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5 of the Most Daring Heists of All Time

From tyrannical third-world dictators and down-and-out mobsters, to nefarious international business moguls and aspiring socialites born on the wrong side of the tracks, the rogue’s gallery of characters who pull off noteworthy heists are often straight out of Hollywood casting.

But though bank robberies and art heists can net hundreds of millions of dollars, it’s usually elected officials and military strongmen like Ferdinand Marcos that make off with the most cash.  

Speaking of Ferdinand Marcos, he’s first on the list, so let’s get started. 

1. The Rape of the Philippines

Ferdinand Emmanuel Edralin Marcos Sr. was a notorious kleptocrat who served as the Philippines’ tenth President between 1965 and 1986.

And like many dictators in developing countries, he saw the nation’s coffers as his own personal piggy bank, and his take from his time in office made the hauls of the other heists on this list seem like child’s play.  

Championing an ideology he referred to as “constitutional authoritarianism,” Marcos ruled with an iron fist under martial law for nearly a decade between 1972 until 1981, and only grudgingly relinquished control when he was deposed in 1986. 

One of the most corrupt and controversial leaders in a century known for them, Marcos tenure as the country’s strongman was characterized by excess, extravagance, brutality and outright theft of epic proportions. 

Though Marcos’ rise to power was at least partially legitimate, he often made up false claims of his military exploits, most of which turned out to be fabrications. 

Nonetheless, he served in the country’s House of Representatives between 1949 and 1959 and the Senate after that until 1965. 

During his first few years as president the country’s economy grew steadily, and for many the future looked brighter than it had in ages. 

But not surprisingly, the aggressive program aimed at shifting the largely agrarian economy to manufacturing and infrastructure investment was largely fueled by loans from foreign governments and so-called aid organizations, and the debt accrued became unsustainable. 

To silence critics and naysayers, the brash president revised the country’s constitution, harassed independent media outlets and instituted campaigns against everyone from Muslims and alleged communists, to homosexuals and ordinary citizens who dared voice their displeasure at the direction in which the country was headed. 

However, thanks to distractions from the social, political and economic turmoil, Marcos’ grand theft went relatively undetected until the early ‘80s.

In 1983 the country was first rocked by a devastating economic collapse, and then by the assassination of prominent opposition politician Senator Benigno “Ninoy” Aquino Jr., who was a much-loved alternative by common folks who’d had enough. 

Of course Marcos’ and his goon squads were the prime suspects in the murder, and the resulting opposition resurgence shortly thereafter led to a parliamentary election, and ultimately the discovery of documents exposing Marcos’ financial crimes. 

To fend off the attacks Marcos called an impromptu election of 1986, but his bid to remain in power was ultimately unsuccessful and the allegations of mass cheating and shocking human rights abuses led to the People Power Revolution which removed him from power.

To avoid what might have turned into a bloody civil war, Marcos was advised by then US President Ronald Reagan to get out while the getting was good. 

Marcos and his uber-wealthy family fled to the American island paradise of Hawaii and he was succeeded by Aquino’s widow, Corazon “Cory” Aquino.

According to official documents provided by the Presidential Commission on Good Government, the Marcos’ stole between 5 and 10 billion USD from the country’s central bank while in power. 

But though Ferdinand was the mastermind, his infamous wife Imelda played a significant role as well, most notably amassing a collection of thousands of designer shoes that by some estimates cost more than three million dollars. 

In fact, the happy couple hold a title in the Guinness Book of World Record for Greatest Robbery by a Government.

Ferdinand died in Hawaii in 1989, but though the Presidential Commission on Good Government has recovered some of the Marcos’ ill gotten gains, by all accounts his surviving family still lives like royalty, and it’s unlikely they’ll ever be held to account for their crimes. 

2. Dresden Green Vault burglary

Burglary green vault crime scene security by the police

In the early morning of November 25, 2019, brash thieves stole royal jewellery from the Green Vault Museum in Dresden, Germany that was purportedly valued at more than 1 billion USD, though due to their cultural and historic value, their true worth may have been much more. 

Founded nearly three centuries ago, the museum is one of Europe’s oldest, but security was surprisingly lax. 

The items taken included the nearly 50-carat Dresden White Diamond worth approximately 13 million USD, and various other pieces of jewelry that contained more than 1,000 diamonds, rubies, emeralds, and sapphires.

Thankfully, at the time, one of the museum’s most prominent pieces – the 41-carat Dresden Green Diamond – was away on loan at the Metropolitan Museum of Art in New York. 

To create a diversion, the thieves started a fire nearby which caused a brief power outage, though the museum’s CCTV and security systems still functioned. 

