Largest single street robbery

The highest value of goods stolen by a street robber or mugger in a single incident took place in the City of London, UK, on 2 May 1990. At 9.38 a.m., a messenger called John Goddard was robbed of his briefcase by an unknown man who threatened him with a knife. The briefcase contained £292 million (then $385 m) in bearer bonds, including certificates of deposit and Bank of England Treasury bills, which he was transporting for his employer, Sheppards Money Brokers.

To explain how and why John Goddard came to be carrying items with such a high value down a city street, it's necessary to explain something about how money markets worked in the pre-digital age.

A bond is basically a debt made into what's called a negotiable instrument (i.e., something that can be bought and sold). When they're in need of money, governments or organizations issue bonds, which investors can buy, essentially lending the money to the issuer and getting a tradable IOU in return. Most bonds are "registered", meaning that there's a central ledger that records who owns what, and where interest payments and the final balance (paid when the bond expires, or reaches maturity) should be paid.

In the pre-digital age, however, the process of issuing registered bonds could be slow. For short-term debts, needed to service immediate funding requirements, the Bank of England would issue what were called Bearer Bonds or Treasury Bills. These were much simpler things: if you bought one, you were given a paper certificate; if you sold it, you gave the new owner that certificate; whoever was the bearer of the physical certificate could redeem the value of the bond.

The financial institutions of the City of London traditionally used these Bank of England-issued bonds as an easy way to move large sums of money around. The Bank of England, as well as many other institutions, employed "messengers" whose job was to physically carry these bearer bonds between the various investment firms, banks and brokerages. These messengers were traditionally trusted long-serving employees, often with a military background. They wore suits, often with some sort of insignia (such as a lapel pin or a special tie) that showed who they worked for, and carried the bearer bonds in briefcases.

On 2 May 1990, Goddard was doing his usual rounds, dropping off bonds at a handful of building societies and brokerages before heading back to his office on Gresham Street. His route took him down Nicholas Lane, one of the old city's many narrow alleyways, where he was stopped by a man with a knife. Goddard, who as a matter of policy was never told the value of what he was carrying, surrendered the briefcase and the mugger jogged away, quickly blending in with the morning rush-hour crowds.

At first, the City of London Police assumed that this was an opportunistic robbery, and were not hugely concerned – 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 (which was true) and that this meant it would be impossible to cash or trade them (which was not true). 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 planned 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.

Law enforcement's first notable result came on 30 May 1990, when an allegedly routine baggage check at London Heathrow Airport turned up £77 million worth of the stolen bonds. They were in the possession of a known fence (dealer in stolen goods) with connections to Irish organized crime and the IRA. Although the police were able to recover the stolen bonds, the fence wouldn't talk, and had to be released on a legal technicality.

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", purportedly 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 though. Only Cheeseman and another person involved in money laundering, John Traynor, were ever convicted in court.

In the years since, rumours about the "true" size of the haul and the people involved have been published in various true-crime books. Several assert that the knifeman was a low-level drug dealer with connections to organized crime called Patrick Thomas. Thomas was shot dead on his doorstep in south-east London on 29 December 1991, and the gunman has never been identified. Allegedly the original plan was to cash the bonds through a fence in Switzerland, but that person pulled out due to the unexpected size of the haul and the publicity it attracted. This left the group, now out of their depth, having to shop around their stolen goods to various international criminal syndicates.