The “Great Train Robbery” and six of the most notorious heists – but who took the most money?
In the early hours of 8 August 1963, British Royal Mail train driver Jack Mills spotted an unusual red signal light beaming through the dark night in the distance.
It was 3 a.m., and sudden halts were unexpected at this location – so dutifully, he slowed the train to a stop, and crew member David Whitby hopped out to call the signalman using the phone at the side of the tracks.
The only problem? The phone line had been cut.
So David began walking back to the train, when out of the darkness appeared a quickly moving shape that overpowered him in seconds. Before he could warn the driver, a mass of 15 robbers flooded both sides of the engine cabin, ripping Jack away from the controls and clubbing him with a metal bar from behind.
Using insider information from a contact known only as “The Ulsterman”, the gang nicked approximately 120 mailbags from the High Value Packages carriage containing £2,631,784 (then $7,369,784, now £70,428,321.68 or $94,410,221.64), before disappearing into the English countryside.
It wasn’t until 4:20 a.m. that the police received their first distress call from the VHF radio: “A robbery has been committed and you'll never believe it – they've stolen the train!”
Eventually, all of the suspects were nabbed, after police found fingerprints on a Monopoly game the robbers played with (using the money they stole from the train!) while waiting out the search. But loose ends took years to tie up, as some members of the gang fled the country and spent years on the run – and police were only able to recover £343,448 (then $961,757) from the stolen money.
And although the robbers did have to serve jail sentences and face public scrutiny for the rest of their lives, they did walk away with a Guinness World Records title for the greatest robbery from a train.
Yet surprisingly, of all the great heists in the world, the Great Train Robbery (as it came to be known) was not the most lucrative – nor the most mysterious. Whether these criminals stole briefcases or bonds, jewels or famous artworks, or stuck-up banks or businessmen, they all walked away with prizes worth millions or billions of dollars, and inspired legendary police chases that some elude to this very day.
On the anniversary of the Great Train Robbery, we look into some of these curious cases – and what happened to the people that attempted the greatest score of all time.
Greatest robbery of safe deposit boxes
Amidst the extreme civil unrest in 1970s Lebanon, a guerilla force took advantage of the chaos to get away with one of the largest bank robberies in history.
Between 1975 and 1990, the Lebanese Civil War tore up the streets of Beirut as armed religious and militant forces in the region grappled for political power. 1976 was a fraught year, and as the public struggled, banks became prime targets for amassing instant wealth because of the lack of security in the city.
The unguarded money secured by the British Bank of the Middle East in Bab Idriss thus became the prey of an unidentified guerrilla force, who didn’t bother to be discreet about their plans.
On 22 January, the group lit an explosive device from a next-door church to blow a hole in the wall of the bank. They distracted nearby combatants by firing shells, then took advantage of the disarray to blow a second hole into the safe.
From there, a swell of robbers entered the vault, and cleared out safe-deposit boxes with contents full of stocks, gold bars, cash, and jewelry, valued by former Finance Minister Lucien Dahdah at $50 million (£22 million, now £202,365,909.18 or $271,888,717.28) and by another source at an absolute minimum of $20 million (£9 million, now £82,786,053.76 or $111,247,071.18).
The robbers then left the same way they came – through the gaping hole in the side of the wall – and dispersed into the streets, never to be caught or identified. The money was also never recovered.
Greatest robbery of jewels
In 1955, Alfred Hitchcock directed To Catch a Thief in the ornate historical Carlton InterContinental Hotel in Cannes, France – and nearly 60 years later, a single thief stole upwards of $137 million worth of jewels from the same building, in about the same time as a movie trailer.
Around lunchtime on 28 July 2013, a single man slipped through a ground-floor door that was usually locked, disguised in a baseball cap and bandanna. Brandishing a handgun, he threatened three unarmed private security guards and a manager before scooping up a sack containing a briefcase, and a box, and fleeing on foot. The entire robbery lasted one-and-a-half minutes.
The thief had targeted an exhibition of jewels owned by billionaire Lev Leviev which were being shown at the hotel – and prosecutors believed there was more than one person involved giving the thief intel. Somehow he knew that local police were unaware that the exhibition was taking place, and was able to get in-and-out of the building in under two minutes without suspicion.
