UP to his neck in debt, without a TV deal, beaten twice in six months, and with a lawsuit for accidental GBH against him pending – suddenly, at 29, the former world middleweight and super-middleweight champion Chris Eubank found himself all at sea. Retirement was hastily announced then revoked, with sympathy from his contemporaries and the broader public in desperately short supply.

Soon, promoter Frank Warren would hit him with a writ for £84,000 in unpaid VAT stemming from the second Steve Collins fight. American Express would issue an overlapping claim for substantial unresolved credit debt. For years, and a share in his millions, the IRS had been circling. Eubank’s haughty demeanour and apparent contempt for competition had long since alienated him from fellow fighters and the public at large. The returns on his eight-fight deal with BSkyB were so low that former Sun Editor Kelvin MacKenzie was made to resign from his position as Managing Director. With the Lord of the Manor of Brighton defeated and adrift, now was the time for tabloid-fuelled schadenfreude.

Seeing the ruinous state of his finances exposed in public was, for Eubank, a bruising experience. “I wasn’t born with parents who were accountants,” he told The Guardian in 1994 when asked about his rumoured debts; “I come from the streets.” Born in Dulwich, London, in 1966, Eubank’s teenage years were plundered between Hackney and Peckham, largely at one speed – tailspinning in extremis. Only when he left London for more outlandishly violent territory in the South Bronx, New York, was Eubank able to stop his life from spinning further out of control.

Later he would masquerade as a sort of self-made Tory-radical, but neither the faux-Tudor mansion in Hove nor the 10-wheel Peterbilt truck from Fort Lauderdale could stop the past from clinging to him like a bad dream or ghost. The jodhpurs and tweed would obscure without transcending the grim backstory which his adult idyll was meant to suppress. Throughout the mid-90s, Eubank was footing the bill for an unemployed older brother, who persisted nonetheless in selling stories of their bust-ups to the tabloids. In the same decade, his estranged father was discovered sleeping rough in Hastings. Eubank would pay for his return to Jamaica.

More bruising still were the losses to Collins, a fighter whose meagre repute belied an impressive pedigree that was gained in the 1980s through a decade’s hard graft alongside Marvin Hagler in the Petronelli gym. Eubank would assign the first loss to the shadowy interventions of Collins’s personal quack, Tony Quinn, whose mere presence in the days before the fight was enough to reduce him to a jabbering wreck.

The second was harder to attribute to the whims and vicissitudes of pseudopsychoanalysis, however, after Collins ground down the former champion over 12 gruelling rounds at Pairc Ui Chaoimh in Cork. In truth, Eubank had been ripe for the taking for years. Time after time since the first fight with Nigel Benn he had been bailed out either by questionable decisioneering or by his own ability to turn a fight suddenly in the moment. For some time now, Eubank had been a fighter of nagging lulls and indecisive scraps and the odd occasional transcendent moment. Against Collins, there were no more epiphanies left for him to conjure.

Financially imperilled if not quite physically frazzled, Eubank would cancel his overhasty retirement in the name of fulfilling unsatisfied ambitions. The same fighter who had infamously called boxing “a mug’s game” now launched his second coming under the guise of securing lasting affection from a formerly hostile audience. What followed instead was one of the strangest ventures to the Middle East since Charles Doughty spent two years wandering around “Arabia Deserta” calling himself Khalid in the mid-1870s, when Eubank launched himself as a travelling attraction in consecutive fights in Egypt in October 1996 and Dubai the following year.

Whereas Doughty’s travels would take him to “the mawkish mummy-house cliffs, the sordid kella, and perilous Moghrareba of Medain Salih,” as he remembered in Travels in Arabia Deserta, Eubank’s bizarre trip to the desert would see him scrapping with meagre journeymen before grim-faced soldiers in fatigues and a few impassive sheikhs, first in Cairo and then at a Dubai tennis club.

As if to add to the surrealist atmosphere before his first fight in Egypt, Eubank’s entrance married the familiar strains of Simply the Best with an entourage adorned in faux-Egyptian headdress – mingling Tina Turner with Tutankhamun. To compound the anachronism, Eubank’s opponent, Luis Dionisio Barrera, was a 5ft 7in career welterweight whose last four bouts had been lost on the spin. Wearing a cheap yellow cap, with a matte of unkempt hair sponged across his chest, the chubby Barrera bowed apologetically to the four corners of the ring when his name was announced. “Style on the Nile” – despite the name of Eubank’s promotion – this was not. Eubank would stop Barrera when a half-hearted flurry of body shots dropped the portly Argentine to his knees in the fifth.

