On Monday, September 28th, Rolex and Phillips will auction four Rolex Daytonas, dubbed “The Four Seasons,” in London. The Daytona, Rolex’s famed 1960s racing chronograph, is a regular auction feature, with collectible models like the “Paul Newman” and “John Player Special” often fetching millions, but this sale will be a very different affair. For one thing, the Daytonas offered for sale are brand new. For another, they’re each one-of-a-kind. And for yet another, they’re to be sold as a set. Every aspect of this sale is unusual, but following the surprise launch of the Rolex Padellone last week, we are beginning to expect the unexpected from Rolex (which is an unexpected turn in itself).

As most Rolex fans know, beyond its standard catalog of watches, the brand has a secret menu accessible only to its most elite clientele. These pieces, usually highly bedazzled versions of high-end models like the Day-Date and the Daytona, are the ultimate grails for the world’s most dedicated (and deep-pocketed) Rolex collectors, and they let the brand show off its skill with gem-setting and stone dials. Unlike the mainline collection, which you can buy at authorized dealers, these are sold by application only.

Rolex doesn’t publish prices for off-menu pieces, but they’re believed to sell well into the six-figure range and can easily fetch half a million dollars on the secondary market. (And that’s for serially produced pieces like the “Eye of the Tiger,” not one-offs.) This year’s off-menu releases included The Four Seasons, four one-of-a-kind Daytonas, nicknamed for their colourful gem-set cases and dials designed to evoke Summer, Fall, Winter, and Spring. Rolex displayed these under glass deep inside its booth at Watches & Wonders Geneva last April, and while photography was strictly forbidden, a Rolex staffer told us they’d be priced at about 4 million Swiss Francs (or around $6.8 million Canadian loonies).

According to Hodinkee’s Ben Clymer — a reliable source for industry gossip if ever there was one — Rolex had asked its dealers to submit a list of clients who might be interested in such a purchase. When that list topped 1,000 names, the rumour goes, Rolex decided to take a different approach and hold a charity auction instead. Monday’s auction will benefit charities overseen by two of Rolex’s most famous endorsers, The Federer Foundation, Roger Federer’s charity benefiting children in Africa and Switzerland, and Re:wild, Leonardo DiCaprio’s environmental conservation initiative. Now the question on every watch aficionado’s mind is just how much these spectacular pieces will rake in.

The highest price ever paid for a Daytona was US $17.8 million for Paul Newman’s “Paul Newman” in 2017, and that was only a single (albeit very famous) watch. According to Clymer, he’s aware of more than one offer for US $10 million ahead of the auction announcement, and if that’s where bidding starts, there’s truly no telling where the hammer will fall. Rolex has produced few one-offs in its history, and has never offered them directly to the public before. Add in the Daytona’s reputation as a blue-chip investment, and the charitable aspect (which would make the sale a tax write-off for the buyer), and things are bound to get spicy. In the meantime, one thing is certain: there’s never been a more interesting — or unpredictable — time to be a Rolex fan. Learn more