He successfully walked away into the Riviera with 72 jewels valued at $137 million (then £102,131,445, now £149,577,133.14 or $200,622,525.62) – 34 of which were considered “exceptional”, diamonds twisted into rings and earrings, as well as 38 other lesser jewels.
Though an intense police manhunt followed, diamonds are small, extremely valuable, and difficult to trace – and the thief was never caught.
Greatest robbery of a bank
Similarly to the 1976 Beirut robbery, the largest bank robbery occurred amidst the Iraqi Civil War (2006–2008), during which the resources and reach of the Iraqi police were severely constrained.
On 11 July 2007, when bank employees arrived for their shift at the Dar Es Salaam Investment Bank in Baghdad, Iraq they were shocked to find the front doors open and all the money gone. The guards, who slept at the bank, had also disappeared – leading police to think it was an inside job.
The thieves made off with $282 million (then £210,248,513.16, now £372,791,654.31 or $500,441,108.62) and 220 million Iraqi Dinars (worth around $173,000 at the time), and neither the money nor the robbers were ever recovered. Many think it is likely that the guards were either working for or with one of the sectarian militias active in Baghdad at the time.
However, the biggest unanswered question remains how a relatively small private bank came to have $282 million US Dollars in cash. Investigations immediately suspected a link between the money, Iraqi Government corruption, and poor financial management on the part of the Coalition Provisional Authority (who famously shipped in more than 300 tons of cash during the first few months of the occupation), as well as the sectarian militias that filled the power vacuum in post-invasion Iraq.
As a consequence of these politically-difficult questions, there seems to have been little desire to get to the bottom of this case.
Largest single street robbery
At 9:38 a.m. on 2 May 1990, John Goddard was walking down a narrow alleyway in London when a man suddenly appeared, holding a knife. The mugger demanded John surrender over his briefcase – which he did willingly, because as a matter of policy he didn’t even know the value of what was inside. After snatching away his bag, the robber jogged back down Nicholas Lane, melting back into the morning rush-hour crowds.
But this wasn’t just an ordinary street mugging – John was a messenger, a long-serving employee for Sheppards Money Brokers, who work for affluent banks in the City of London. His job was to physically carry paper bond certificates between various investment firms, banks and brokerages, and that day he was carrying £292 million (then $385 million, now £848,165,539.07 or $1,137,461,912.33) worth of bearer bonds.
At first, police thought this was just an opportunistic robbery – a common thief would not have access to the markets and resources needed to convert the collection of paper certificates into cash, and they would soon expire anyway. The press were told that the bonds all had trackable serial numbers (true) and that this meant it would be impossible to cash or trade them (untrue).
At the time, around £30 billion in bonds passed through London brokerages every day, meaning that even in the City it was by no means certain that these particular bonds would be checked and noticed. If someone traded them in another country, or used them as collateral for a loan, it would be even less likely to be reported to the authorities.
Within a few days, however, detectives began to hear rumours from informants linked to London's criminal gangs. It seemed that this robbery was in fact a carefully organized part of a larger conspiracy. There was nothing that could be used to make arrests, but certain key individuals were put under surveillance. The FBI also joined the hunt, as they believed the robbery was related to an international money laundering operation they were already investigating.
The big break in the case came with an FBI sting called “Operation Soft Dollars”. This involved creating an FBI-run fake Mafia bar on 42nd Street in Manhattan and setting up an agent as “Tony Dipino”, supposedly a high-ranking member of the New York Mafia.
On 31 July 1990, a Texas-based financier called Mark Osborne was arrested while trying to sell $10 million of the stolen bonds to Tony Dipino. Faced with a long jail sentence, Osborne agreed to wear a wire and turn on his former co-conspirators, which led investigators to three other alleged players in the scheme, British nationals Jeffrey Kirshel, Raymond Kitteridge and Keith Cheeseman.
