The criminal lifestyle is glamorous. Or, at least, so it appears on TV and in movies. When we read about real-life criminals like Al Capone or fictitious ones like Vito “The Godfather” Corleone, they’re inevitably portrayed more like movie stars than dangers to society. We love glitz, and nothing shimmers brighter than ill-gotten goods.
When you’ve reached a high enough level of success, no matter how you got there, the spoils of your victory tend to be impressive. This is why popular media usually portrays famous criminals as fashionable, decked out in the finest clothes, hats, and watches. Expensive timepieces, in particular, have a long history in the mythos of criminality.
Today, we’re taking a look at the stunning watches that have adorned some of history’s most notorious criminals – both real and imagined.
Gangster Watches: Crime pays
Despite everything our society, culture, and moral leaders teach us about living honorably by the law, we regularly venerate criminals. Outlaws, lawbreakers, rebels; we can’t get enough of them. Every generation and all cultures have their criminal heroes, the men and women who broke the law of the land and became legends for it.
Partly, this is because we like the idea of rebelling against unjust laws (Al Capone ascended to power during the Prohibition era). More importantly, though, the life of the successful criminal appeals to our desire to be rich, and to do it outside the drudgery of modern life. The image of the criminal mastermind sitting atop his empire is pretty intoxicating.
In reality, for most low-level criminals, crime doesn’t pay. The prisons are full of people who imagined they’d one day be the Kingpin. Even most crime bosses (again, in both the real and imagined world) wind up losing everything. And yet, the myth of the criminal genius still shines bright, like the glint of a Rolex’s pristine crystal face.
Al Capone’s Pocket Watch & Rolex Prince
Though America’s outlaw history stretches back to the nation’s origins and includes dozens of Wild West varmints, the American criminal that best encapsulates our modern idea of the Crime Boss is Al Capone. Making his money as a bootlegger and boss of the Chicago Outfit criminal organization, Capone is the quintessential gangster.
He has been portrayed or fictionalized in countless films and TV shows, and if there is one thing the portrayals usually get right, it’s his sense of fashion. Capone was a dapper man who enjoyed his share of spoils. One of the ways in which he showed off his wealth was through his timepieces.
Capone owned multiple timepieces, as any watch aficionado would, but his two most famous watches were a diamond-studded pocket watch and a gold Rolex Prince. The pocket watch, a triangular timepiece with 72 diamonds set into the bezel, sold at auction in 2017 for $84,375. More diamonds surround the famous gangster’s engraved initials, “AC”, which appeared on the case. At the time of the auction, the watch still included the white gold chain and gold-toned hands.
The pocket watch was made by the Illinois Watch Company, a company that doesn’t quite enjoy the reputation of a Swiss watchmaker, Rolex. Rolex has spent the last century building its reputation as makers of both exquisitely designed watches and rigorously accurate mechanical timepieces. At the same time that Al Capone was building his empire, Rolex was establishing its own renown in the watchmaking world.
It’s thus fitting that Capone would have owned a Rolex wristwatch, even at a time when wristwatches were just starting to come into fashion for men. Capone’s Rolex Prince had a rectangular, gold case with a second-hand subdial.
The Prince watch line was one of Rolex’s first big lines, but it’s long fallen out of favor. As recently as 2015, Rolex released a set of Prince watches under their Cellini line, but they no longer seem to be available through the company (Authentic preowned Cellini watches can be found through online from sites including Bobswatches or see Prince models on eBay.
Al Capone’s eventual downfall, a result of being convicted of tax evasion, did little to undermine the lore around him and the life (and prestige) of the gangster. If Capone’s rise to power has come to represent a uniquely American myth, he is hardly the only criminal around the world to parlay his obsession for power into a glamorous lifestyle.
Pablo Escobar’s Watches: Diamond-encrusted Rolex
Colombian drug lord Pablo Escobar rose to power in the 1970s and became the most famous criminal in the world in the 1980s. He was arguably as famous as Capone and almost certainly more dangerous, creating a narcotics empire that was responsible for much of the world’s cocaine supply. He has been called the “wealthiest criminal in history,” with one of his nicknames being “El Padrino,” or, “The Godfather.”
Like Capone, Escobar has been the focus of countless books, documentaries, and media portrayals (most recently, the Netflix series Narcos). His crimes and rise to power are certainly cinematic, but our collective fascination with the man is probably equally due to his opulent lifestyle. Even when he spent time behind bars, Escobar lived like a king.
Nothing better encapsulates Escobar’s lavish tastes like his Rolex Day-Date watch, an almost comically blinged-out solid gold timepiece covered in hundreds of diamonds.
Unlike Capone’s Prince, the Rolex Day-Date is still in production and represents some of the famous Swiss watchmaker’s most prestigious timepieces.
Escobar’s watch was sold at a Colombian auction in 2013 along with the former goods of numerous drug lords that had been seized by the government. That Escobar’s Rolex only sold for $8,500 when it was valued at nearly nine times that much probably speaks to the terror Escobar continues to instill in Colombia, even though he died in 1993. As the anonymous buyer of the watch explained, “You never know who might track you down and ask for their things back.”
Bernie Madoff’s 46 watches
When we think of major criminals, we generally think of the Capones and Escobars of history, but some of the biggest crimes in the world are committed by the suit-and-tie crowd. Look no further than Bernard “Bernie” Madoff, a former stockbroker and billionaire who is now famous for operating the largest Ponzi Scheme in history.
The failed scheme that eventually brought Madoff down lasted for years and involved $17 billion in fraud (initially believed to be as much as $65 billion). The schadenfreude in witnessing a bunch of Wall Street millionaires be taken in by a giant scam was undercut by the fact that Madoff’s downfall ended up hurting an untold number of “regular” people. His crimes weren’t as flashy or cinematic as Capone or Escobar, but there’s no question he was just as much a criminal.
Following his arrest in 2008 and a sentence of 150 years in prison, many of Madoff’s possessions were auctioned off in New York City. Along with clothing, assorted household items, and other odds and ends, the bulk of the auction was the disgraced broker’s 46 watches. It turns out, like Al Capone and Pablo Escobar, Bernie Madoff had an infinity for high-end watches.
With so many watches, we couldn’t possibly discuss them all, but there are a few highlights. In addition to an assortment of Rolexes, including a rectangular piece from the 1930s that resembles Capone’s Prince, Madoff’s collection included an assortment of Switzerland’s finest: an 18-carat gold Jaeger-LeCoultre Reverso Duo, silver and gold IWC Schaffhausen Portugieser chronograph, and a lady’s Frank Muller Casablanca.
All of those watches retail in the thousands, though there were other watches in the collection that were less extravagant. His collection included a watch from French watchmaker Poiray that sold for around $700, and a whole slew of Swatch watches that could be picked up for less than $100. Those were definitely the exception, though, as most of the collection featured some of Swiss watchmaking’s most prestigious and admired brands.
I don’t know what it is about a life of crime that makes a Swiss watch look so appealing, but there’s clearly a link.
Click here to see the watches worn on wall street, surprisingly Maddof is not the only one who wore Swatch!
Crime and Time
No matter what side of the law you land on, watches have long been a symbol of success and power. The movers and shakers in all industries appreciate the fine craftsmanship that goes into a Swiss watch. Perhaps, then, it should come as no surprise that Rolex is the go-to timepiece of crime bosses.
Then again, maybe that suggests that the line between a criminal enterprise and a “legitimate” business is very fine. Nah.
Click here to see watches worn by Hollywood Criminals, including watches worn in Scarface, The Godfather and Oceans Eleven