“SOMEBODY wins and somebody loses,” wrote W.C. Heinz in The Professional. “There’s as much of a story in a fighter losing as in a fighter winning, maybe more.’

This is the story of Roman Greenberg and it begins with a futile Facebook search: R-O-M-A-N. G-R-E-E-N-B-E-R-G.

Cedric Boswell, an old acquaintance, tried spelling the name myriad ways, had a root around Instagram for good measure, but could find no trace of Greenberg’s existence. Resigned to failure, the American heavyweight then began thinking how unusual it was for a man in his thirties to eschew any form of social media presence and replaced initial curiosity with a greater concern for his wellbeing. He hoped he was doing okay.

“I always wondered what happened to him,” Boswell told Boxing News. “Couldn’t help it.”

The last time Boswell saw Greenberg it was August 2008 and he was slumped against the ropes of an Atlanta boxing ring having received a series of unanswered punches to the face. They were thrown by Boswell, thrown without a modicum of concern for Greenberg’s wellbeing, and designed to get him out of there. Out of his way. Out of the ring. Out of the heavyweight rankings. They were designed to erase him.

Before that moment, Roman Greenberg was undefeated in 27 pro fights and seemingly on course to crack America and cash in on his Jewish heritage and no shortage of skill. Jews believed he was destined to become their first world heavyweight champion [Max Baer held the belt in 1934 but historians claim Baer was only a quarter Jewish], excitable promoters tipped him to become boxing’s first “billionaire heavyweight”, and Angelo Dundee, upon watching him train, was reported to have labelled him the fastest heavyweight he’d seen since Muhammad Ali.

Greenberg was in on it as well. Fifteen years ago, fuelled by this fervour, he was sitting ringside at York Hall, Bethnal Green in a long, black Matrix-like leather jacket regaling me with his plans to become European heavyweight champion in 2004 and then “go on to world titles”. He was just 21. “I think there is a good possibility that will happen,” he added, confidently, “and that is what we are all working towards.”

When he said “we” it was meant in the team sense. He ensured every member of this team – his “we” – was correctly jotted down in my notepad, an indelible memory from that night in the East End, and emphasised their importance. There was Robert Waterman, his promoter, and Jim Evans, David Porat and Steve Bernath, his trainers, all of whom took care of Roman when he’d arrive in Maidenhead five or six weeks before a scheduled fight. “My career has gone brilliantly so far,” Roman said. “I couldn’t be happier. Those guys are all doing their job, and I just have to do mine.”

For Greenberg, a man whose family left the former Soviet Union for Vienna, Austria when he was six, only to then move to Israel four years later, a boxing ring was always a symbol of consistency, while trips to England offered the chance to spread his wings and escape a country that made his family wait two years for citizenship. “Without citizenship, you have no rights, nothing,” he said.

Born in Moldova, Greenberg, encouraged by his father, took up boxing at 11, won silver medals for Israel at the European and World junior championships, but saw a 2004 Olympic dream dashed on account of the Israeli sports authorities’ refusal to provide enough financial support. Waterman, the promoter who befriended a 16-year-old Greenberg in Tel-Aviv in 1998, tried to help fund the fighter’s journey to Athens, but, in the end, the greater infrastructure was lacking to make it feasible.

Instead, Greenberg, with the Star of David on his shorts, decided to turn pro in 2001. “I am a Jewish fighter who represents all Jews,” he announced. “It is important for people to see there are Jewish boxers. If I succeed, all Jews succeed.”

In six years, Greenberg won 27 consecutive pro fights. He was heavily showcased on the BBC, he boxed in Monte Carlo, Hollywood, Las Vegas and New York, and he regularly sparred the likes of David Haye and Michael Sprott, often holding his own. Yet there were suspicions even back then, even with momentum in full flow, that the hype outweighed the substance.

“Roman Greenberg is a neat, tidy boxer, but I’ve been hearing rumours Mike Holden has put him down in sparring, and it doesn’t look good,” Mark Potter, a former British heavyweight title contender, told me in 2004. “He’s been kept away on dinner shows and stuff, and it’s hard to keep an eye on him.”

Similar testimonies were available elsewhere, as will always be the case whenever a young fighter is powered by hype, but there were no such concerns among the inner circle. At least none made public.

