We Talked to 14 Collectors About the Watches That Got Away

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Ask a watch collector what falling in love with a wristwatch is like and chances are, they’ll say it’s a lot like falling in love with a person. The timepiece gets under your skin—so much so that you can hardly think about anything else. Sometimes the love is unrequited, and you find yourself pining for the watch from afar. Other times, the love affair comes to a bitter end for reasons beyond your control. In many cases, the collector is left reeling, and schemes to get the watch back.

To understand the relationships collectors have with their watches, we asked a slew of them to tell us about “the watch that got away.” The stories were humorous and poignant, regretful and filled with silver linings. In all cases, the stories helped distill a valuable piece of wisdom about not just watch collecting, but also life in general. Collector Fred Savage told us that his watch-that-got-away story “has shaped the way I’ve approached watches ever since, not so much because of the watch itself, but because of the lesson learned.”

And therein lies the point. In the end, it’s not the watch you remember most—it’s what it taught you, as made evident by the 14 stories below.

Fred Savage, founder, Timepiece Grading Specialists, Dayton, Ohio
“After waiting and looking for just the right Rolex 1803, my dream example ended up in the case of Wanna Buy a Watch, my go-to vintage watch store in Los Angeles,” Savage says. “It was perfect: just enough wear to tell a story, creamy lume plots, original owner provenance. It was everything I had been looking for. Each time I would visit the store, I would run to the case just to admire how perfect this Day-Date was. It was thrilling to see it, to try it on, to admire it, to know that with one swipe of a card, it could be mine. One time I went to the store and, to my astonishment, the watch was gone! It had vanished! When I asked where it was, Ken Jacobs, the inimitable and endlessly quotable proprietor of Wanna Buy a Watch, not-so-gently informed me, ‘Hey Fred! This isn’t a museum!’ And that’s when I realized I had been ‘visiting’ the watch at a store that existed to sell watches! It’s easy to forget that sometimes. Now I know that unless I’m ready to buy a watch, there’s absolutely no reason to expect it will be there the next time I walk into the store. The moral of the story: Buy! I’m haunted far more frequently by the watches I didn’t get than by the ones I did.”

Eric Wind, owner, Wind Vintage, Palm Beach, Fla.
While Wind was pursuing his Master of Business Administration degree at Oxford University in England in 2012, he purchased a rare Heuer Skipper reference 7754 from the family of the original owner. “Of course, the degree was expensive and I had a collector friend hot on my heels for the watch, so I sold it to him for $9,000,” Wind says. “I thought I could probably hunt and find a better example in the near future.”

Fast forward a couple years, and the watch had earned a nickname, the “Skipperera,” and was valued at over $70,000. “I had major seller’s remorse, but I don’t regret getting my MBA at Oxford!” Wind says. “Life goes on and I am happy my friend got my watch and still has it.”

David Bahng, real estate executive, Los Angeles 
“Over the last 35 years of my watch-collecting journey, I’ve been fortunate enough to have only two ‘watches that got away.’ Both were heartbreaking instances. On March 7, 2011, I was getting my safe and its contents ready for the last items to be moved to our new home. Upon opening my safe, I discovered the main pieces of my collection were gone/stolen: a Rolex Day-Date in white gold that was a 40th birthday gift and a piece to mark my business start-up having its first profitable year; a Rolex Submariner Date in steel, which marked the birth of my daughter; and a Rolex GMT-Master II in steel, my travel companion.

“Then, on March 16, 2020, the day L.A. shut down in an effort to slow the spread of Covid-19, I called my trusted vintage dealer to consign my Patek Philippe 3970P (platinum perpetual calendar chronograph) in preparation for a tough financial future. It sold quickly and I have yet to replace it because the value of the piece has gone up significantly post Covid.”

Yan Gee (a.k.a. @Yandretti), crypto investor, New York City

In October 2022, Gee bought himself a 36th birthday present: a Rolex Datejust 36 with a green palm dial on a Jubilee bracelet. He purchased it through a gray market dealer “at the height of Rolex’s pandemic-inflated prices,” and paid $11,500, he says.

An ardent collector of esoteric watches, especially those from independent watchmakers and microbrands, Gee had taken a four-year hiatus from collecting, and this piece marked his return. But last year, Yan decided to sell the watch for a break-even price in advance of “an expensive trip to Brazil,” he says. 

Almost immediately, he regretted the sale. To add insult to injury, the model was discontinued two weeks later. “Rolex has had three unique dials in the last five years,” Gee tells Robb Report. “This palm dial, the puzzle dial Day-Date, and the Celebration dial Oyster Perpetual, so this green palm dial is a very special piece. One day I might consider looking into getting one again.”

Matthew Price, founder, Kinser Creative Agency, Los Angeles

“I’ve always wanted a little gold Patek Philippe Calatrava. It’s part of my retirement fantasy where I become a leathery old man living on a golf course somewhere near the equator and split my time between the pool and the course. The problem is, I bought the retirement watch too early, and in my 30s, I still run into walls, fall into puddles, and get hit with skateboards. Sadly, I do not live the life required for such a delicate watch, so I sent it down the line to the next owner. I still think about it regularly and hope that one day, when I am ready for a life of seersucker-clad leisure, it will find its way back to me.”

Henry Flores, founder, Classic Watch Club, New York City
“The watch that I regret selling the most was my 1665 Mark IV Double Red Seaf-Dweller. I sold it because I was renovating the Maverick, my midcentury modern home in Woodstock. I will eventually buy another DRSD, but for now sharing this beautiful home with my friends and family was well worth it. (Also, selling the DRSD enabled me to purchase my first AP, which I still own and love.)”