Odder still than the fight itself was the fact that Eubank stood to lose money from his scanty scrap with Barrera. A failure to drum up interest in Cairo had meant that television coverage was given free to the state-run local channel. Back home, Eurosport carried the fight in the UK as a delayed screening at the cost of £20,000 – small change in comparison with Eubank’s former deal with Sky. “The money is irrelevant,” Eubank would insist to The Guardian afterward. “I felt the crowd was very warm to me. They appreciated the difference between the performer and the human being, which is something that the British public, ill-informed by the media, had trouble with.” Later he would announce his intention to fight in Kuwait, Dubai, Saudi Arabia and Euro Disney.

In the event, Eubank would make his way to only one of those venues when he took his waning roadshow down to a tennis club in Dubai for a scrap with the unknown Camilo Alarcon in March 1997. Once more Eubank’s difficulties in selling tickets and securing payment from Sheik Hamdan and Merser Al Fayegh, the Sheik’s appointment as promoter, would leave him to cover a sprawling tab that would never be repaid. Even worse, he would fall out badly with trainer Ronnie Davies while presiding over the sham in Dubai. Alarcon, who had not fought for 12 months, was less capable even than Barrera. Before a silent crowd accustomed to ballboys and tramlines, Eubank sank the Colombian in four. By the time former antagonist Frank Warren came calling later in 1997, he was ready to return home.

No sooner did Eubank announce his new deal with Warren than he found himself back in the ring in October 1997, on 11 days’ notice, against the unbeaten Joe Calzaghe. Eubank had been preparing for a light-heavyweight bout with Mark Prince when Steve Collins abruptly withdrew from his fight with Calzaghe and retired from boxing. Almost immediately he went from sham in the desert to a main event in Sheffield, in a fight whose higher stakes paradoxically were exactly what Eubank needed once more to crank up the Tina Turner and prove himself again. Used to boiling off weight in the lead-in to his fights, Eubank looked characteristically spry back at super-middleweight – despite not having made the 168lb limit since September 1995 and in spite of a number of knee problems that had majorly hampered his preparation.

Once again Eubank found himself fighting for the WBO super-middleweight belt he had spent his career trying to legitimise. This time, however, he would play an unfamiliar role as a nostalgic crowd favourite against the up-and-coming Calzaghe, whose relentless whirling style and swarming feet made him a daunting challenge for the slowing Eubank. Calzaghe, from Newbridge, Wales, was then as shiny and new as Britpop or Blair – a dashing emissary for a time yet to come. When Eubank was razed to the canvas by a left cross in the first 15 seconds, caught rearing back from a mid-range clinch with his head hanging out in aristocratic fashion, those who predicted a sacrifice were nodding sagely along. By the end of the first round, a confident Calzaghe was doing his own shuffled imitation of Muhammad Ali.

Yet Eubank’s fighting instinct had only been dimmed, not diminished, by his misspent years in the desert. “As I picked myself up from the canvas and brushed myself down, I thought to myself: ‘You’ve got your work cut out tonight, guy,’” he remembered several years later in his autobiography. That would be borne out by subsequent rounds, as Eubank regrouped only to find Calzaghe relentlessly closing the distance across from him. Eubank had never been the most comfortable fighter up close, but every time he sought to hold Calzaghe at a distance, the Welshman would spring into range and swarm the former champion against the ropes. After several exacting rounds, Eubank was barely surviving Calzaghe’s punishing regime.

Forced into contingency, Eubank fell upon a strategy beset with risk yet which brought back memories of prior success. “My constitution was strong enough to soak up the damage [he] might have done in the longer term,” he remarked in his autobiography, “so once I had regained my poise, I thought to myself: ‘I will knock on your door in the 10th or 11th round but, boy, am I going to have to take some stick in the meantime.’” But when Eubank did come calling – in particular, with a fusillade of straight rights and uppercuts in the 11th and 12th – Calzaghe would remain in possession of himself and the answers. Nearing the end, Eubank found himself knocking too late.

Sitting in his changing room with Richard Branson afterward, face bruised and swollen, knees worn down to the bone, Eubank would announce in private his decision to retire. “I can’t do this anymore,” he remembered saying, “I just can’t.”

The next day he would wake up unable to walk courtesy of the knee problems that had dogged him for years. There were not so many next days left for Chris Eubank as a boxer. But, for perhaps the first time in his career, waking up as a loser, he had found what he had always wanted, what he had wanted even more than victory – appreciation. In future, there would be a new answer to questions about retirement: “Life is a show and the show must go on.”

Next up, cruiserweight and Carl Thompson.