“The first time he boxed in New York we went to a press conference and all the seats had a bit of paper on them,” said Jim Evans, Greenberg’s coach. “On the paper it said, ‘Roman Greenberg is expected to be the first billionaire boxer.’ I had a row with Robert Waterman. I said, ‘Who put that on the bloody chairs?’ He said, ‘Well, because he’s a Jew, some people think he is so marketable he could be the first billionaire in boxing.’ I said, ‘Robert, what are we doing putting all this pressure on this young kid?’”

“I don’t think that bothered him,” is Waterman’s take on the weight of expectation. “I think what bothered him were personal issues. I think he was incredibly homesick to a level we didn’t appreciate. He came from a very difficult family background and there were always issues that needed his attention and were tough to deal with from afar.

“I don’t think the pressure was a problem, but I do think he was made to feel a bit of star. Being young and inexperienced, he didn’t live the life as a result of that. Though incredibly nervous, he believed his natural ability and skill would see him through. If he didn’t train hard enough, he’d be saved on the day.”

Ten years ago, in what would prove to be his final fight, Greenberg, stunned in round two, was saved not by his own talent but by Bill Clancy, a referee. The only person who’d seen it coming was Cedric Boswell, the one responsible for it.

“I’d never heard of him,” said Boswell, now 49. “When I saw the people he’d fought, I realised he hadn’t fought anybody. Also, where I’m from, I’d seen his style a million times before. My own style is similar to that. I knew he couldn’t show me something I’d never seen before. There was nothing to worry about. He didn’t have any power and I knew I was faster than him. If you’re fighting a heavyweight with no power, what’s there to be afraid of?”

In effect, Boswell skim-read the fawning press releases and promptly discarded them. He then heard people speak glowingly on Greenberg’s behalf and deemed it not an indication of a support network but, rather, a sign of weakness.

“We did a little press conference before the fight and then went to a radio station and were sitting next to each other and talking,” Boswell continued. “He talked a little, but his manager was talking about how he was going to beat me and all this stuff. So, I told him, ‘You’re not going to be able to fight for him. Roman’s got to get in the ring and do it himself.’

“I looked at Roman and said, ‘Listen, brother, I’ve seen a whole lot of things you’ve done, and you haven’t shown me nothing. When we get in that ring, I’m going to beat your ass.’ I saw his eyes drop and knew right then I had him. He didn’t believe in himself.”

With the benefit of hindsight, and a knockout win, Boswell now questions the pace at which Greenberg was moved, condemning a record littered with too many “tomato cans” and too many distance fights. He wonders whether Greenberg ever had to dig deep and show his mettle.

“I saw in the first round he wasn’t really there to impose his will,” remembered Boswell, who “thanked God” every night for landing the fight. “I was trying to pick up the pace and he was boxing with a sparring partner’s mentality. He wanted to hold on and then break and be friends. I knew he wasn’t ready, mentally, for a fight.

“I think he had potential, though. I think he had a lot of potential to do well in the heavyweight division if they had moved him correctly. But they didn’t move him right.”

That’s the surface-level reading of Roman Greenberg’s demise. It’s one that deals in records and facts and footage of him being overwhelmed against the ropes, and it’s one with which we are familiar. Delve a little deeper, however, go beneath the hype and its subsequent implosion, get to know the human being behind the persona, and you might discover the root of the problem.

In the case of Greenberg, the human being had human problems, chief of which was his mother’s cancer diagnosis in the weeks preceding his bout against Boswell. Described as being in a “terrible state”, and constantly crying in the gym, Greenberg was sent home by Evans, told to get his head straight, and return to Maidenhead in five days. Evans said if he didn’t see him in five days, the fight was off.

Greenberg returned in the allotted time. Better for the break, better for having seen his mother, he was then informed by his coach he’d be picked up at seven-thirty the next morning for his first run back. “I went around his flat and he walked out looking like Quasimodo,” recalled Evans, who learned Greenberg had somehow twisted his back and sent him for a 10-day course of physiotherapy.

“This was a predominant feature of the problem,” Waterman confirmed. “He’d be in fairly decent shape when he left but come back out of shape. We’d then be playing catch-up in training and he would generally get a niggling injury because of this.

