Pret-a-Reporter

How a Vintage Rolex Obsession Can Drive You Crazy

Illustration by Lars Leetaru

"Once clients know what they want, they start stalking you," says a watch dealer, as the hunt for classic Rollies becomes a "frenzy."

The vintage collector is a radically different beast than the average timepiece lover, pining over objects that are rare, quite often unobtainable and wildly expensive. And when it comes to Rolex — where modest variations in coloring, fonts and serial numbers can make for huge price differences — collectors can go seriously down the rabbit hole.

"Every collector is crazy in his own way," says watch dealer Alessandro Ciani, whose appointment-only shop in Westlake Village, Calif., is a treasure trove of vintage. He has seen the telltale signs: collectors obsessing for weeks over what to buy while constantly coming in to try on a watch and bringing in friends to get their opinions. "Once they know what they want," says Ciani, "they start stalking you. They will call you at midnight, at 7 a.m., when you're on vacation. A pathology of the real collector is this obsessive mania. They get into a frenzy."

The anxiety levels are high because a great vintage watch is a big investment. And as collecting has gone global thanks to the Internet, perfect pieces have been snatched up, leaving a sea of overpolished cases (patina is in style now) and mismatched Frankenwatches (those dreaded pieces put together from disparate parts, in some cases not all vintage).

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"People want watches in all-original shape, never been polished and with original box and papers. That's what's selling, and they are getting harder to find," says dealer Craig Evan Small of West Hollywood's Craig Evan Small Estate Jewelry.

As a consequence, the demand for something rare and unmolested has caused Rolex prices to more than double in the past few years. At the established watch auctions, a vintage Rolex — which the brand defines as anything 27 years or older — routinely sells for six figures. The most expensive one ever, a 1949 Oyster Perpetual, gaveled last year for $1.2 million.

Other models also command steep prices. A 1955 Rolex 6542 "Red" with a GMT Bakelite bezel can fetch more than $100,000, and an early edition Rolex Sea-Dweller can outpace the cost of a new Mercedes C-Class. The holy grail, a Paul Newman dial Rolex Daytona Reference 6239 — so named for the actor who wore a 6239 as his everyday watch ­— can cost hundreds of thousands of dollars. This for a stainless steel watch that went for $210 new in 1965.

"I sold Orlando Bloom a perfect Paul Newman Daytona about 10 years ago for $50,000 — it was one of the watches that the Bling Ring stole that he got back — it's worth more than $150,000 now," says Small.

The market is so strong that collectors can count on most Rolexes gaining value over time. "If you know what you're buying, you can sell it for a lot more," says Ciani.

People collect vintage Rolexes for a few simple reasons, starting with the cool factor. If vintage Pateks are the equivalent of Rolls-Royces, then vintage Rolexes are old Porsches. Rolex wearers are known for their feats of derring-do: climbing Mount Everest, winning car races and, in the case of James Cameron, diving 11,000 meters to the bottom of the Mariana Trench with a custom Rolex Deepsea Challenger strapped to the robotic arm of the manned submersible.

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"Rolex is a tough watch," says John Edelman, the CEO of Design Within Reach, who has a collection of about 75 timepieces, including a 1972 Rolex Daytona given to him by his father and a 1970s Daytona he bought last year. "It wasn't meant for special occasions. It looks just as good with a tuxedo as with a racing uniform as with an old pair of jeans."

Some fanatics love how much there is to learn. Armed with arcane knowledge, aficionados find camaraderie with other collectors. "With Rolex, it's about the knowledge and the vast education of the community as a whole," says L.A. Clippers star J.J. Redick, whose collection includes a valuable 6263 Paul Newman with a panda dial, which, in collector parlance, means a white face with black subdials.

Admits Alexander Yulish, an L.A.-based artist who recently bought a 1955 Oyster Perpetual for $3,400: "I have three vintage Rolexes. It's crazy how two watches have different colored dials, and one goes for $10,000 and the other for $160,000." He'll visit vintage shops up to three times a week to "see what's new."

Not long ago, Yulish got obsessed with a vintage Rolex that would have set him back $35,000. "That's not, like, nothing," he says. "It's amazing how you can rationalize things. It's like, 'I'm buying it, but it will only appreciate, so technically I'm not buying it for anything — I'm actually going to get paid for wearing it.' " In the end, he decided not to splurge.

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Some collectors like the thrill of finding watches on eBay or at estate sales. "I love the hunt," says Edelman, who bought his Daytona through such a sale after bargaining for weeks with the owner. "She didn't know what it was. I got a good deal on it. I found an original box. I bought the little plastic tags that came with these watches. I like making complete sets." Yulish says he "just really doesn't trust eBay. I'd rather spend a little more money going to a store and know what I'm getting." Others prefer the auction house route. "If there are any problems with the watch, the auction house will take it back," says Small. "That's more than you can expect from a lot of the dealers."

Solid vintage Rolexes, however, don't have to set you back the price of a Malibu summer rental, as you can pick up an infinitely cool 1960s Datejust for less than $3,000. "There's a lot of bang for your buck with Rolex — like a great matte dial 5513 can be had [for] about $8,000 to $10,000," says Redick.

"For me, collecting watches isn't an obsession, and it's not a hobby. It's just one of those things," he continues. "But I jokingly tell people that it's a disease and it spreads. Look at it like this: I've never met anyone into watches who says, 'That's it, I'm good. I don't need any more.' "

This story first appeared in The Hollywood Reporter's fourth annual Watch Issue.

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