six title defenses. Whitaker is generally regarded as one of the greatest defensive boxers of all-time.

Pernell was born in Norfolk, Virginia on January 2, 1964, the son of Raymond Whitaker Sr. and his wife, Novella. He had two siblings, a brother, Raymond, Jr., and a sister, Monique.

His last fight came on April 27, 2001, against journeyman Carlos Bojorquez. Whitaker, the former lightweight, entered the ring at 155 pounds. He broke his clavicle in round four and was forced to retire; at the time of the stoppage Whitaker was trailing in all the judges' scorecards by 28-29. Following this fight, Whitaker officially announced his retirement. He finished his professional career with an official record of 40-4-1 (17 knockouts).