Inside America’s Wildest, Most Exclusive Watch Gathering

On a rainy Sunday afternoon in a gold-tinted ballroom in midtown New York, the future of the watch market is being charted. One hundred of the most prominent, influential, and passionate collectors have flown in from 13 different countries to attend Rolliefest, a Rolex-centric, invite-only, private watch gathering, held for the first time in the U.S. this year. One collector, who asked to remain anonymous (but goes by Eberhardfan on Instagram), compares the gathering to a meeting of “all the holders of Apple stock. This really represents a very large subset of the vintage market.”

Perhaps a stronger comparison, though, is to the World Economic Forum in Davos, or the Sun Valley Conference in Idaho: gatherings where the rich and powerful sequester themselves in idyllic locales to talk empire-building over lobster. Likewise, at Rolliefest, a majority of this community’s most influential figures gather to discuss watches, put collectors onto a piece they hadn’t considered before, or blast out an underrated piece on an influential Instagram account. Their actions will have massive reverberations for the regular watch-buying public. And like a Davos or Sun Valley, Rolliefest has its own exclusive location: the Madison Room in the Lotte Palace Hotel, which glows from the gold filigree sprouting across the crown molding and ceiling and the gold satin curtains, and where what’s not made out of gold—the walls, the Romanesque columns—is marble. Over a dozen circular tables with centerpieces of white hydrangeas mounted on catalogs showcasing Phillips’s upcoming watch auction dot the room. But what sets Rolliefest apart from its competitors on the zillionaire circuit is the thing I’m most excited to see: a show-and-tell portion.

The afternoon is supposed to stick to a tight schedule. At 12:30 p.m., a lunch of eggs Benedict, “Villard avocado toast,” or smoked salmon. At 1:30 p.m., guests are encouraged to present their watches on a long table at the center of the room. Perhaps ironically, a bunch of dudes obsessed with time-keeping devices show an inability to stay on schedule. Well before the eggs are poached or the avocado toast Villard-ed, guests are unfurling their leather pouches and delicately pulling their pieces out. The person next to me, wearing a Richard Mille, carefully unpacks a Rolex GMT with a Pepsi bezel made in the early ’60s. The floodgates finally give way around a half hour later. A guest points to the table where people are prematurely beginning to set up and jokes, “They are like children who can’t wait to play with their toys.”

The toys, though, are infinite and dazzling. People in the room estimate the total value of the watches on the table to be between $50 and $100 million. There are watches with diamonds seated around the bezel, watches with dials the color of a blue sky on a perfect day, watches with puppet-green accents nicknamed “Kermit.”

But mostly there are watches made out of steel. Hundreds of them, so many that people secure red string or even a zip tie around the bracelet, like putting a ribbon on a newborn. Even though these are their babies, you can never be too sure. Because when it comes to Rolex collecting, it’s the details that matter. Did you know that a Rolex Submariner, the brand’s iconic diving watch, with the name of the model written out in red is worth two times as much as the same exact piece with the model name written out in white? That’s why you bring a zip tie.

At the head of the show-off table is a Rolex Daytona sitting on top of a laminated booklet with the words “The Red Sultan” in large font across the top. The differentiating detail on this one is a dial stamped with a symbol of crisscrossing swords. Swords! You don’t need to know anything about watches to understand how cool this particular watch is, but knowing even a little bit makes it that much cooler: Turns out it was a custom-made piece given by the sultan of Oman to a former Royal Air Force pilot. The booklet even contains pictures of the original owner receiving the watch from the sultan.

Mike Wood, a British collector and former store owner who specializes in military pieces, helps me elbow my way to a prime position on the side of the table. I pick up a a Rolex GMT Master that Wood blasts with his keychain-sized UV flashlight. It suddenly radiates like a kid’s glow-in-the-dark toy, thanks to the watch’s bezel being made from a long-out-of-production and radioactive material called Bakelite. “Finding one with a perfect bezel is so rare because they were so fragile—most of them broke, and they were replaced with metal bezels,” Wood explains. “This was probably in production from around 1954 to about 1959.” Meaning that someone blithely brought a fragile 60-year-old watch to a meet-up for anyone to grope.

