Baddest men on the planet: The 10 most infamous boxers of all time

The baddest men on the planet: Shocking, sad and often savage, these are the 10 most infamous boxers of all time, including Mike Tyson, Sonny Liston and the Raging Bull himself

  • Boxing is a sport full of colourful and controversial characters
  • Many of its stars are driven by their experiences during horrific childhoods
  • Some have a desire to not only win but to unleash brutality on an opponent
  • And these are the boxers who have gained notoriety above all others 

It takes a certain type of person to step into a boxing ring and risk one’s own life, and that of an opponent, for the sake of entertainment. It is no wonder then that the sport is full of remarkable characters – and many have gone on to find infamy. Often their life stories are full of brutality and tragedy, with their careers inside the ring mirroring the personal turmoil outside of it. These are the boxers who will be remembered among the most notorious of all.

The unmistakable Mike Tyson’s life has been filled with controversy, in and out of the ring

Venezuelan-born Valero perhaps should have never boxed. He was involved in a motorbike accident in 2002 and wasn’t wearing a helmet; he fractured his skull and needed surgery to remove a blood clot. 

As a result, he struggled to gain a license in the US but fought 27 times overall and won every single one by knockout, becoming WBA super featherweight champion and holding the WBC lightweight title. But such aggression did not stay inside the ropes.

In September 2009, he was arrested for assaulting his sister and mother in a family feud in Venezuela but his mother later insisted there was no violence involved.

Six months later he was accused of assault again, by his wife. She needed hospital treatment for a damaged lung but, despite being treated for similar injuries before, later changed her tune to say she had fallen on stairs. Upon visiting her, Valero threatened the medics and his temper was so wild, he was ordered by a Venezuelan court to enter rehab and attend anger-management classes.

A month later, his wife was found stabbed to death and Valero was arrested, where he reportedly admitted to the murder. A day later, he was found hanged in his prison cell.

‘I asked the authorities not to let him out. He needed a lot of help. He was very bad in the head,’ his manager Jose Castillo told reporters. ‘But they let him out. They were very permissive with him and because of that, we’re now in the middle of this tragedy.’

Edwin Valero (left) lands a punch on Antonio DeMarco during his win in February 2010.

The Venezuelan was an aggressive fighter and became a super featherweight world champion – but he was arrested for the murder of his wife and later killed himself while in prison

Sonny Liston

At the age of 20, Charles ‘Sonny’ Liston was sent to prison for five-and-a-half years at the Missouri State Penitentiary for armed robbery.

He endured a tough upbringing – the 24th of 25 children in a household so poor that he was sent to work at the age of eight. He claimed not to know what year he was born while his father, Liston said, only ever gave him a beating.

It was behind bars that he was introduced to boxing, with Reverend Alois Stevens suggesting he entered the ring for a sparring session with heavyweight Thurman Wilson. 

It lasted two rounds. ‘Get me out of this ring,’ Wilson is alleged to have said. ‘He is going to kill me!’.

Sonny Liston overcame a tough childhood to leave a big mark on heavyweight boxing history

Liston turned professional in 1953 and went on to have a remarkable career, becoming heavyweight champion of the world in 1962 with a first-round knockout of Floyd Patterson, a feat he repeated a year later.

His career was punctuated by run-ins with police. In 1956, he reacted to being stopped on the street by punching a policeman and stealing his gun, for which he served nine months inside.

But he made it back out, and made it back to the ring. Most famously he was beaten by Cassius Clay (Muhammad Ali) in 1964. They had a rematch a year later and Ali knocked him out in the first round.

Liston’s death, in December 1970, is shrouded in mystery. He was reportedly discovered near a balloon with heroin in it, and his arm covered in needle marks. Yet he apparently had a fear of needles and in 2013, a man came forward claiming to be the son of the mafia hit-man who killed him.

