4 Of The Most Brilliant Heists Ever

There’s something about an elegant heist that fascinates us. From the germination of an idea, the formation of a plan and the final execution, we are intoxicated by the concept of the “genius” criminal. Glorified in movies like Oceans 11, Oceans 12, Oceans 13 and the blessedly Ocean-free Snatch, we welcome an escape into the world of smooth-talking thieves who are as quick with their wit as they are with their handguns.

Take, for example, the tale of Bruce Reynolds, who in 1963 fastidiously planned the robbery of a Royal Mail train in Buckinghamshire, England. With the help of a mysterious figure known only as “The Ulsterman,” Reynolds and his team of 15 men modified the line signals, brought the train to a halt, and dashed off with over $4.3 million.

Less than four years later, the perpetrators of the “Great Train Robbery” would be immortalized when Peter Yates directed a factually accurate big-screen adaptation of the heist called Robbery. Audiences, of course, have long been lured in by the words “based on a true story,” and Yates’ success with Robbery is at least partially responsible for his subsequent Hollywood career.

We can take Hollywood’s predilection for heist movies as confirmation of our enduring interest. From the escapades of Jesse James to the modern adventures of the Bling Ring — now on DVD, as well — we’ve always found our surroundings a little more thrilling when viewed through the lens of a brilliant criminal.

It is with this fixation in mind that we delve into a corner of our universe populated by these felonious masterminds. Pickpockets, planners and gentleman thieves will all find themselves at home here. From a suicide leap of faith at 10,000 feet to a real-life reenactment of The Ladykillers, we take a look at four of the most brilliant heists ever.


4 D.B. Cooper's Airplane Hijacking

Haul: $200,000

One can hardly begin a discussion of heists without mentioning what is — to many — the quintessential American heist. On November 24, 1971 a man who had purchased a ticket under the name “Dan Cooper” took his seat in the rear cabin of a Northwest Airlines flight. Wearing a dark suit and matching tie, he lit a cigarette, ordered a bourbon and had the general appearance of a background extra from Mad Men.

Then he handed a note to the flight attendant. Initially assuming it was just another raunchy one-liner from a randy businessman, the attendant pocketed the note. Cooper calmly leaned into her and whispered, “Miss, you'd better look at that note. I have a bomb.” With his message relayed, Cooper opened his briefcase to reveal eight red cylinders connected to a central battery.

Cooper ordered another bourbon and laid out his demands: $200,000 in “negotiable American currency” and four parachutes. The FBI scrambled to acquire the ransom money. Cooper released the passengers — the crew remained aboard — and delivered a new flight plan to the plane’s pilot. Remaining calm and gentlemanly throughout the entire ordeal, flight attendants would later testify that Cooper, “seemed rather nice. He was never cruel or nasty. He was thoughtful and calm all the time.”

Twenty minutes later, the cockpit received an alert that the aft airstair had been opened. The plane’s tail section surged upward and the dapper thief parachuted out of the shuddering airliner — unseen by the two fighter planes shadowing close behind — and into the realm of legend.

3 The Antwerp Diamond Heist


Haul: $100 million

Called “the heist of the century,” the theft of diamonds, gold and other jewelry from the Antwerp Diamond Centre was, at the time, the largest diamond heist in history. Nearly three years in the making, the team who executed the theft were meticulous, patient and — above all else — rigorously dedicated.

As a testament to this dedication, two and a half years before the heist, Leonardo Notarbartolo rented an office in the diamond center for $700 per month. For years, he posed as a another faceless diamond merchant in an area inundated with them, building a reputation and credibility. As part of Notarbartolo’s rent agreement, he was provided with a safe deposit box in the vault beneath the center and 24-hour access to the building.

Notarbartolo’s team, calling themselves “The School of Turin,” was an Expendables-style assembly of scoundrels and old-timers: locksmiths, electricians and masterminds. Notarbartolo himself was a lifelong thief and grandfather.

The group’s commitment to groundwork paid off when, in 2003, they made their move. Bypassing a private security force and over eight layers of security including heat detectors, seismic sensors, and Doppler radar, the team snaked its way into what was considered an impregnable vault and absconded with the contents of 123 out of 160 safety deposit boxes.

2 The Banco Central Heist

Haul: $70 million

Credited as the largest bank robbery in history by the Guinness Book of World Records, Paulo Sergio and his team netted a staggering $70 million when they tunneled their way into Banco Central in Fortaleza, Brazil. Sergio, a man regarded as friendly by his neighbors, appeared to live an ordinary life. He owned his own company, Grama Sintetica — Spanish for “Synthetic Grass” — that afforded him the opportunity to pursue his love of gardening.

The only minor caveat was that Grama Sintetica wasn’t real. Instead, the company served as a cover for a months-long subterranean excavation from its storefront to the 1600-square-foot vault of Banco Central. For three months, a team of 10 to 20 men dug a tunnel beneath Dom Manoel Avenue, going so far as to fit it with lighting and air circulating systems. Investigators would later find a trail of dirt, blades, and power-saws in the group’s wake.

To this day, police are still uncertain of how the group made it through the vault’s three-foot thick steel-reinforced concrete floor. The bank itself is unable to figure out why both the cameras and motion detectors inside the vault failed to function. What is known, however, is that the team operated completely beneath the radar for months and worked with an almost mechanical efficiency, employing experts in both math and engineering.

1 The Isabella Gardner Museum Art Heist


Haul: $500 million

In what may be the most daring — and definitely the most costly — art heist in history, two thieves made off with more than $500 million in paintings, including The Concert, one of only thirty-four of Vermeer’s known works. The duo, disguised as Boston police officers, approached the side entrance of the Isabella Gardner Museum at 1:24 a.m., identified themselves as officers, and were buzzed in without incident.

The facade of legitimacy promptly faded when the thieves handcuffed the security guards and asserted, “[t]his is a robbery. Don't give us any problems and you won't get hurt.” Prowling upstairs, the two thieves began to hastily extract the museum’s paintings, even going so far as to barbarically cut Rembrandt’s The Storm on the Sea of Galilee out of its frame.

At 81 minutes, the Isabella Gardner Museum heist is one of the longer engagements on this list. The thieves, loaded up with their ill-gotten gains, made two trips to their car and were gone by 3:00 a.m. It wasn’t until 8:15 a.m. the next morning that police arrived and freed the restrained guards.

Despite a hefty $5 million reward offered by the museum for information leading to the recovery of the stolen art, the case remains unsolved.

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