Once the spout of watch stories is opened, it doesn’t shut for hours. “It feels really natural to be among the people and talk the way you can’t talk with anybody at home,” says Bernhard Bulang, who organized the very first global Rolex meet-up in 2007. “You could talk about a one-millimeter line on the dial for two hours, where normal people would say, ‘You are a fucking idiot, it's a one-millimeter line on a watch—I can’t even see it.’ ”

Wood has been attending these events since the very beginning, and this year brought “just” ten pieces—50 fewer than the record 60 he ferried to a more local “G2G,” as regular attendees refer to these get-togethers. Getting to ten was a challenge: Wood estimates he left about 990 watches at home after a months-long curation process. The criteria? He selects watches that he hopes will bring a little diversity—in other words: unique pieces others don’t have—to the table. Of course, he didn’t come here just to play with his own toys: Now he’s wearing another collector’s Rolex Reference 6062, a sparkling gold watch featuring complications that tell the date as well as the phase the moon is currently in. “This is the most complicated watch [Rolex has] ever produced,” says Wood. It’s valued at over a million dollars. That another attendee is trusting Wood with such a valuable piece goes a long way toward explaining the spirit of the event.

“It was kept very personal, very within the family, [with people who are] completely trusted, because you have to imagine we had no security—nothing—and there was easily ten to 20 million euros on the table,” Bulang says of that first meet-up in 2007. He says he was motivated to meet the people he spent hours with on budding watch forums. Bulang invited roughly 30 people to a chalet in the Netherlands to what he called the Rolex Passion Meeting, and he speaks wistfully of those early events: people dropping their most precious items on a table and then stepping away for lunch. The watch community was much smaller and more intimate over a decade ago. Today, as the number of collectors—and prices—has exploded, some have opted not to be so freewheeling with their pieces. “I would never take these five,” the prominent collector Jason Singer says, gesturing at his pristine collection, “and throw them on the table... The guys here who I know closely, I take them to my room.”

But to a man (and it is almost exclusively men, to the chagrin of a collecting community that hopes to bring more women into the fold), the attendees say that Rolliefest is a chance to meet with other passionate collectors and to learn from them. “No shit,” Singer says. “That's truly what it is.” But there are unavoidable side effects when the most passionate and fat-walleted collectors mix with professional dealers. A couple of the watches on the table have price tags stuck to them, while someone’s dropped their business card next to their watch-filled leather pouch.

And gathering just over 100 of the biggest watch enthusiasts in one place has inevitable ramifications on a rapidly growing global market. It’s still in its relative infancy compared to cars or art, and the rules are constantly rewritten. “[In the watch market,] there is no one truth or one rule,” Wulf Schütz, a dealer from Switzerland, tells me. “I've seen the truth shifting.” Today, the truth’s moving bull's-eye is centered in this room. Schütz explains that while the folks paying top dollar for watches at auction aren’t here, they are fully tuned into the people in this room. “These are the people who drive the market, make the market,” says Schütz.

Several years ago, when the watch dealer Eric Wind attended another one of these gatherings in the Netherlands, he paid close attention to what collectors gravitated toward. And crowds back then gathered around one model in particular: the Rolex Daytona “Newman.” “As a dealer, I’m always looking for what they're looking for next, because there's a herd mentality,” Wind says. “The Bali group was really into the Paul Newmans and Daytonas, so they pushed the price and they picked different references.” A few years after that meeting, the Rolex Daytona owned by Newman himself became the most expensive wristwatch ever to sell at auction. It’s not hard to draw a line between those two facts, even if it’s a tiny one-millimeter line people think you’re an idiot for talking about.

The collectors chat around the table for close to two hours, and then they sit for a panel discussion covering topics like “the economy and how it relates to our hobby,” as Geoff Hess, who organized this year’s event, says during his introduction. But the real question on the panelists’ minds is a little closer to home: What can be done to improve this “hobby”? On a weekend built around the tenets of friendship and camaraderie, Paul Boutros, head of watches for the Americas at Phillips, launches into an emotional condemnation of, well, the haters. “What’s bad for the community is backbiting, talking bad about people's watches,” he says, his microphone bobbing with every word. “Watches for our clients, for our friends, for our fellow collectors are a happy place. We come to a collectible that really resonates. Yes, because they make us happy and take us away from stress.”

Later that night at a cocktail hour, the haters are far from everyone's mind. It's time for the final event on Rolliefest’s itinerary: a lottery. A name is drawn out of a hat. This being Rolliefest, it’s not your usual giveaway: the winner will head home with a Rolex GMT-Master II (current market value: somewhere in the range of $15,000 to $20,000). When a young collector from Boston is announced as the proud new owner, the crowd breaks into applause. It sounds like an unbelievable giveaway, but in a strange twist of fate—or just par for the course at Rolliefest—the lucky winner is already the owner of a Reference 6542. Or, in layman’s terms: The guy who leaves Rolliefest with a brand new GMT already owns a much more valuable version.

Update 10/23: A previous version of this article stated that Wulf Schütz is from Germany. He is from Switzerland.

Originally Appeared on GQ