Liston lands a heavy right hand on the jaw of Muhammad Ali – then Cassius Clay – in 1965

He was a brutal puncher but his own KO by Ali gave boxing one of its most famous pictures

Roberto Duran

‘I was Mike Tyson before Mike Tyson came along,’ Duran wrote in his autobiography. ‘Fighters would take one look at me and crap in their pants. “El Diablo”, they called me: “The Devil”.’ 

Duran was a brutal lightweight, arguably the best and most dangerous in boxing’s history, and moved up to welterweight, light middleweight and middleweight, winning titles in each.

Duran loved fighting. He didn’t retire until he was 50 years old, in 2002. He fought a total of 119 times, winning 103 with 70 coming via a knockout.

His most famous fights were his three against Sugar Ray Leonard. Duran won the first in Canada in 1980 but was defeated the next two times, the rematch later that year renowned in boxing history as the ‘no mas’ bout.

The match was ended in the final moments of the eighth because Duran apparently said ‘no mas’ to referee Octavio Meyran – which means ‘no more’ in Spanish. Duran insisted he never said he wanted to quit and was taunted by Leonard post fight.

‘I made him quit’, Leonard said. ‘To make Roberto Duran quit, was better than knocking him out.’ 

Duran later said he quit because he was struggling with stomach cramps, but even his manager rejected that and said it was because he was losing the fight so dramatically.  

Duran lost the decider in 1989.

Roberto Duran (right) cracks the jaw of Iran Barkley during a fight in Atlantic City in 1989

His fighting style was ultra-aggressive and he earned the nickname ‘The Devil’

He had famous fights against Marvin Hagler (above), Sugar Ray Leonard and Tommy Hearns

Mike Tyson

There was nothing like Mike Tyson when he burst onto the heavyweight scene in 1985 at the age of 18. Tyson was boxing’s youngest ever heavyweight champion at 20 when he defeated Trevor Berbick. He won 26 of his first 28 fights by knockout and out of his 50 career wins 44 were by KO. 

His aggression, his speed and his power left opponents scared of Tyson before they even entered the ring – look at his fight with Michael Spinks in 1988.

Yet his nickname ‘The Baddest Man on the Planet’ wasn’t just because of how powerful he was in the ring. 

Tyson infamously bit part of Evander Holyfield’s ear off in the third round of their 1997 rematch. He was disqualified, having already been deducted two points for biting Holyfield’s other ear. Tyson claimed his action was a retaliation to Holyfield repeatedly headbutting him without being sanctioned.

Away from boxing, Tyson was sent to prison in 1992 for six years after being found guilty of rape. He served three years and was released in March 1995. Tyson converted to Islam during his time in prison.

It was during his time in prison that Tyson discovered a way to own a tiger.

He explained on Joe Rogan’s podcast in January: ‘So I’m in prison, I’m talking to my car dealer at the time and he has some cars that belong to a [mutual friend], and he’s discussing, “If he doesn’t pay for these cars, I’m going to sell these cars to somebody and get some horses.”‘

“I said, “What, you can get horses? And trade horses in for cars?” Because I had a lot of cars, I’d probably get some horses too. And he said, “Yeah man, you can get cougars, lions, tigers…” I said, “You do?! Can you get me some tigers?”

‘And I’m a young guy. I’m saying to myself, “Wow, that would be cool. Get me some cubs, man”.’

Tyson knocks out Trevor Berbick to become youngest heavyweight world champion in history

His behaviour out of the ring was often odd – such as owning a pet tiger – and sometimes awful

His infamy inside the ring was sealed when he bit a chunk out of Evander Holyfield’s ear

Antonio Margarito

Mexican-American boxer Antonio Margarito lost his license in 2009 when his hand wraps failed a pre-match inspection before his fight with Shane Mosley. 

They contained gypsum, a chemical which, when combined with sweat or moisture, forms plaster that is used to make casts. At a hearing, Margarito insisted he did not know what was in his wraps and it had been an error by his trainer, Javier Capetillo.