On 16 August 1990, Osborne's FBI handlers lost track of him. He was found dead five days later, executed by two gunshots to the head. With their key informant gone, the investigation faltered. By the end of the year, authorities had recovered £290 million of the bonds (the remaining £2 million had expired unused) but were seemingly no closer to figuring out who had carried out the robbery or who had organized the whole scheme.
The case against Kitteridge collapsed in July 1991 when the prosecution suddenly decided to drop the charges, for reasons that have not been disclosed. Most of the other 25 people arrested in relation to the crime were released without going to trial as a consequence of this first prosecution falling apart. Only Cheeseman and another person involved in money laundering, John Traynor, were ever convicted in court.
Police do believe that the mugging was carried out by Patrick Thomas, a petty crook from south London, but Thomas was found dead from a gunshot wound to the head in December 1991, and was never charged with the robbery.
Greatest art robbery
The empty frame, center, from which thieves cut Rembrandt's "Storm on the Sea of Galilee", remains on display at the Isabella Stewart Gardner Museum in Boston. Image credit: Alamy.
On the night of 18 March 1990, two men dressed as police officers were buzzed into the guardroom of the Isabella Stewart Gardner Museum in Boston, Massachusetts, USA during the night shift. But instead of going to work, they overpowered the other guards and rushed about the museum, carefully cutting paintings out of their frames and grabbing a total of 13 objects before vanishing back into the streets of Boston. The estimated value of these works came to $500 million (then £372,705,000.00, now £1,082,587,456.30 or $1,452,404,744.31)
The artworks stolen were The Concert by Johannes Vermeer; The Storm on the Sea of Galilee, A Lady and Gentleman in Black, and a charcoal self-portrait by Rembrandt Harmenszoon van Rijn; Landscape with Obelisk by Govert Flinck (a student of Rembrandt); Chez Tortoni by Edouard Manet; and five sketches by Edgar Degas. In addition to these works, the thieves also stole a French Imperial Eagle Finial (from a Napoleonic-era military standard) and an ancient Chinese gu or ceremonial cup.
However, the choices made by the robbers have long baffled investigators. The Rembrandt and Vermeer works were obvious choices, being both extremely valuable (the Vermeer painting has been valued at $250 million on its own) and all located in the same room. However, the Landscape with Obelisk was worth relatively little.
Additionally, the Manet painting was fairly valuable, but located on a different floor, far from all the other stolen pieces. The Degas sketches, similarly, were of little value (no more than $100,000 for the whole set) compared to other artworks that the thieves would have had to pass to get to them (which included pieces by Raphael, Botticelli, Michelangelo, and Titian). Most confusing were the gu and finial, neither of which were worth more than a few thousand dollars.
Although several suspects have been suggested by the Boston Police, many have passed away in the years following the heist. Police have considered members of the Boston Mafia, previously convicted art thieves, and a long list of local opportunists as potential suspects, but still no-one has ever come forward with a credible lead. And despite a $10 million reward being offered by the museum, the artworks are missing to this very day.
Greatest robbery of a bank by a statesman
In May 2003, the United States Treasury confirmed that on 18 March of that year, Qusay Saddam Hussein – the second son of former Iraqi President, Saddam Hussein – worked with his accomplice Abid al-Hamid Mahmood to steal $1 billion (then £572 million, now £1,155,737,965.11 or $1,550,441,642.33) from the country’s Central Bank.
Acting on the orders of his father, Qusay and Abid ordered bank employees to load up three tractor-trailers with the cash, which included $900 million’s worth in $100 bills!
The following day, the US-led invasion of Iraq began – and according to a leaked letter, Saddam had ordered $920 million to be withdrawn from the Central Bank and given to his son Qusay. It still is not known where exactly that money went.
To date, this is still the largest bank heist in history – but similarly to the Dar Es Salaam Investment Bank robbery, the history of this category is complicated by the fact that many of the largest thefts have been carried out by heads of state against the banking systems of their own countries.
This action isn't technically illegal as it was carried out by an absolute ruler unfettered by the rule of law, but still of course has dramatic ramifications for the people that depend on that money to survive.
Want to read more about these criminal records? Check out our 2026 edition of Guinness World Records, which features many True Crime record titles!
Header image: Police investigation after the Great Train Robbery. Image credit: Alamy