As the sun sets over the Turkish Riviera, its golden rays dance through the windows of Keith Cheeseman’s apartment, perched above the serene Mediterranean Sea. Cheeseman, a figure who seems to have stepped straight out of a gangster film, lounges comfortably with the top buttons of his summer shirt undone. He ponders over his first whisky of the day, with the prospect of a Montecristo cigar lingering in the background. Though he might remind some of Ray Winstone’s character in the film “Sexy Beast,” any likeness is purely incidental.

Now at the age of 83 and having lived through five marriages, Cheeseman carries an air of perpetual amusement. It could be due to a more colorful life than most can claim, or perhaps because he harbors secrets, particularly about his involvement in what was once the world’s largest heist back in 1990—a crime that remains unfamiliar to many.

However, when the conversation turns to unraveling the enigma of who orchestrated the heist, Cheeseman’s demeanor shifts. The smile fades, replaced by a guarded expression. “I have certain ideas,” he admits cautiously, “but it’s a dangerous situation to be in. There can be repercussions.”

His caution is not without reason. The theft, involving hundreds of millions of pounds in a seemingly straightforward street raid in the City of London, was marred by murder, rumors of terrorist links, and a web of betrayals.

Now, decades later, a new documentary led by journalist Marcel Theroux delves into this extraordinary tale. It aims to shed light on this complex crime, revealing that many questions still linger unanswered, even 35 years on.

The extraordinary full story is now being told in a new documentary, fronted by journalist Marcel Theroux, that makes clear there are many unanswered questions, even 35 years later.

On the morning of May 2, 1990, courier John Goddard would not have stood out from the besuited crowds hurrying up and down the narrow lanes of the City. The 58-year-old was carrying a briefcase containing bearer bonds – essentially IOUs used by banks and governments to borrow money that can be cashed in or used as collateral.

Goddard’s briefcase contained 301 such paper bonds, in total worth almost £292million (£726million in today’s money). This was not unusual – at the time, the Financial Times reported, about £30billion worth of bonds were transported by foot around the City every day, the equivalent of close to £75billion today. Former soldiers were often employed as couriers and this system allowed vast sums to be transported on thin sheets of paper. It was just as well: had the £292million been in £50 notes, it would have weighed more than eight tons.

Keith Cheeseman now 83, played a role in what was the world’s biggest ever robbery in 1990, a heist most people will never have heard of

Goddard was employed by Sheppards, a money broker based on Gresham Street, and was on his daily rounds when he entered Nicholas Lane just after 9.30am. Suddenly, a young black man, later identified as Patrick Thomas, held a knife against his throat and ordered him to hand over his briefcase. In just a few seconds, the world’s biggest robbery was over.

Within an hour of the heist, a flash notice was sent to terminals in every bank in Britain circulating the bonds’ ID numbers and warning traders not to accept them if offered. Soon after, the Bank of England, conscious that £292million had effectively just been removed from the British economy, stepped in to support Sheppards by reimbursing it.

This made the robbery a de facto raid on the Bank of England itself, even if the robber had never had to cross the threshold of the building on Threadneedle Street. The central bank knew that there were hundreds of bonds that could be traded in, if the offenders knew how to do it. So the message was relayed to every major newspaper: the bonds would probably be useless and the robbery had therefore been a huge flop.

‘While the theft appeared spectacular,’ reported one newspaper, ‘the thief will find difficulty spending the haul.’ Another cited BoE officials and City of London officers as believing that the robber ‘was purely an opportunist’.

The opposite was true and the bank and police almost certainly knew this. If organised criminals were responsible, they would know of back channels – such as foreign banks with a casual approach to background checks or individuals willing to accept the bonds as collateral – that would have allowed the gang to cash in the bonds. The authorities were now in a race to find who was responsible.

The next time the bonds were seen was in a south London toilet cubicle. In the hours after holding up John Goddard in the City, Patrick Thomas had made his way to Charlie’s, a Lewisham wine bar occupied by day drinkers, gangsters and assorted London rogues.