Later that year, the LA Times said stains on Margarito’s wraps were similar to ones in his fight prior to Mosley, where he beat Miguel Cotto. Cotto’s father was quoted as saying the photos of the wraps are ‘overwhelming’ evidence that Margarito beat his son with loaded wraps.

Antonio Margarito’s hand wraps were despicably loaded with chemicals to harden them

He has also been accused of beating Miguel Cotto in 2008 (above) with hardened wraps

Floyd Mayweather

Unquestionably one of the best pound-for-pound boxers in history, Floyd Mayweather Jnr’s 50-0 record is imperious. 

But outside of the ropes Mayweather’s life is not as clean his fight history and he has fallen on the wrong side of the law many times.

In 2002, he received a six-month suspended sentence for domestic violence and two years later was ordered to undergo counselling for ‘impulse control’ after two counts of misdemeanour battery against two women. In 2005, he was given a 90-day suspended sentence for hitting and kicking a bouncer. 

In 2012, Mayweather went to prison for attacking Josie Harris, the mother of his three children. He was released that August.

Mayweather did not have a straightforward upbringing. His father was sent to prison in 1992 for drug trafficking while his mother was a heroin addict.

‘Boxing is easy but life has never been easy.’ Mayweather told the Independent in 2007. ‘I had a father who was a hustler and a mother who was on drugs. I was the man in the house from 16. That’s just the way it was.

‘At Christmas we never had a Christmas. My mother would go out and steal presents for me.’

There is no need for Mayweather to steal anything now. Nicknamed ‘Money Man’, he often flouts wads of cash on social media and according to Forbes has an estimated wealth of $560m (£424m).

Floyd Mayweather’s ostentatious displays are crass – but he has plenty to boast about 

He flattens Ricky Hatton in 2007, just one of his 50 victories during an undefeated career 

Mayweather, who has a history of beating women, poses with OJ Simpson in 2001

Rubin Carter

A man whose life is defined by a murder conviction that was twice overturned amid claims of racial prejudice. Rubin Carter served almost 20 years for a crime he always maintained he didn’t commit. But while he may not have been a murderer, he was still a nasty guy to encounter.

Carter was sent to a reformatory aged 11 for stabbing a man ‘everywhere but the bottom of his feet’. He claimed the man had tried to molest him.

After a spell in the army ended, Carter was sent to prison for assaulting an elderly woman. He entered into the world boxing upon his release in 1961 as a middleweight, earning the nickname ‘Hurricane’ for how quickly he could knock people out.

Carter was sent to prison in 1967 for a triple murder at a bar in New Jersey but always fiercely protested his innocence. The case caught the attention of Bob Dylan, who wrote his 1975 song ‘Hurricane’ about Carter.

He was freed in 1976 for nine months before returning behind bars at a retrial. In that time, he was subject of a $1million lawsuit from an associate, Carolyn Kelley, who had helped him win a retrial. 

She claimed he beat her unconscious as she tried to solve a discrepancy over a bill for a hotel room.

She once described his flash of temper to The Washington Times: ‘You know how a snake is crawling on the ground and suddenly half of his body is up in the air and his tongue is sticking out, wiggling, wiggling, wiggling, and his eyes are closed almost shut?’

Carter was released once again in 1985 and moved to Canada, where he died in 2004. The murders in the New Jersey bar have never been solved. 

Rubin ‘Hurricane’ Carter (right) unleashes on Holly Mims at Madison Square Garden in 1962

Carter was sent to prison in 1967 for a triple murder in New Jersey, but he protested innocence

Bob Dylan immortalised Carter’s story with his protest song ‘Hurricane’, released in 1975

Andrew Golota 

The Polish heavyweight is most commonly remembered for his fight against Riddick Bowe in 1996 at Madison Square Garden. 

It was clear in the early exchanges that Golota had the upper hand against Bowe but his punches kept wandering low. In the seventh round, the Pole had points deducted for the third time over it before a (legal) combo had Bowe wobbling.

