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 this year in the US. 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 idyllic location: the Madison Room in the Lotte Palace Hotel, which glows from the gold filigree sprouting across the crown molding and roof 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’ 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 watch’s 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.

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