“In retrospect, none of us should have let him go through with that fight. It was he who wanted it. Possibly I wasn’t the best promoter or manager at the time. I take some responsibility for it.”

“I cancelled the fight in America and they were going mad at me,” Evans said. “They were telling me to keep it on. But I knew he was in a terrible state. I said, ‘Look, Roman, everybody can see you’re injured. I don’t want you to fight.’ He said, ‘No, I want the fight. I want the money for my mum.’”

Realising the importance of the payday, Evans issued Greenberg an ultimatum. He told him to come back the following day, do eight rounds of sparring with Michael Sprott, the other heavyweight in the Evans gym, and win every round. “To be perfectly honest, he didn’t win the eight rounds,” said Evans. “He certainly lost the first three.”

Even so, the coach had asked Sprott to “put him under the cosh”, trade vernacular for knock him out, and the ease with which Greenberg coped with the pressure, and navigated the eight rounds, convinced everyone watching he deserved a chance. The next day, Greenberg coasted through 12 rounds and lost not one.

The eventual fight, though, was another matter. Looking back, Waterman concedes it was the wrong “crossroads fight” to take and classifies Boswell as a “contender in the Who Needs Him Club”. But he also rightly points out that many heavyweights have experienced losses like the one Greenberg suffered against ‘The Boz’ and gone on to great success. “Wladimir Klitschko springs to mind,” he said.

At first, it was just a defeat. A surprising one, no doubt, but a defeat all the same. It was the 26-year-old’s Ross Purrity moment, to stick with the Klitschko theme, and only its blowback, its gravity, could be understood, perhaps even forecast, by those acquainted with the human being.

“Jim said to me, ‘He’s never going to box again,’” recalled Waterman. “I said, ‘Give him six to eight weeks and he’ll be going mad wanting to.

“But I totally misread it. I actually think we all misread Roman, Jim included. We all thought Roman was incredibly cool and calm and, if anything, too laid-back. But I think it’s a bit like the ducks swimming across the lake. Everything is serene and calm above the water but beneath the water those feet are going like crazy.

“I think Roman was like that. He was incredibly nervous. His social background, what he’d been through, and being the Russian man, meant you had to be strong and not bothered visibly. But I would say, as a result of that loss, he had a bit of a breakdown.”

Roman Greenberg
John Gichigi/Getty Images

A distraught Greenberg returned to England the day after the Boswell fight and then left for Israel on the Tuesday. Jim Evans, the man from whom he rented a flat, the coach he considered part of his team and therefore part of his extended family, would never hear from him again.

“I couldn’t tell you where he is or what he’s doing,” said Evans, whose late wife, Georgina, was “absolutely heartbroken” when it became clear Greenberg, the young boxer she loved like a son, wasn’t likely to return. “Over 10 years now and I haven’t heard a word from him. That was the end of Roman Greenberg. He just vanished off the face of the Earth. It’s absolutely crazy.”

Evans admits he’s partly to blame for the communication breakdown. Old-school in his approach, he has long held the belief that a fighter should contact the coach if they want to maintain a relationship and argues it’s not the job of the coach to pester the fighter, active or otherwise.

“The trouble is, I never chase anybody,” Evans said, almost apologetically. “You could be the best boxer in the world living next door to me and I wouldn’t go after you. You have to come and see me.

“My boxers, I don’t even ring them. If they don’t turn up to the gym, that’s their problem. I tell my other trainers, ‘Don’t you ring those blinking boxers up. If they can’t ring you and tell you they’re going to the gym, don’t worry about them. They’re grown men.’”

“Jim doesn’t know how to reach him,” said Robert Waterman. “I have – a few times. I’ve even visited him a few times.”

Two years ago, Waterman and Greenberg convened in Haifa and over dinner the former fighter revealed boxing professionally, the whole process, had been one of the biggest mistakes of his life. He told Waterman his major regret was that he never took it seriously, and then, to his old promoter’s surprise, hit him with the kicker. “He said I made his life too easy,” Waterman explained. “That was something I had to think about.”

Dennis Hobson, Waterman’s co-promoter at Fight Academy, had often wanted to warn the team behind Greenberg – the men once scribbled down in my notepad – about the perils of pampering but never felt he had the license to do so.