Thomas – a wiry ‘pavement worker’, or street mugger – slipped in through the back door to avoid detection by the regular police surveillance crews at the front.

High on the success of his robbery, and cocaine, he ushered his friend Jimmy Tippett Jr into a cubicle and pulled a manila folder from a Safeway carrier bag containing the spoils of his morning’s work. ‘It was all different country names, all different company names,’ Tippett says 35 years later. ‘It’s like when you get an A4 pad and you flick through all the pages.’

Cheeseman shakes hands with George Best in 1993. Asked if he knows more about the case than has come out about the heist, Cheeseman pauses, and chuckles: ‘I think so’

Tippett then saw Thomas being summoned to an idling Mercedes outside Charlie’s. Whoever was in the car then delivered the bonds to a Mayfair townhouse, higher up the chain of London’s criminal underworld. There, the hard work of distributing and making money from the bonds would begin.

Thomas was never charged or seemingly even arrested for the robbery, but Tippett and other sources say he was the man hired to carry out the crime.

Within 18 months, he would be dead from a gunshot wound to the head. His death in his stepsister’s flat in Brockley, South London, was officially recorded as suicide, but Tippett, who had been out clubbing with him in the hours before his death, is sceptical. ‘One hundred per cent he wouldn’t take his own life,’ he says. ‘With that robbery and the amount of money involved and the people involved, Pat was silenced.’

If it was a murder, it wasn’t the only one. On July 31, 1990, almost three months after the robbery. Mark Osborne, a disqualified bonds trader and compulsive gambler with a nasal Texan drawl, stepped into McFadden’s, a midtown Manhattan Irish bar, alongside his bodyguard.

He was twitchy – his nerves were betraying him. There waiting for him was Tony Dipino, a slick, confidently dressed Mafia boss ready to get down to business. They sized each other up and talk quickly turned to the ten bonds Osborne was offering for sale, a tiny percentage of those stolen in London. They struck a deal and agreed to do a swap from the back of their cars outside.

There was just one problem: the buyer’s name was not Tony Dipino, it was David Maniquis.

And Maniquis was an undercover FBI special agent, with a special knack for getting criminal gangs to sell him stolen securities.

‘The surveillance agents come in and they place Osborne and his bodyguard under arrest,’ Maniquis tells me all these years later. ‘And I go off into the sunset. I knew that it would be all over the news, so Tony Dipino, for all intents and purposes, retired at the kerb of McFadden’s.’

The Bank of England in the City of London. The robbery was a de facto raid on the Bank of England itself, even if the robber had never had to cross the threshold of the building on Threadneedle Street

Osborne began co-operating and one of his first acts as a government witness was to ensnare his contact in London, Keith Cheeseman, whose conversations – with his estuary English vowels and repeated curses – were secretly recorded by the FBI. Cheeseman unwittingly provided plenty of evidence of his culpability in the laundering of the stolen bonds.

When Osborne told Cheeseman the money for the bonds he had supposedly sold had been handed to him in seven bags that were being kept in his car boot, Cheeseman gave an exasperated laugh and responded like the experienced fraudster he was: ‘Well get the f*** out of there then.’

It’s unclear if the police suspected Cheeseman was involved in the bonds heist before this encounter. But it would be no surprise, for he had form.

In the 1970s, as chairman of the lower league Dunstable Town football club, he persuaded George Best to come out of retirement to play for the club in an attempt to elevate its profile. He funded this – as well as his own high-spending lifestyle – by running a huge fraud out of the club, which saw loans taken out in some of the players’ names. He went to prison for six years, but his descent into crime continued.

He kept exploring new and innovative ways to defraud some of Britain’s biggest banking institutions. An opportunity presented itself in January 1990, when a courier inadvertently dropped £4million worth of bonds belonging to a stockbroker on the streets of the City. They were found by a passer-by, who was rewarded with a magnum of champagne.

