You can tell a lot about someone by their watch. Some people wear them for utility—something to check the time without looking at their phone. Others? Well, for them, a watch is a status symbol. A flex. A way of telling the world, "I’ve made it."
And then there are those whose wealth and power come from… let’s call it "alternative revenue streams." Criminals—big-time gangsters, fraudsters, and kingpins—have been known to flash some serious timepieces. And when you’re rolling in illicit cash, why not strap a few thousand dollars (or more) to your wrist?
So let’s dive into the intersection of crime and horology—the watches that have graced the wrists of some of history’s most notorious figures.
1. Pablo Escobar—Rolex Day-Date
Ah, Pablo Escobar. The Colombian kingpin who turned cocaine into an empire. By the mid-’80s, he was making so much money that rats were literally eating millions in cash before it could be laundered. So, what do you wear when your cartel is pulling in $420 million a week?
Enter the Rolex Day-Date—a.k.a. the "President." Gold. Bold. The ultimate power watch. It was the perfect choice for a man who basically ran Colombia for a time. And considering Escobar once burned $2 million just to keep his daughter warm, dropping some cash on a Rolex was nothing.
2. Al Capone—Rolex Prince
Before smartwatches, before quartz movements, and before even James Bond made the wristwatch cool, men carried pocket watches. And one of the most infamous was owned by Al Capone, the Chicago crime boss who turned bootlegging into a multimillion-dollar business during Prohibition.
His watch of choice? The Rolex Prince—a timepiece as bold as the man himself. Known for its unique rectangular shape and dual-dial design, the Prince was a precision instrument for those who wanted both function and flair. Capone didn’t just run Chicago’s underworld; he owned the spotlight. And while his empire eventually collapsed, his Rolex Prince lives on as a symbol of old-school gangster luxury. It’s like Capone himself: sleek, sharp, and utterly unapologetic.That’s old-school gangster luxury.
3. John Gotti—Piaget Ultra-Thin White Gold 9765 Watch
John Gotti loved attention. The suits, the silk ties, the way he strutted out of court after beating another charge. The New York Times called him "The Dapper Don" for a reason.
And if you’re the boss of the Gambino crime family, you don’t wear just any watch. No, you go for the Piaget Ultra-Thin White Gold 9765. Because nothing says untouchable like a black onyx dial and a textured bezel set with a row of approximately 17 round brilliant-cut diamonds on either side.
4. Frank Abagnale—Cartier Tank
You know his story: Catch Me If You Can. Leonardo DiCaprio running through airports. The Pan Am pilot uniform. The phony checks. The FBI is finally catching up. But did you ever notice what Frank Abagnale wore on his wrist?
A Cartier Tank. Sleek. Classy. Understated. The kind of watch that lets you blend in while posing as a doctor, lawyer, or airline pilot. Because if you’re going to con people out of millions, you better look the part.
5. Charles Ponzi—Gold Pocket Watch (Likely Patek or Vacheron Constantin)
Ponzi schemes are everywhere. But the original Ponzi? That was Charles Ponzi in the 1920s. The guy promised investors a 50% return in 45 days—and it worked… until it didn’t.
Like any good scammer, Ponzi lived the high life while the money was rolling in. He wore a gold pocket watch, though records don’t specify the brand. Given his tastes, it was probably a Patek Philippe or a Vacheron Constantin. Because if you’re lying about your fortune, you might as well look like a millionaire.
6. El Chapo (Joaquín Guzmán) – Audemars Piguet Royal Oak
Joaquín "El Chapo" Guzmán wasn’t just a drug lord. He was a Houdini-level escape artist. Prison? No problem. Just dig a tunnel.
When he wasn’t evading authorities, El Chapo indulged in high-end watches, including an Audemars Piguet Royal Oak. Tough, rugged, and ridiculously expensive, it’s the kind of watch that says, "I’m rich, and I don’t care who knows it."
7. Bernie Madoff—1945 Rolex Monoblocco
Ponzi schemes, take two. Bernie Madoff swindled investors out of $65 billion, making him the biggest fraudster in history. And what did he spend his stolen wealth on?
Among other things, a rare 1945 Rolex Monoblocco, a.k.a. The Prisoner’s Watch. The Monoblocco is an 18-carat gold chronograph (ref 3525) known to have been one of 27 watches that the U.S. Marshals Service sold to recover money for Madoff’s victims.
8. Whitey Bulger—Cartier Roadster
For years, Whitey Bulger was on the FBI’s Most Wanted list. A Boston crime boss, murderer, and all-around bad guy, he vanished in 1994 and wasn’t caught until 2011.
What did they find when they finally busted him? A Cartier Roadster. Not exactly what you’d expect from a guy who spent decades hiding out in cheap apartments. But hey, even fugitives need to tell time.
9. Meyer Lansky—Longines
Meyer Lansky wasn’t just another mobster—he was the mafia’s accountant. A financial genius who made millions running illegal casinos and laundering money.
Unlike flashier gangsters, Lansky kept it low-key. His choice of watch? A Longines. Classic. Unassuming. The kind of watch that says, "I’m not here to show off—I’m here to make money."
And he did. A lot of it.
10. Lucky Luciano – Patek Philippe Ref. 1516
Charles "Lucky" Luciano wasn’t just any mobster—he was the architect of modern organized crime. The guy practically invented the Mafia as we know it, complete with a board of directors he called "The Commission." If you’re going to run the underworld like a Fortune 500 company, you better look the part.
And Lucky? He knew style. His watch of choice? The Patek Philippe Ref. 1516 is a masterpiece of Swiss watchmaking. This timepiece, with its clean lines and legendary craftsmanship, was understated yet undeniably powerful—just like Luciano himself. In a world where image was everything, Luciano’s Patek wasn’t just a watch; it was a statement. Precision. Elegance. Authority. The kind of watch you wear when you’re the boss of bosses.
For these criminals, a watch wasn’t just a way to check the time. It was a statement. A message. A way to say, "I’ve made it—and there’s nothing you can do about it." Of course, time eventually caught up with all of them. But for a while, they lived large—with some very expensive reminders on their wrists. So… if you ever see someone wearing a gold Rolex or an Audemars Piguet, you might want to ask how they made their money. Or maybe don’t. Just… keep walking.
*Please note that while the images provide images related to each individual and their associated watches, the exact watch models may vary, and some images may be of similar models or representations.
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