Hollywood Watch Collectors, Watch Out! The Bling Ring Is Coming for You

"I get depressed just talking about it," says 'Shark Tank's' Kevin O'Leary — a three-time burglary victim — of the rise in luxury theft, a common hazard for timepiece lovers (including Ben Silverman and Regina King).

There's one big risk to collecting luxury watches: They all too easily can be swiped.

"I haven't met too many collectors who have not had a watch stolen," says investor and Shark Tank personality Kevin O'Leary, who has lost to theft a grand total of 28 timepieces over the years.

A number of collectors — all interviewed by The Hollywood Reporter in the past few years in its coverage of watches — relate similar tales. After a slew of Ben Silverman's timepieces (including an Omega once owned by his grandfather) were stolen from his apartment a few years back while he was out of town, the Propagate Content chairman tamped down his collecting. Food Network chef Tyler Florence lost a Franck Muller — one he wore on the day he was married — after it was pinched from a repair shop. Emmy-winning actress Regina King still is wistful about the vintage Rolex (a wrap gift to herself) that was swiped, along with six other watches, during an open house at her L.A. home in 2000. "They were all insured," she says, "but there is just a feeling of violation, and you can't insure against that feeling." Other crime victims include Golden State Warriors basketball player Andre Iguodala (who once had a Panerai swiped from the locker room) and KISS drummer Eric Singer, a collector of over 200 watches. Someone nabbed Singer's Swiss Glycine watch, a childhood Christmas gift, during a concert.

As the popularity of luxury watches has spiked, so have thefts. In 2013, a sledgehammer-wielding, burka-clad gang of men made off with more than $2.1 million in watches from Selfridges in London. In December, three Rolexes were pilfered from Gwyneth Paltrow's Goop pop-up in Manhattan. That month, the New York Post splashed across its pages the story of how two prostitutes reportedly relieved Beverly Hills watch dealer Steven Rostovsky of his $590,000 Greubel Forsey Double Tourbillon following a night at a New York strip club. In December, the New York Police Department revealed that a number of women had been targeting men in nightclubs, going home with them and cleaning them out of their watches, in some cases after drugging them. The victims included New York Knicks player Derrick Williams, whose Rolex was swiped. (The report did not allege that Williams was drugged.)

O'Leary vividly recalls three separate hits. In 1999, a burglar broke into his home office and made off with nine pieces sitting in their winders. "None of them were covered by insurance," he notes. He mourns the loss of one in particular, a two-tone Cartier Panthere that he wore to sign his deal to sell The Learning Co. to Mattel for $4.2 billion. For two years, he has had dealers scouring the planet for it. A second burglary in 2005 cleaned him out of everything but the Jaeger-LeCoultre Reverso that was on his wrist. In 2007, O'Leary's original Omega Speedmaster Professional Moonwatch was stolen in Switzerland en route from Omega's Geneva store to its service center for a cleaning. After he demanded a replacement, the parties entered a "long negotiation," he says. "I had to sign an NDA, so I can't tell you the outcome."

While the thefts haven't curbed O'Leary's enthusiasm — he's rebuilt his collection "in some cases with better movements," he says — they have changed his behavior. He now keeps his watches spread among various houses under lock and key. He won't discuss what's in his collection, and he splits insurance coverage between two carriers. "I don't want one place to have a complete inventory." On TV, he wears only his Panerai Luminor Base Acciaio, which is easily replaceable. Still, he says, "Watches are not just about money. They mark time and events." Looking back at his losses, he adds, "I get depressed just talking about it."

Unfortunately, high-end timepieces make particularly attractive targets. There's a strong resale market for watches, especially rare vintage pieces. Sometimes stolen pieces change hands under the table, other times they work their way to unwitting private dealers or auction houses.

"If you think about how art is considered to be very susceptible to theft because it is portable, think about watches, says Jordan Arnold, a former Manhattan assistant district attorney who is now head of private client services for investigative consulting firm K2 Intelligence. "They are smaller than the average work of art and easier to steal if there's the right access." Arnold recalls prosecuting "a well-dressed burglar who stole hotel guests' watches by walking up and down halls and pushing on doors to see which weren't locked shut."

Beyond getting good insurance, most experts recommend maintaining an inventory that's stored separately from your watches, one that includes photographs, serial numbers and all purchase and servicing paperwork. Store timepieces in a bank vault, or, if that's too inconvenient, invest in a dedicated watch safe (top makers include Buben & Zorweg and Dottling).

In the event of theft, first get a police report, then notify the watchmaker and major auction houses — some brands and independent registries maintain stolen databases. Patek Philippe has recovered stolen pieces that were brought into its workshop for repair. Because clients had provided the company with police reports, says Larry Pettinelli, president of Patek Philippe USA, it was able to "return the pieces to their rightful owners."

While some say social media increases the risk of theft by broadcasting in real time what you are wearing and your location, other see it as a valuable potential recovery tool. While New York dealer Andrew Shear normally stays under-the-radar, he posted the story of a rare, vintage stainless steel Patek Philippe, with Breguet numerals and two-tone dial, valued at $350,000 that was stolen en route to its client, on the web two years ago. "I first put it on Instagram," he says. "The whole watch world knew about the situation and became aware it was stolen. Then Hodinkee picked it up and it just raised awareness." The point he says, should it "appear in a pawn shop or at an auction house, people will know this watch was stolen."

Still, recovery is the exception. According to Arnold, less than 5 percent of stolen jewelry and watches are found. Only a few of Orlando Bloom's vintage watches were returned after the LAPD nabbed the so-called Bling Ring gang of teens who robbed celebrity homes, including Bloom's, in 2008 and 2009. In 2012 police returned tennis superstar Rafael Nadal's $380,000 Richard Mille RM027 tourbillon watch, stolen from the five-star Paris hotel where he was staying during the French Open, after tracking an access badge to a hotel barman. But Nadal's custom $525,000 Richard Mille, taken from a Toronto locker during a match four years earlier is still missing.

British actor Gregg Sulkin, star of MTV's Faking It, who owns a Cartier Santos 100, a Rolex Milgaus and a white-gold Daytona, keeps a wary eye. His father, grandmother, uncle and brother have had watches stolen — some straight off their wrists. "I don't wear my watches in nightclubs in London. I don't keep them at home, and I have insurance," he says. "But there's only so much you can do if someone's determined to steal."

A version of this story first appeared in the May 6 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.