The Watches Everyone Regrets Selling

Collectors love to talk about their wins. But ask them quietly, and you’ll hear the real stories—the ones that got away.

There’s always a story behind the big purchase. But sometimes, the more interesting ones are behind the big sale. The grail that didn’t stick. The watch that didn’t feel special until it was gone. Or the piece that was perfect, just not for the moment.

Watch collectors don’t talk about regret very often. But almost everyone has felt it. And if they haven’t yet, they probably will.

When You Don't Know What You Have

New York-based collector Courtney Bachrach shared a regret that wasn’t about losing something she loved. It was about not realizing what she had in the first place. In her early 20s, a boyfriend gifted her a Cartier Crash. She can’t remember if it was white gold or platinum. What she does remember is that she sold it within the year, barely wearing it. At the time, she just didn’t care for it aesthetically.

She told me, “I smugly thought, ‘I have better Cartiers.’ I had inherited a steady flow of them from my father, who was a collector. I looked at the Crash on the light pink strap and thought it wasn’t my style. I didn’t see a meaningful difference between it and the Tank Divan I was wearing at the time.”

She used the money from the sale to buy a few bracelets, and chalked it up as a practical move. But years later, that sale still nags at her. “My regret isn’t sentimental, it’s existential,” she said. “I had absolutely no idea what I was letting go of. I don’t even have a clear image to properly mourn. I wish I even knew what it was I was selling at the time.”

That experience changed how she approaches collecting. She’s far more intentional now, never selling a watch before understanding exactly what it is. She doesn’t offload gifts, and when she does sell, it’s only small, self-purchased pieces that no longer spark joy. And while she’s not typically drawn to white gold, a salmon-dial Crash in white gold has earned a spot on her grail list.

Too Much of a Good Thing

For collector Alex Lubin, the story is a little different. His regret isn’t rooted in ignorance or youth, but in owning something so good it threw the rest of his collection off balance. He once owned an Richard Mille RM 67-02 Ogier, a watch he absolutely loved. In fact, he loved it so much that he wore nothing else for 18 months. That became the problem.

“It took away so much of my interest in other watches that I had to let it go,” he told me. And once he did, he rediscovered his appreciation for variety and gained the flexibility to add pieces like a Paul Newman Daytona, which he considers far more irreplaceable than an in-catalogue Richard Mille.

His regret isn’t that he sold the RM. It’s that he needed to. The watch was too dominant, too disruptive to the joy of collecting as a whole. And still, he misses it.

Lessons From the One That Got Away

Regret in collecting doesn’t always come from a bad decision. Sometimes, it’s the right call on paper that still leaves an emotional crater. Maybe it’s a gift you didn’t understand. Maybe it’s a piece that did its job too well. Maybe it’s a trade-up that makes sense, even if the memory lingers.

Bachrach learned to wait, to ask more questions, to hold off on selling anything before she fully understood it. Lubin realized that owning fewer watches you truly love isn’t always better if it makes the rest of your collection feel unnecessary.

Collectors love to talk about the chase. But sometimes it’s the release that tells you who you are as a collector. And if nothing else, a little regret is the price we pay for knowing what matters most.