Reggie Gross was a boxer turned gangster who Mike Tyson knocked out and is now serving 60 years in prison for triple homicide

One of Mike Tyson’s most spectacular early knockouts came at the end of an exciting one-round battle with Reggie Gross – a hitman and mob enforcer now serving life in prison in South Carolina.

Gross lasted less than three minutes in the ring with Tyson in 1986 but he made an impression on the 19-year-old phenomenon, coming out firing and catching Tyson with a terrific uppercut. Unfortunately for Gross, exchanging firepower with a young Tyson was a dangerous game and ‘Kid Dynamite’, ducked under the taller man’s blows and sprung up to land a savage left hook which put Gross down.

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Tyson beat Gross in one round and five months later became the youngest heavyweight champion in history

Beforehand, Tyson was aware that ‘Rugged Reggie’ could be more dangerous than his 18-4 (12 KOs) record suggested – he had a reputation for ruining the unbeaten records of heavyweight prospects. “He was a tough fighter they called ‘the Spoiler’ because he had upset some good fighters, including Bert Cooper and Jimmy Clark, who was a great American Olympian,” Tyson said later.

What Tyson may not have known was that as well as being a talented if underachieving boxer, Gross was also an enforcer for a violent drug gang in his native Baltimore. Just three months after his fight with Tyson on HBO, Gross committed the first of three brutal murders he would eventually be convicted of carrying out as contract killings.

Much like Tyson, whose early life on the streets of Brooklyn was no picnic, Gross had a tough upbringing. His father was stabbed to death on the streets when Reggie was only three days old and by the age of only 13, Gross was in juvenile detention following a purse snatching carried out with what turned out to be a toy gun.

Like many troubled teens, Gross found boxing and discovered he had an aptitude for it. He was 6ft 3in, athletic, could punch, and after a 22-fight amateur career he turned pro in 1982. Under the guidance of respected trainer Mack Lewis, Gross racked up a 14-0 record, initially at light-heavyweight, including a win over future world champion ‘Prince’ Charles Williams.

However Gross was living a double life away from the boxing gym. He was using drugs and had become involved with one of the deadliest and most notorious gangs in Baltimore, headed by Warren ‘Black’ Boardley. The kingpin of a major cocaine-heroin trafficking group, Boardley had boxed himself.

Gross’s drug addiction and the tragic death of his five-year-old son in a house fire understandably affected his boxing career. At the same time a Cus D’Amato-guided Tyson was rising in prominence, Gross lost four of eight fights between 1984 and 1986.

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Tyson was moulded into a champion by Cus D’Amato, who died a year before he won the title in 1986

However he knew that when was matched with Tyson at Madison Square Garden in June ’86 that one win against the hottest heavyweight prospect in decades could turn everything around for him. Gross got himself in career-best shape.

“Mike Tyson is like a bull, he comes right at you – I eat bulls for dinner,” said a confident Gross pre-fight. Even in the abbreviated contest, Gross shows some skill and hand speed, firing out a jab and catching Tyson when he unleashed a flurry of punches. Unfortunately when facing Tyson – who later that year would become the youngest heavyweight champion in history – you needed either supreme defensive skills or a cast-iron jaw.

Gross got carried away landing his own shots and Tyson’s compact left hook flattened him. Reggie bravely got up but on shaky legs and Tyson’s salvo of follow-up hooks sent him slumping into the ropes. The fight was called off with 24 seconds left in the first round as the MSG went wild.

Reggie admits that he got carried away after catching Tyson cleanly. “I say to myself: ‘Oh my God, I hit him,’” Gross recalled, years after the contest. “I hit that man on the chin. I say: ‘Suppose I hit him one more time with this right hand. I’m gonna knock his block off.’”

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Despite being knocked down twice by Tyson and being out on his feet, Gross wanted to continue the fight

Tyson, the man who instead knocked-off Reggie’s block, later reflected: “He decided to start trading punches which was fine with me… I knocked him down with a vicious left hook and then knocked him down for a second time with a succession of punches. The ref stopped the fight because Gross was glassy-eyed, but Reggie complained. ‘You can’t even walk but you want to fight?’ the ref said.”

The win took a teenage Tyson to 22-0 (20 KOs) but Gross was soon on a far darker path. Later that year, Baltimore homicide detectives arrested him in connection with the killing of a rival of Warren Boardley’s gang, a street dealer named Andre Coxson.

Eyewitness reports said Coxson was shot once in the upper body, then the gunman stood over him and fired several shots into his head. In other words, this wasn’t just a case of random street violence, but a deliberate and professional hit.

“It had all the signs of an execution,” said Baltimore homicide detective Mark Tomlin, “especially with the shooter standing over the man and finishing him off with two shots to the head.”

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Gross’s life of crime eventually caught up with him and was undone by an FBI informant

Gross was arrested for the killing. But, despite the fact the state produced several eye witnesses who said they saw him carry out the murder then flee down an alley, he was found not guilty by a jury. The boxer had spent much of his career-high purse for the Tyson fight, a reported $50,000, on legal fees.

At least he was free to resume his boxing career. Now cast firmly in the ‘opponent’ role, Gross would lose in eight rounds to Frank Bruno in 1987 and his last fight actually came on a Tyson undercard. While ‘Iron Mike’ was securing his greatest win, knocking out Michael Spinks in 91 seconds in June 1988, Gross was stopped by big-punching Donovan ‘Razor’ Ruddock (himself a future Tyson opponent).

Yet being cut down to size by Ruddock soon became the least of Gross’s problems. Donnie Andrews, a criminal turned FBI informant – and the inspiration for Omar Little on the TV series ‘The Wire’ – was recording conversations on the inside of the Boardley gang. Including chats with Gross which implicated him not only in the murder of Coxson, but also in using a sub-machine-gun to kill two other mid-level drug dealers from rival gangs. Three of at least 10 murders the FBI found the Boardley gang had carried out.

Gross was alleged to have been paid $3,000 for each hit, mere months after he’d headlined the MSG with Mike Tyson. The boxer pleaded guilty to the charges in the summer of 1989, saying: “At the time, I was addicted to heroin… I made some huge mistakes. I can’t change the past, but I can do better in the future. I know that I will be going away [for] a long while. I just pray that it will not be for the rest of my life.”

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Gross lost to Ruddock in 1988 on the night Tyson demolished Spinks – but this was the least of his concerns

However judge Paul Niemeyer sentenced Gross to three life terms, saying: “You fell from a most promising career as a boxer. Unfortunately, you elected a life in which you would pursue some of the most brutal crimes.”

Gross, who later claimed he did not carry out the killings, is 60 now and in jail. His stated release date is 2048, by which time he will be 86. Unlike Tyson, who eventually overcame a harsh upbringing and a life filled with violence and heartbreak to find some peace at age 56, Reggie Gross is a tragic example of the fact that boxing cannot save all of the troubled individuals who set foot in the ring.