At 4 a.m. thieves cut through iron bars around a window to break into the museum’s Jewel Room, where they were recorded smashing glass display cases with an ax and stuffing the loot into sacks.  

Inside for just a few minutes, the thieves eventually exited through the same window and replaced the cut bars to postpone detection. 

But though their actions were recorded, nobody was watching the monitors at the time, and it wouldn’t be until nearly an hour later until the theft was detected 

Following protocol, the unarmed guards didn’t try to find the thieves, but instead called police. 

More than a dozen police units arrived while others set up roadblocks around the crime site, but the museum’s location near the Autobahn likely meant that the bandits were long gone.  

The police initially reported that there were four thieves and that they fled in an Audi A6, which was later discovered on fire in an underground parking lot not far away. 

Police offered a 500 million USD reward for information which could lead to the capture of the perpetrators, but though tips of all descriptions flooded in, their investigation centered on a notorious Arab crime family in Berlin that was suspected of committing other art heists.

The investigation dragged on for years, but in early 2020 scores of police task forces raided more than a dozen homes in Berlin and arrested three suspects, all from a family of Lebanese immigrants. 

Police later revealed that at least seven individuals were involved in the robbery and prosecutors announced that they were investigating four security guards as likely culprits as well, since their response was deemed wholly inadequate – in other words, it was probably an inside job. 

None of the stolen items were ever recovered, but curators and government officials implored the thieves not to destroy them.

But sadly, it’s believed that the thieves did destroy the items to sell them for their gold and gems only, which though less valuable than the pieces themselves, could’ve still fetched between 250 and 500 million USD.  

Later that year an Israeli company reported that the pilfered jewels were being sold on the dark web, but German investigators were unable to substantiate the claim, and the trail eventually went cold.

3. Whitey Bulger & the IRA

Proceeds from one of the largest heists in American history may have ended up in the hands of the Irish Republican Army (IRA), thanks to notorious Boston gangster Whitey Bulger.

For decades Bulger led Boston’s Winter Hill Gang with an iron hand, but as it would be revealed later, he also frequently fed FBI agent and childhood pal John Connolly tips about rival criminals operating on his turf. 

The brazen heist from the Isabella Stewart Gardner Museum was orchestrated just a few days after St. Patrick’s Day in 1990, and the loot taken included 12 works of art, one of which was a Vermeer painting estimated to be worth nearly 200 million USD. 

All told the items were valued at approximately 500 million USD, making it at the time the largest theft of private property in US history, and as is often the case, none of the works have been seen in public since.

On the morning of March 18 at 1:20 a.m., thieves dressed as policemen drove up to the side entrance, parked, and walked up to the museum’s side door.

They rang the buzzer and told the security guard that they were investigating a reported disturbance and were miraculously buzzed in without further questioning. 

Then the guards were rounded up and bound while the intruders waited to see if a silent alarm had been tripped.

Working quickly, they entered the Dutch Room where they took notable paintings like The Storm on the Sea of Galilee and A Lady and Gentleman in Black, shattered the glass and removed the canvases from the frames with razor knives. 

They also removed a large Rembrandt from the wall, but ultimately left it behind, according to investigators because it was just too large to transport.

In the end the burglars got away scott free without firing a shot, but the question remains, if Bulger had orchestrated the heist, why did he give much of the proceeds away?

The answer likely lies in the fact that he’d previously organized a large arms shipment to Ireland, but that the weapons were intercepted by the Irish Navy off the coast of Kerry in 1984, and that Bulger felt he needed to make reparations to his IRA associates. 

With the law enforcement noose closing around his neck, Bulger went on the run in 1995 and spent 16 years on the FBI’s most wanted list. 

Along with his long time girlfriend Catherine Greig, he was apprehended outside a modest apartment complex in Santa Monica, California in June of 2011.

Police found nearly 1 million USD and more than two dozen guns, but no artwork. 

At trial Bulger was sentenced to two consecutive life sentences for nearly a dozen murders, and in 2018 at the age of 89, wheelchair-bound Whitey Bulger was beaten to death in the US Penitentiary in Hazelton, West Virginia, purportedly on orders from the Italian Mafia. 

While some investigators claim that there’s no evidence to support the IRA connection, multiple underworld informants have stated that the paintings are stashed in safehouses in Ireland, though selling them will be no easy task. 

After his death Bulger’s life was the subject of multiple books and two movies, most notably The Departed starring Jack Nicholson and Leonardo DiCarprio, and Black Mass starring Johnny Depp. 

4. Dunbar Armored robbery

Dunbar armored car by Stanislav Kozlovskiy is licensed under CC-BY-SA

The Dunbar Armored car robbery of 1997 holds the distinction of being the largest cash robbery ever in the United States. 

