The Rolex Watches People Regret Selling

A U.S. Air Force veteran named David bought a Rolex Cosmograph Daytona for $345.97 in 1974 at a base exchange. He stuck it in a safety deposit box and barely wore it. In 2020, on Antiques Roadshow, an appraiser valued it between $500,000 and $700,000. When David heard the appraisal, he fell to the ground.

David kept his Rolex. A lot of people didn't.

Anyone watching that episode who had sold the same watch in the 1980s for $1,500 had a very different reaction. So did the person who sold one in the 1990s for $5,000, or in 2005 for $15,000. All of those sales felt reasonable at the time, but unfortunately, none of them aged well looking at today's market.

The painful part, and also the reason no one should beat themselves up about selling a watch 30+ years ago, is that nobody could have predicted this. The vintage Rolex market did something unprecedented in the 21st century. It's easy to look back and point out what someone should have done, but at the time, selling felt logical. Still, it's fun to look back at the low prices these watches traded for, often not that long ago.

The Daytonas That Nobody Wanted

Early manual-wind Daytonas, references like the 6239, 6263 and 6265, sat in dealer cases for years in the 1960s and 1970s. Rolex couldn't move them. Chronographs weren't popular. The exotic dials that later got branded "Paul Newman" were even harder to sell.

Rolex Daytona 6263 Exotic 'Paul Newman' Dial. Image Source: Rob's Rolex Chronicle

Families sold these watches in the 1970s and 1980s for under $2,000. A 6263 Daytona sold in 1985 for $1,200 would trade for $75,000 to $150,000 today in standard condition, or $400,000+ with a Paul Newman dial and strong originality. Even after the 2022 market correction, these watches are worth 50 to 300 times what people got for them decades ago.

Five-Digit Submariners

Rolex Submariner 16610. Image Source: Amsterdam Vintage Watches

The Submariner 16610 ran from 1988 to 2010. Its retail price started around $2,500 and climbed to $6,000 by 2010. Solid pre-owned examples traded below $5,000 all day in the '90s and early 2000s. When Rolex introduced the ceramic-bezel Submariner Date 116610LN in 2010, plenty of owners sold theirs for $5,000 or less.

Those same watches peaked around $12,000 in 2022 and nice examples trade around $9,000 to $10,000 today. Someone who sold in 2010 for $5,000 (~$7,700 adjusted for inflation) missed out on a nice gain that held even after the market cooled off, not to mention a handsome 5-digit Sub on their wrist.

The Submariner Nobody Wanted: The Hulk

Rolex 'Hulk' Submariner 116610LV. Image Source: Hodinkee

The 116610LV, known as the Hulk, was introduced in 2010 with a green dial and green bezel. For much of the early 2010s, it traded below retail (~$7,500-$9,000 over its production). It sat in authorized dealer cases. Perhaps the color felt loud or unwearable at the time, perhaps the lack of enthusiasm around the watch was a self-fulfilling prophecy for a while.

Interest picked up around 2017. When Rolex discontinued it in 2020, it traded around $14,000. By early 2022, it peaked near $30,000. Today it trades around $17,000 to $20,000. Someone who sold a Hulk in 2015 for $7,000 to $8,000 (~$10k adjusted for inflation) because it wasn't getting wrist time can see it trading for more than double that today, even after the correction.

The John Mayer Effect

Rolex 'John Mayer' Daytona 116508. Image Source: Wind Vintage

The Daytona 116508 with the green dial is a yellow gold chronograph that became its own case study in 2019. John Mayer brought one to Talking Watches and described his approach: look for objective value in current-catalog models that aren't hyped up yet.

He sort of spoke it into existence. Before that episode, the 116508 green dial traded close to its $34,650 retail price. Someone who sold theirs in 2019 or early 2020 for $40,000 to $50,000 watched it peak around $110,000 in 2021-2022. Today it trades around $65,000 to $75,000. Still 50% more than what they got, but the real sting is selling right before celebrity endorsement took off.

Rolex 'Double Red' Sea-Dweller 1665. Image Source: HQ Milton

The pattern holds across decades and references. Watches get sold when they feel ordinary, outdated, or just not worth keeping. Then the market decides otherwise. Sometimes you want to buy a new watch and you have to sell something. Sometimes a watch simply isn't getting worn. These are all valid reasons to sell. But if it turns sour a few years or decades later, try not to beat yourself up. You’re certainly not alone.