Teddy Baldassarre
The Most Expensive Rolex Watches
Admit it, you’re here because you googled “Most Expensive Rolex Watches” in the hopes of gathering up some horological bar trivia, right? No? You say you’re here because you really, truly are interested in buying one of the most expensive watches Rolex currently puts out? Well, good news. We’ve updated this article to incorporate both. Photo: Sotheby's Founded in 1905 by Hans Wilsdorf, Rolex is today the most globally recognized Swiss luxury watch brand, one of the leading innovators in the watch industry from the 20th Century to today, and the maker of some of the most popular and coveted watch models in the world, from gents’ classics like the Datejust and Day-Date to sport-luxury icons like the Submariner, Daytona, and GMT-Master. As one might expect with such a horological pedigree, Rolex watches have also become some of the most valuable watches on the secondary and auction markets, with the most elite and exclusive pieces selling for $1 million or more. (Disclaimer: obviously, for the most avid and well-connected Rolex customers, it is the legendary “off-catalog” models - like the "Rainbow Daytona" pictured above - that both project the most mythical aura of exclusivity and command the most stratospheric prices. The problem with accurately reporting on which of them is really the “Most Expensive” is built into their rarity: such models change hands without an actual MSRP ever being declared publicly, and whatever that original purchase pric...