extraordinary Trevor Berbick fought Mike Tyson, Muhammad Ali and Larry Holmes, but troubled heavyweight put a gun to his manager’s head, spent time in prison and met a tragic end

Trevor Berbick is the only boxer to fight Muhammad Ali, Larry Holmes and Mike Tyson – yet the heavyweight’s life outside the ring was even more extraordinary and ended with his grisly murder at the hands of his own nephew.

Jamaican Berbick was the last man to fight Ali and the first world title challenger to take Holmes the distance. But Berbick is best known for unwittingly lighting the fuse on the Tyson era when he lost his world championship to the 20-year-old in the most replayed and rewatched of all ‘Iron Mike’s legendary KOs.

But before he became a stumbling, modern-day meme, Berbick was an unlikely heavyweight contender. He only had 11 amateur fights before turning pro in 1976 and even his age was shrouded in mystery, as he was variously reported to be either three years younger or four years older than his official date of birth

“Legally, I’m a spirit – I have no age,” Berbick explained; a line every 16-year-old has tried at least once while trying to get served.

Physically, he looked the part: over 6ft 2in, broad and muscular. But Berbick was rugged and awkward rather than explosive or skilful. Fighting out of Canada, he lost his 12th pro fight but later upset ‘Big’ John Tate to earn a shot at Holmes. The ‘Easton Assassin’ was on an eight-fight KO streak but Berbick lasted the full 15 rounds – although the most famous encounter between the pair came later: when Holmes ran over the top of a limousine and drop-kicked Berbick, WWE-style, in the middle of a car park.

Berbick’s in-ring showing against Holmes earned him the opponent role for Ali’s ill-advised final comeback in 1981. A flat, flabby, 39-year-old Ali was already feeling the effects of his brutally hard career and simply should not have been in the ring. The fight took place in a decaying baseball stadium in Bahamas, boxers on the card had to share two pairs of gloves, while a cowbell was used to toll rounds. Berbick outworked ‘The Greatest’ over 10 rounds but the tawdry sideshow earned him few new fans.

Instead, the biggest victory of Berbick’s career came five years later. The 6-1 underdog shocked the gifted but erratic Pinklon Thomas – one of the ‘lost era’ of 1980s American heavyweights who struggled with addictions – to win the WBC version of the title.

That put him in the sights of Tyson, who was aiming to become the youngest ever world heavyweight champ. Berbick was paid a career-high $2.1million to face ‘Kid Dynamite’ and did his best to unsettle the challenger pre-fight. Knowing Tyson liked the stripped-down black shorts look, Berbick wore black himself – meaning Tyson, as challenger, would need to change. (Trevor’s knee-high socks were worn for reasons only he knew.)

Instead, Tyson wore black to, and just swallowed the $5,000 fine for the kit clash. The bout was billed as ‘Judgement Day’ but only one man was a convincing Terminator. Berbick had a size advantage over Tyson but he was slower, clumsier and lacked the mobility to give the young phenomenon problems.

As if that wasn’t enough, Tyson later revealed that when special guest Ali was introduced to the crowd pre-fight, he turned to Tyson and said: “Kick his ass for me” (Mike may have been paraphrasing). Now Tyson was 'angry and looking for revenge' over a man who had beaten one of his heavyweight idols growing up.

Berbick survived the first round without going down but was wobbled badly before the bell. In a show of bravado he leered at Tyson and jutted his chin out before going back to his corner.

Tyson didn’t need to be invited twice. The second round featured the remarkable feat of Tyson knocking down Berbick three times with one punch. Following a ferocious barrage, Tyson clobbered the champion with a chopping left hook. After a brief delay Berbick went down, got up, fell into the ropes, got up for a second time, then staggered across the ring and collapsed again like a discount deckchair.

His brain and legs were simply no longer in communication and referee Mills Lane waved the fight off. Tyson was a world champion and Berbick had earned himself top spot on future highlight reels of ‘The Baddest Man on the Planet’s most spectacular KOs.

Berbick kept fighting with diminishing success, while the defeat to Tyson marked a slide in his fortunes outside the ropes. In 1991, a suited Berbick interrupted a Holmes post-fight press conference to bizarrely accuse Larry of sending a sex worker, 'Jenny from Jacksonville', to his room the night before they fought to distract him. He offered Holmes a street fight and duly got one later on when the heavyweights had that car park brawl.

In the same year, Berbick took part in a ‘boxer vs wrestler’ match against the legendary Nobuhiko Takada in Japan. Except there was confusion over what exactly the rules were and when he found out he could be kicked below the belt, Berbick moaned to the referee, then left the ring and forfeited the contest. What a heel move.

More serious criminal setbacks followed. Berbick was regularly in trouble with the law: he was once convicted of assault after he put a gun to a former manager’s head and demanded money he claimed he was owed. But it took an even nastier turn in 1992 when he was found guilty of sexually assaulting his family’s babysitter – Berbick argued it was consensual – and spent 15 months in jail in Florida.

He was deported to Canada, then eventually back to Jamaica, although his boxing career lasted until 2000. A CAT scan revealed blood clots on his brain, eventually forcing Berbick’s retirement with a record of 49 wins (33 KOs), 11 losses and a draw.

There was to be no peace in retirement, however. Six years later, Berbick was found dead in a churchyard in Portland, Jamaica, with what was described as a vicious ‘chop wound’ that had split his skull open. Police declared it a homicide and arrested two men – one of them Berbick’s 20-year-old nephew, Harold Berbick – for the crime.

He had apparently been involved in a land dispute with his uncle, and Harold and his accomplice were accused of jumping the ex-boxer with a metal pipe and a crowbar while he was on his way home from a party. Berbick had died almost instantly and his two attackers were duly convicted, his nephew receiving a life sentence for murder.

A bloody, brutal end to an unremarkable boxer who lived a remarkable life. “We have our challenges in life but Trevor seemed to handle his very badly,” understated his friend C Lloyd Allen, a former president of the Jamaica Boxing Board. “Once he lost to Tyson, he just went down a slippery slope.”