But then, inexplicably, Golota went low again and referee Wayne Kelly disqualified him, which in turn sparked a mass brawl.

Policeman and spectators were injured in the ensuing melee, while Golota himself was left needed 11 stitches after being hit with a radio by one of Bowe’s entourage. 

They had a rematch that same year and Golota was again disqualified for hideous low blows. 

Polish heavyweight Andrew Golota was involved in two of boxing’s most infamous fights

Twice he was disqualified against Riddick Bowe for hitting him with sickening low blows

Johnny Tapia

Tapia had a tattoo across his stomach reading ‘Mi Vida Loca’ – my crazy life. Born in New Mexico, Tapia had a tough start. His father was murdered before he was born and at the age of eight, he witnessed his mother being kidnapped. She was raped, stabbed and left for dead and passed away four days later.

Tapia was then raised by his grandmother and found boxing at the age of nine, but turned to drugs as a teenager. In his younger years, it didn’t derail his career. As an amateur, he had a ferocious record of 150 wins and 12 defeats.  

He developed into an immensely talented pugilist and became a five-time world champions across three weight divisions. He won IBF and WBO super flyweight titles between 1994 and 1998, unified the WBA and WBO bantamweight titles between 1998 and 2000 and in 2002, claimed the IBF featherweight title.

His most famous rivalry was with Danny Romero – whose father had once trained both boxers. 

But his boxing career – and life – was one blighted by addiction. In October 1990, he was banned for three years for testing positive for cocaine. 

In 2003, Tapia spent six months in rehab after collapsing at home and saying he had become addicted to prescription pills. 

Four years later, by which time he was a five-time world champion, he was hospitalised after being found not breathing in his hotel room where bags of cocaine were found. 

Tapia died in 2012, of heart failure.

Boxing promoter Lou DiBella said in a 2015 boxing documentary about Tapia: ‘He knew he wasn’t destined to be around for a long time.

‘Poor kids fight. Usually people are fighting their way out of something. They fight their way out the streets. They fight their way out of gang life. They fight their way out of addiction. Johnny fought through all of these things while he was winning world championships.’ 

Johnny Tapia aims a right hand at Marco Antonio Barrera in Las Vegas in 2002

The flamboyant Tapia became a five-time featherweight world champion

His ‘crazy life’, which included drug abuse, caught up with him and he died at the age of 45

Jake LaMotta

LaMotta fought for money from the age of just eight. He’d scrap with other kids in his neighbourhood and onlookers would throw change at them, which his father would use to pay rent and bills.

He became a professional boxer in 1941 at the age of 19, having learnt to box in a reformatory after being sent there for an attempted robbery. As a pro, he fought Sugar Ray Robinson five times but won only once.

La Motta was never worried about getting hit and learnt to absorb an extraordinary amount of power and force from his opponents. He would often stand within striking range of his foes in order to increase his own chances of landing a big punch. He became known for having one of the strongest chins in boxing.

But LaMotta’s fight with Billy Fox took on a more sinister tone. He was knocked out in the fourth round but amid concerns that the fight was fixed, the New York State Athletic State Comission held back the purse and LaMotta was suspended.

LaMotta later admitted throwing the fight due to influence from the mafia. 

In his life post-boxing, he owned bars and became a comedian. But in 1958 he was arrested for introducing men to underage women and was sent to prison for six months. 

His memoir, Raging Bull, inspired the film of the same name directed by Martin Scorsese and starring Robert De Niro. 

Jake La Motta was an extraordinary middleweight, who went on to find wider fame after Robert De Niro (right) played him in the celebrated film about his life, Raging Bull

LaMotta lands a right to the body of Bob Satterfield at Wrigley Field in Chicago in 1946

LaMotta became known for his ability to withstand an extraordinary amount of punishment; here he gropes for the ropes in the final seconds of his loss to Sugar Ray Robinson in 1951

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