The 5 Most Audacious Heists of the 20th Century

This week marks the 70th anniversary of the Great Brink’s Robbery, regarded at its time as the “Crime of the Century.” To be fair, that appellation has been afforded to any number of high-profile crimes, but it does lead to the question: what really WAS the Crime of the 20th Century? Putting aside things like political assassinations and other frequently discussed murders to focus on heists and robberies, here are five contenders, either in monetary value or sheer audaciousness, that might be the big score.

1. The Great Brink’s Robbery (January 17, 1950)

A burlap sack full of money that was recovered by the FBI.
Burlap money bags recovered in a Boston junk yard from the Brink’s robbery. (

The biggest robbery in the history of the United States (at the time), the hit on the Brink’s Company building in Boston was the work of an 11-member crew. The gang actually showed remarkable discipline, working together for two years ahead of the event. Their elaborate plan included sneaking into the building to duplicate keys, hours of observation, and even stealing the alarm plans. The group even assembled for the heist six times before they finally decided to pull it off.

On the day of the robbery, seven of the crew went inside, dressed to approximate Brink’s uniforms with the addition of gloves and rubber Halloween masks. They tied up the employees inside and took all the loot they could get their hands on. Upon their escape, they counted the loot, passed out some of the $2.775 million haul (which they agreed not to use for six years, which was the statute of limitations at the time), and went their separate ways with their various stories to cover possible questions about their whereabouts.

Eventually, the group began to splinter. After Joseph O’Keefe was pinched twice for other charges, he held fellow gang member Vincent Costa hostage, demanding that Anthony Pino cough up his share of the loot (Costa being Pino’s brother-in-law). Pino paid, but put out a hit on O’Keefe; O’Keefe survived a gunshot wound and flipped on the rest of the crew. Eight members of the gang eventually served time, but less than $60,000 of the score was ever recovered.

2. The Lufthansa Heist (December 11, 1978)

A Lufthansa jet on the tarmac at Frankfurt Airport
(EQRoy / Shutterstock)

If you’ve seen Goodfellas, this will be very familiar. Deutsche Lufthansa is the largest German airline, and they would carry currency into JFK International Airport in New York. Jimmy Burke (fictionalized as Jimmy Conway in the film) put together a crew to hit one of the currency deliveries. Half-a-dozen men entered the facility while two drivers waited; the break-in crew took employees hostage and loaded up 72 cartons of the untraceable money. It was a haul worth $5 million in cash with an additional $875,000 in jewels.

One of the drivers, Parnell “Stacks” Edwards, had been ordered to take the van he drove to Jersey so that it could be destroyed in an auto yard owned by John Gotti. He didn’t, instead leaving in parked in front of a hydrant by his girlfriend’s place, drawing police attention; members of the crew took out Edwards for not following orders, but by then the police were already gathering prints and evidence from the van. Over time, a number of other crew members and associates were murdered, allegedly on Burke’s orders. No case came together until Vincent Asaro was tried in 2014, but he was acquitted. To this day, the money and jewels have never been found.

3. Dunbar Armored Robbery (September 12, 1997)

If you’re judging by the biggest robberies, this is your winner. At a take of just under $19 million, it’s the largest cash robbery in U.S. history. It was masterminded by Dunbar safety inspector Allen Pace, who used his inside knowledge and observations of the Dunbar Armored facility to plan the job. Assembling a crew of five of his childhood friends, Dunbar led his team through routine that allowed them subdue the employees one by one and access a vault at a time that it was scheduled to be open. They exitedwith the largest bills and the recording devices that they boosted from the security cameras. The group almost got away with it until co-conspirator Eugene Hill paid someone with cash that was wrapped in the company’s straps; the person tipped police, and Hill flipped on the others. Pace got a 24-year sentence, but nearly $14 million remains missing today.

4. Isabella Stewart Gardner Museum Heist (March 18, 1990)

A portion of Johannes Vermeer's painting, The Concert.
The Concert, Johannes Vermeer [Public domain]
You could call this one a masterpiece, or maybe a group of masterpieces. That’s what’s still missing nearly 30 years later in a museum takedown that saw 13 artworks valued at around $500 million walk out the door. While the plan is seemingly simpler in conception than the other heists on the list, it’s notable for the lack of evidence that the thieves left and the fact that nothing has been recovered in nearly 30 years.

Taking advantage of the general St. Patrick’s Day chaos in Boston, two men dressed as police gained entry to the museum after hours, tied up the two guards, and stole a group of art that included a rare Vermeer and works by Rembrandt and Degas.

While the FBI investigated the guards closely, they quickly decided they weren’t involved. Suspicion then fell on the labyrinthine network of criminal gangs that pervade the city. Infamous crime boss Whitey Bulger was investigated; not only did Bulger protest his innocence, he was incensed that the job happened on his turf and had his own people investigate. By 2015, the FBI declared that they had a reasonable idea of who committed the crime, but that both suspects were, by then, deceased. Though other leads and stories have surfaced over time, the art was never found.

5. Miami International Airport Robbery (November 6, 2005)

This one plays like a crossover of other heists. Onelio Diaz, a Brink’s guard at the airport, took note of the lax security surrounding Lufthansa cash transports and told his buddy, Karls Monzon. Diaz didn’t want to rob his own workplace, but Monzon said he’d do it. Monzon planned for months, including renting hotel rooms that overlooked the area for observation and stealing cars out of Jacksonville and hiding them in a semi-trailer for the getaway. When it was time to move, the team hit the open area where the cash was being unloaded; with guns drawn, they grabbed bags loaded with $7.4 million in cash and split. No one was hurt.

Monzon tucked his cut away while he and his wife continued work their day jobs. However, in a twist out of Goodfellas, Monzon’s crewmate (and brother-in-law) Jeffrey Boatwright started spending. A Salon interview with Monzon recounted that “Boatwright’s lawyer said his client spent nearly all of his $1.4 million share on “utter decadence” — jewelry, drugs, alcohol, prostitutes and nights at strip clubs.” Boatwright’s spending attracted so much attention that he was kidnapped and held for ransom twice by other criminals that had their suspicions about Boatwright’s new source of income. Monzon paid for his brother-in-law’s release the first time, but wasn’t planning on doing it again. However, that’s when he got arrested by FBI agents that were onto him and Diaz. Monzon, Boatwright, and the rest of the crew pled guilty; they and the kidnappers are served time, although ironically Monzon’s sentence was reduced by six years for helping the police catch Boatwright’s kidnappers. He also directed the FBI to his personal stash of the loot, over a million dollars; the rest of the remaining money was never recovered.

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