The story received widespread publicity and Cheeseman realised an enterprising criminal could take advantage of this antiquated courier system. And indeed they did, months later – although Cheeseman insists he had nothing to do with plotting the Nicholas Street robbery. ‘Something should have happened before, let alone then,’ he tells me today in his rasping voice. ‘It just seemed so simple. You can just snip the briefcase then, woosh, the briefcase is gone. Nobody needs to get bashed on the head.’

While Cheeseman repeats that he was not involved in planning the robbery, he was quickly drafted into the plan to launder the bonds and found himself discussing their disposal at that Mayfair townhouse. A group of men, most of whose identities have never been fully established, opened a bottle of champagne and began counting. Laid out on the table, the bonds looked ‘beautiful’, remembers Cheeseman.

But one thing puzzles him to this day. When they finished counting, he says, the final figure came to £427million – a number he will never forget. Cheeseman is insistent that they got their hands on much more than the £292million cited by Sheppards, the police and the bank immediately after the robbery. ‘There was £135million missing somewhere,’ Cheeseman says. ‘And I never got my whack out of it.’

The extraordinary full story is now being told in a new documentary, fronted by journalist Marcel Theroux (pictured), that makes clear there are many unanswered questions, even 35 years later

He does not know where that £135million went. Perhaps more bonds were being carried in that briefcase than anyone would like to publicly acknowledge, he thinks. But as the only person ever jailed over the robbery, Cheeseman is cheesed off about this apparent heist within a heist.

He had arranged to fence some of the bonds through a contact in Indonesia, but that plan quickly unravelled and instead, they ended up being shopped around to various sources. At this point, the bonds ended up in the hands of people two, three or more steps removed from the robbery and were seized in Cologne, Singapore, Cyprus and elsewhere.

About £77million’s worth was discovered at Heathrow after what authorities insisted was a random search – three Irishmen linked to the package were arrested then released on technicalities. And in Miami, 71 more bonds were found in a package destined for Peru, reportedly a cartel, having been booked on to a flight by a man with an Irish name.

Cheeseman didn’t make it easy for the authorities: after his arrest in London he skipped his sizable bail and fled to Tenerife, where he was arrested again, then extradited to the US. He was sentenced to six years in jail.

A darker fate awaited Mark Osborne, Cheeseman’s Texan contact who had been caught by the FBI. In August 1990, just weeks after his arrest, he was found shot dead in a car outside a Houston shopping mall. CCTV footage captured his partner, with peroxide blonde hair and a CCCP sweatshirt, screaming and crying as police taped off the scene.

Osborne’s killer was never caught, nor were the people who commissioned the Nicholas Street robbery. One who came close to being prosecuted was Raymond Ketteridge, one of the people in the Mayfair townhouse with Cheeseman, and who was later caught red-handed in another FBI recording, then with bonds in his possession in London.

However, just as his trial in London was about to get under way in July 1991, prosecutors dropped the case, mysteriously stating that it was not in the public interest to proceed. Ketteridge, who died in 2009, was never extradited to the US to face FBI charges and it remains unclear why his trial collapsed.

The biggest remaining mystery is who was pulling the strings. Whose idea was it to target the courier? And who stood to gain the most if the bonds had been successfully disposed of? There is one strong theory explored in the documentary, put forward by a British solicitor who worked with Ketteridge and was arrested in relation to the case, but who twice fought off extradition to the US.

‘The IRA was behind it,’ says Jeffrey Kershaw, unequivocally. He says two independent sources confirmed it to him: one a police officer, the other a criminal touting some of the bonds, having earlier tried to enlist him to help sell a painting by the Flemish master, Pieter Bruegel the Elder, that had been stolen by the IRA.

If it was the terror group who commissioned the bonds robbery, the police have never stated this publicly. Officers who worked on the case and who participated in the documentary kept coy about their own suspicions, but an undeniable Irish connection runs through the case.

Either way, Keith Cheeseman is too careful to say what he thinks. Asked if he knows more about the case than has come out, he pauses, and chuckles: ‘I think so.’

Heist: Robbing The Bank Of England is available to stream on crimeandinvestigation.co.uk