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.

Someone watching that episode who sold the same watch in the 1980s for $1,500 because they needed the money and had a different experience. 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. None of them aged well.

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Families sold these watches in the 1970s and 1980s for under $2,000 because they felt like outdated jewelry. 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.

The painful part 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.

Five-Digit Submariners

Rolex Submariner 16610. Image Source: Amsterdam Vintage Watches

The Submariner 16610 ran from 1988 to 2010. When Rolex introduced the ceramic bezel Submariner in the late 2000s, the 16610 immediately felt outdated. Families sold them in the mid-2000s for $3,000 to $4,000 because the new version looked better and the old one wasn't getting worn.

Those same watches peaked around $12,000 in 2022 and trade around $8,000 to $9,000 today. Someone who sold in 2005 for $3,500 missed a 2x to 3x return that held even after the market cooled off.

The Submariner Nobody Wanted: The Hulk

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

The 116610LV—the Hulk—was introduced in 2010 with a green dial and green bezel. For most of the 2010s, it traded at a discount to its roughly $9,000 retail price. It sat in authorized dealer cases. People passed on it because the color felt loud or trendy.

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 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 need the money. Sometimes the watch isn't getting worn. Both are 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.