On September 12, six masked gunmen burst into the Dunbar Armored facility in Downtown Los Angeles, California and made off with nearly 20 million USD, or nearly 30 million when inflation is taken into account. 

Orchestrated by Compton native Allen Pace III and carried out with help from five childhood friends, prior to the robbery Pace was actually a safety inspector for Dunbar, making it another classic example of an inside job.  

While an employee, Pace had nearly unrestricted access to many of the depot’s most sensitive areas. 

It was later discovered that he often casually snapped photos in restricted areas without being detected, and that he was able to acquire detailed floor plans which he distributed to his cohorts.  

Ironically, just the day before the heist, Pace was fired for “tampering” with the company’s armored trucks, though there’s no specific word on exactly what he was doing.  

On the night of Friday, September 12, Pace and his partners attended a party to establish alibis, and later though he’d already been fired, Pace was able to get everyone into the building with his old keys. 

By that time he knew the security guard’s schedules and the security camera’s fields of vision, then once inside they waited in the cafeteria and ambushed the guards individually as they arrived for their late night dinner breaks. 

Pace also knew that due to especially high volume on Friday nights, that the main vault was almost always left open. 

After subduing the employees before they could trip the alarms, the crew set about cleaning out the vault, and less than a half hour later they’d loaded nearly 20 million in cash onto a U-Haul truck one of them had rented the day before. 

Successful, the group then returned to the party and hoped for the best. 

Due to his recent firing Pace became a prime suspect, but investigators found no evidence that he’d had anything to do with the heist.  

Meanwhile the gang patiently bided their time, resisting the urge to spend their newfound wealth, but six month after the burglary Pace hired a crooked LA immigration lawyer to help launder the money by purchasing cars, real estate and investments through multiple shell companies. 

Pace also created a few of his own fictitious companies to make his money seem legitimate. 

All seemed to be going well until nearly two years after the robbery, when one of the crew made a classic blunder by handing over a stack of bills for a real estate transaction that were still bound with the original wrapping from Dunbar. 

Shortly thereafter it was discovered that he’d rented a U-Haul truck the day before the heist, and he cracked under questioning giving them all the details and the names of the other men. 

In 2001 Allen Pace was sentenced to more than two decades in prison, most of which he served in the Federal Correctional Institution in Safford, Arizona. 

Other collaborators received sentences up to 17 years, and only about one-third of the money has been recovered. 

Allen Pace was released from prison in October of 2020. 

5. The Scream

The Scream (Norwegian: Skrik)
The Scream (Norwegian: Skrik)

Though artist Edvard Munch named his world-famous painting The Scream of Nature in 1893, it’s now more commonly known as simply The Scream

Featuring a horribly agonized face, it’s become an iconic image that embodies the angst, anxiety and terror often associated with the human condition. 

Inspiration for the painting apparently came when Munch had been out walking and the setting sun turned the sky a particularly vibrant shade of blood red. 

It’s been theorized that the color may have resulted from ash and chemicals pumped into the air by a distant volcanic eruption, or that Munch imagined it due to the stress of his sister being committed to an insane asylum. 

Either way, the artists created multiple versions of his epic work in different media, and some of them have been stolen and recovered multiple times. 

On February 12, 1994, the day the Winter Olympics in Lillehammer got underway, two men broke into the National Gallery, Oslo, and stole its version of The Scream, and they left a note behind thanking the gallery for its “poor security”.

Just a few months later after the museum refused to pay a 1 million USD ranson, Norwegian police recovered the painting during a sting operation, and though they were eventually released on legal technicalities, four men were convicted of the theft, including one who’d been previously convicted of stealing another Munch piece. 

Then in 2004 another version of The Scream and another Munch painting were taken by masked men who raided the Munch Museum in Oslo in broad daylight. 

Museum visitors actually photographed the thieves as they made their way to the getaway car with the priceless works in tow. 

The following year police offered a reward of more than 300,000 USD and arrested the heist’s mastermind and three others suspected of involvement, but no actionable information was divulged, and it was later reported that the paintings had been burned to erase all traces of evidence against. 

After their trial in 2006, three of the suspects were convicted and sentenced to between four and eight years, while the others were ordered to pay hefty fines to the City of Oslo. 

Later that year both paintings were recovered, though police didn’t release details of how they’d tracked them down. 

There was some suspicion that the paintings were fakes, but subsequent analysis proved they were the originals. 

Not surprisingly, shortly thereafter the The Munch Museum was closed for nearly a year, during which time it underwent a much needed “security overhaul.”
When it was auctioned by Sotheby’s in 2012, the pastel-on-board version of The Scream went for an astonishing 120 million USD. 

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