“I saw the potential,” he said, “but the difference was they were in love with him. They were blinded by love, especially Robert. He was in love with him because he’s Jewish himself. He thought he had the golden goose on his hands.

“But it didn’t really do Roman any good because he was there wiping his backside at every whim. Sometimes you have to say to them, ‘Hold on, you’re taking the p**s now. You have to go and do that for yourself.’ You’ve got to take them out of their comfort zone, so they’re not fazed when the going gets tough.

“It’s like having a beautiful girlfriend and not being able to see past the good looks. I thought he had absolutely everything – marketability and ability – but when he stepped up, when he got hit on the chin or isn’t having a good day, could he hang in there? Ultimately, that’s what found him out. I don’t think he had the tenacity and the desperate hunger to achieve.”

Having had a decade to reflect, Waterman doesn’t dispute this.

“People used to say I was too nice,” he said. “Everyone was looking after Roman like he was a member of their family. If he needed to get somewhere, he had a car. If he needed to go somewhere, he had a ticket. If he needed to stay somewhere, he had a bedroom. He never had any issues. He never lived the life.”

Waterman estimates he has met Greenberg on “probably five or six” occasions since Boswell spoiled the fairy tale, and says that Greenberg, racked with guilt, once told him he had been meaning to call Jim Evans, but that the passing of time made it increasingly difficult. He said he only had himself to blame, yearned to turn back the clock, and had even explored the possibility of a comeback. Waterman, in response, assured him it wasn’t too late.

“The problem was he now had commitments with family and couldn’t fund the process,” he said. “My colleagues and I were happy to help, but we weren’t happy to fund the whole process. He wanted to have enough of a salary to be able to look after his family, which we all agreed on. I took my hat off to him for that. It showed he was taking care of his responsibilities. The sums just didn’t add up in the end.”

In the intervening years, Greenberg, a 36-year-old father of three, has worked security of the anti-terrorism variety – “I don’t mean dealing with drunken brawls,” Waterman clarified – and has now given up any hope of returning, much to Waterman’s relief.

“My gut told me if we had got it restarted we’d have found out he wasn’t a changed man in respect to his discipline,” he said.

“On one occasion in Israel he picked me up from the airport and took me to a hotel. I said I’d be leaving in a few days’ time and he said, ‘Let me take you to the airport.’ I told him it was going to be early in the morning and that it was no problem. I knew he wasn’t great in the morning. But he said, ‘No, I insist.’

“Anyway, he never showed up and wasn’t available on the phone. A few days later, he reappeared on the phone apologising.”

Jim Evans, despite 10 years of silence, holds no ill feeling. “Such a nice bloke,” is how he describes the absent fighter, before saying he possessed the best “heavyweight boxing brain” he’d ever known. Waterman, meanwhile, reckons the man who speaks fluent Russian, Hebrew and English, with a cockney accent, as well as German and Spanish, might have been “too smart” for boxing.

“I know this will sound a bit pathetic, but I think I grieved,” Waterman admitted. “I didn’t grieve the loss of a boxing career, I grieved the loss of relative. To me, Roman was like a member of my family. Everyone loved him. He came to my family for Passover and my parents’ house for Friday night dinner, which is quite a big thing among Jewish people. In fact, his first car was given to him by my father.

“From my family’s perspective, nobody has a bad word to say about him. It was upset, not anger. Commercially, people may have felt let down by him, but, in retrospect, he had to make the decisions. As long as he made them for the right reasons – health and happiness – I don’t really have a problem with what’s happened.”

Certainly, commercially speaking, Greenberg lost out. Though never destined to become boxing’s first billionaire, there was once a three million dollar offer to fight Mike Tyson, just before Tyson was shocked by Danny Williams in 2004, as well as a three hundred and fifty thousand dollar offer to face Vitali Klitschko in 2007. “You can take this as gospel,” said Evans, “because I’m telling you.”

More recently, five or six years ago, a Greenberg link from the good old days contacted Evans with a different kind of proposition. The voice on the phone belonged to Israeli David Porat, the heavyweight’s one-time technical coach, who said: “I’ve got a couple of twin brothers in Haifa and I want you to sign them.” Evans could only laugh. “Not for me, mate,” he replied. “I’ve had enough of these foreign boxers.”