Jim Lai’s first vintage Rolex was a bad buy—now the world’s top dealers ask for his opinion

The second: a 1963 black dial Rolex Daytona, aka the “Le Mans”. It predates the Daytona name and is instantly recognisable for its double “Swiss” signature, a quirk Lai delights in explaining. In the earliest examples, Rolex printed “Swiss” twice at six o’clock: once in its usual spot above the lume dot, and again just below, in smaller text, barely peeking out beneath the rehaut, or inner bezel, due to an overlap of dial and case specifications during production. The result was a rare dial detail, sought after by collectors who appreciate the analogue beauty of manufacturing mishaps.“My friend in Taipei has the white; I have the black,” he says, laughing. “Sometimes we meet and pretend to negotiate a swap but neither of us will ever let ours go. The jokes make the friendship last.” He acquired the Le Mans from the same seasoned US dealer as his Subaqua, after years of watching lesser examples come and go. “This one, the dial is untouched, no major scratches— perfect for its age. It’s one of those you treat with utmost caution; only a few master restorers in the world would dare touch it.” 

Then there’s a Rolex reference 6244, known as “the star”. This is a small, 32mm oddity from the 1960s, notable for its star-shaped dial markers. “At gatherings, people always notice this,” Lai says. “Why so small? In those days, it was all about understated elegance.” His star-dialled Rolex is one of perhaps ten surviving, and he is quick to point out the importance of keeping such pieces immaculate. “They aren’t waterproof, so if one’s survived all this time with the dial intact, you know it’s been loved. When I show it at events, even major collectors say, ‘What is that?’”

Finally, he speaks about the tropical dial Rolex Submariner—a once-black watch whose dial has bloomed into shades of brown under decades of sunlight and gentle wear. “Fifteen years ago, I started selling some [tropical dial Rolex watches] to friends,” Lai says. “But I always kept tabs ... I even bought a few back later. A tropical dial is nature’s limited edition, and every time I see one, I think about the sunshine, the long storage in company basements—chance and time doing what no factory ever could”.

Lai’s collecting is driven by narrative, not numbers. “Each vintage Rolex has a great story; every piece passes through lives, families, with a story at each branch.” Advice to fellow collectors is clear-eyed, generous and quietly heartfelt: “Test-drive the watch, see how it feels—especially at today’s prices. Above all, don’t buy thinking you’ll flip for profit. Buy only the best you can afford and let the stories find you. Collecting is [about] luck and patience, not just money.”

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As our afternoon at Carlyle & Co winds down, Lai’s shares some of the best advice I’ve come across: “Collect only the best—not just the most expensive but those that hold meaning, those with a story. And remember—every scratch is yours, every watch has lived, and every dealer you trust becomes part of the collection.” This wisdom, fortified by humour and decades of devotion, is what makes Jim Lai the heartbeat of Hong Kong’s watch collecting community—a guardian of not just watches but also memories.

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