BOXING has seen plenty of bad boys inside and outside the ring.
Over the decades some of the sport’s biggest stars have brushed up against the law – and a few have even ended up doing jail time.
Here are boxing’s top 10 bad boys outside the ring.
Edwin Valero
Edwin Valero competed in the super featherweight division from 2002 to 2010.
The Venezuelan was enjoying a solid career, winning all of his 27 fights by way of knockout.
In February 2010, he soundly knocked out the talented Antonio DeMarco in nine rounds, in what would eventually be his final fight.
Shortly after, the 28-year-old was arrested and forced to undergo psychiatric treatment for abusing his wife.
Two months later after being released he stabbed her to death in a hotel room in Valencia, Venezuela.
Valero hanged himself in his jail cell the following day.
Pernell Whitaker
From 1984 to 2001, Pernell Whitaker competed in four different weight divisions: lightweight, light welterweight, welterweight and light middleweight.
He won world titles in all four divisions and fought boxing legends such as Oscar De La Hoya and Julio Cesar Chavez.
In 1989, Whitaker was named Fighter of the Year by Ring Magazine.
However, later in his career Whitaker struggled to stay motivated and fell into substance abuse.
In 1998, he tested positive for cocaine following a fight with Andrey Prestryaev – and was later charged with possession of a controlled substances after cocaine was found in his car during a traffic stop.
He only served four days in jail, but in the years since he has been charged with five further traffic violations, including drunk driving.
Sonny Liston
Sonny Liston was a stunning heavyweight, even though he is probably best remembered for his two defeats to Mohammad Ali in 1964 and 1965.
He had only lost four times prior to his bouts with Ali, and had a record of 50 wins.
Liston fought in the heavyweight division from 1953 to 1970.
However, he also had some troubles with the law, starting when he was a youth growing up in a St. Louis.
Over the course of his life, he was arrested 19 times for crimes ranging from armed robbery to assaulting a police officer.
In 1950, Liston was convicted of two counts of armed robbery. He was released on parole after serving two years in prison.
In 1956 and 1958, he assaulted a police officer and was forced to flee St. Louis and to refuge in Philadelphia.
Charles “Kid” McCoy
Charles McCoy was a crafty fighter who recorded a then-record 81 fights in his career, with 55 wins coming by knockout.
He competed under the middleweight division from 1891 to 1912.
However, McCoy’s career took a turn when he decided to pursue an acting career and moved to California.
His short-lived on-screen career and an alcohol addiction left him broke.
He became involved in an affair with a wealthy married women who was killed by a gunshot to the head.
The following day, McCoy held 12 people captive at a local store during a robbery.
He was caught and later convicted of manslaughter, serving prison time for eight years until his parole in 1932.
Bernard Hopkins
According to an article published by the New York Times, Bernard Hopkins began smoking pot at age 11, started robbing by age 13, had been stabbed by age 14 and by the time he was 17 had served time behind bars.
He was convicted of strong-arm robbery and assault before he was old enough to buy a pack of cigarettes.
At the age of 17, he was sentenced to 18 years in Graterford State Penitentiary for nine felonies, including armed robbery.
He was released after five years in 1988.
Remarkably, he went on to have a successful boxing career, going 55-8 in his career.
Hopkins fought under the middleweight and light heavyweight division from 1988 to 2016.
On May 21, 2011, at the age of 46, Hopkins became the oldest fighter to win a major world championship title.
Adrien Broner
At 31-years-old, Adrien Broner had enjoyed an impressive career winning 33 fights and losing only four.
The talented fighter currently competes in four different divisions at super featherweight, lightweight, light welterweight and welterweight.
However, in 2018, he was charged with gross sexual imposition, a fourth-degree felony, misdemeanor sexual imposition and abduction, a third-degree felony.
A 35-year-old women alleged that he sexually assaulted her in a nightclub.
In 2019, Broner pleaded guilty to assault and unlawful restraint, both misdemeanors. He was given two years probation for his actions.
In March 2020, Broner was arrested in Miami following a drunk driving incident and was sentenced to seven day in Cuyahoga County jail for violating his probation connected to his 2018 assault case.
Floyd Mayweather Sr
Floyd Mayweather Sr competed in the welterweight division from 1974 to 1990 and had a professional record of 28 wins and six losses.
From 1987 to 1992, Mayweather Sr smuggled cocaine into the United States in detergent boxes.
In 1993, he was caught and charged with drug trafficking and served three of a five-year prison sentence.
Floyd Mayweather Jr
Like father, like son.
In 2012, Floyd Mayweather Jr reported to a Las Vegas County jail to begin serving a 90-day sentence on charges of domestic violence for attacking his ex-girlfriend, Josey Harris.
During his two months behind bars, he repeatedly wrote to prison officials about his treatment.
“There is 7 days in a week and I only get five hours out of my cell and that’s unfair,” Mayweather complained. “This is my third time writing asking to be moved.
“My mind is not the same. I’ve lost weight I am stress out I can’t workout and I need some type of exercise.”
The undefeated Mayweather competed in five different weight classes from 1996 to 2017 at super featherweight, lightweight, light welterweight, welterweight and light middleweight.
He retired from the sport of boxing with a 49-0 record.
Mike Tyson
At the high of his career, The Baddest Man on the Planet found himself on the wrong side of a judge.
In 1992, Mike Tyson was convicted for the rape of Desiree Washington and was sentenced to six years in prison.
Tyson reached the realms of boxing glory at a young age, becoming the youngest fighter ever to simultaneously hold all three world heavyweight titles at 20-years-old.
He held all three titles for some time until 1990, when he was beaten in the tenth round by knockout against James Douglas.
After only serving three years of his prison sentence, Tyson returned to the ring and regained one belt until his career began its descent in 1997 after a fight against Evander Holyfield.
He was also charged with assault in addition to three separate incidents involving alleged sexual harassment and sexual abuse, but he was not convicted.
Tyson competed in the heavyweight division from 1985 to 2005, he announced his comeback earlier this year.
Jack Johnson
Jack Johnson’s time in prison was vastly different from the other boxers on this list.
He was the first African-American world heavyweight champion and defied the odds to rise to glory in the early 20th century when segregation was still a way of life.
Johnson competed in the heavyweight division from 1897 to 1931.
His refusal to bow to segregation made him a sporting icon amongst many Americans, but it also made him a target for those in power.
In 1920, Johnson was convicted of violating the Mann Act.
He was found guilty by an all-white jury of being part of a prostitution ring, with the prosecution saying he had transported a woman across state lines for immoral purposes.
In reality, Johnson had bought a train ticket from Pittsburgh to Chicago for his white girlfriend.
Johnson spent one year in prison.
His conviction was regarded by most as a gross miscarriage of justice and in 2018 President Donald Trump pardoned the fighter for the “racially motivated injustice.”