Richard Rogers, watchmaker, Los Angeles
“Twenty years ago, at the Alameda Point Antique Faire, I spotted a round Patek in a steel case. I offered $2,250 and purchased the watch. When I got back to my shop and examined my find, I discovered it was a ref. 565 in very good condition. I serviced the movement, doing nothing to the case, and began to wear it. I thought that maybe I’d just keep it. Then, a friend I’d shown it to told me some guy in Missouri would give me $18,000 for it. Ok, I thought, maybe I didn’t like it that much. I ended up selling it to him. A few months later, the same friend calls me and tells me to check the results of a recent Sotheby’s auction. While it wasn’t the same watch, the only major difference was that this one had just sold for $68,000. Lesson learned.”

Chase Pion, cofounder and CFO/COO of pre-owned watch marketplace Bezel, Los Angeles
“I have a ‘watch that got away’ story that actually has a happy ending. I was looking at a 1980s Audemars Piguet Cobra Day-Date model that popped up on Bezel, an all-yellow-gold 5587BA that you don’t see very often. Our first employee was a director of private watch sales at Sotheby’s. He’s like a prodigy in watches, and I was like, ‘All right, Ryan. Should I buy this watch?’ And he said, ‘Yeah, it’s a pretty cool watch. It’s very under-appreciated.’ So I went to buy it, and it had sold like three hours before. I was so bummed. For a while, I kept thinking, ‘Oh, I totally blew it.’ But four or five months later, another one popped up in a better dial configuration, and I was able to buy it immediately. The moral of the story is that you probably don’t realize how much you wanted something until you missed it.”

Paul E. (a.k.a. @aircooltime), healthcare executive, Colorado
“This was a rare Rolex 1675 ‘double Swiss underline’ example that came to auction during a good time to buy in the market compared to the recent past. I did my research and prepared to bid. During the auction, I waited for just the right moment to submit my bid online and ultimately was the underbidder when the lot hammered. When I heard the auctioneer announce the name of the city where the winning bidder was based, I wondered if it was someone I knew and later confirmed it was won by a respected fellow collector. That helped ease the pain of disappointment from missing out. The silver lining for me was realized when this fish that got away allowed me to ultimately obtain a much rarer steel Patek 2508 later that month, a watch that captured my attention for some time. Thankfully, all ended well!”

Erik Slaven, U.S. editor for Monochrome Watches, Los Angeles

“I’ve been a watch enthusiast for decades. As a professional writer for Monochrome Watches, I have access to a lot of brands and it’s helped shape my preferences over time. I like a vintage Rolex Explorer like the next guy and it’s fun to yearn for heavyweights like a Vacheron Constantin Overseas or Breguet Classique 5177, but well-executed and affordable pieces by smaller brands tend to impress me the most. A watch that I really regret selling is the original Farer Stanhope (from British watchmaker Farer) with a compact cushion case and unique piqué textured dial in white with dark blue and red accents. It was hand wound and had a funky personality, and although there’s a sequel with the same dial, the case has grown a bit with a different design. Cool, but not quite the same. Such is life.”

Morgan King, real estate executive, Los Angeles

“I should have kept one of the Rolex Paul Newman reference 6239 Tricolor models. At one point in my collection, I had three of them. They were all different and special and I loved them all. Sadly, the 6239 reference was a pump pusher chronograph and I felt they were too small to wear. I ended up trading them for other pieces now in my collection, like the 6541 Milgauss and the 6538 Big Crown. This was before Paul Newman’s Paul Newman went on sale. Man, oh man…. I should have kept one in my collection.”

Jarrod Cooper, founder, Neighborhood Watch Club, Los Angeles

“I’ve been fortunate to collect many exceptional watches over the years. In 2016, I began considering a more significant addition to my collection. I initially had my heart set on a Lange 1 until Josh at Govberg suggested I look into F.P. Journe. At the time, the brand was quite rare, especially in Australia, where I am from, so I hadn’t seen one in person. However, I was captivated by the design and followed his recommendation to acquire a Réserve de Marche in platinum.

“From that moment, I was completely drawn to the brand, eventually adding a few more pieces, including a remarkable [Chronomètre Bleu] Byblos. My appreciation for F.P. Journe deepened when I had the opportunity to own a one-of-a-kind Chronomètre Optimum. I truly believed this was a watch I would keep forever.

“However, due to the need for funds for my U.S. business visa, I had to make the incredibly difficult decision to sell this special piece. It was a very tough choice, especially considering the rarity of owning a one-of-a-kind F.P. Journe.”

Gary Copeland, cofounder and CEO, Wulver Advertising Agency, Los Angeles
“There’s a small vintage watch shop tucked away near my wife’s aunt’s home in Rome. About 10 years ago, this dealer had a 37 mm rose-gold vintage Vacheron Constantin dress watch from the early 1960s sitting in his window. Watches from this era rarely came in sizes larger than 34 mm or 35 mm, so collectors have dubbed larger versions ‘jumbo.’ They are rare to say the least. I’ll never forget that dial. Stunning doesn’t begin to cover it. And those cow’s horn lugs? Damn! For a Vacheron collector like myself, pure perfection. 

“At the time, I didn’t have the money for it. Standing there, I knew with absolute certainty that I would never see another one like it—certainly not in that condition, and most certainly not at that price. I held it. Tried it on. Lamented at what I knew would be a missed opportunity. That was 10 years ago. I’ve been thinking about that one Vacheron ever since.”

Rajan Mac, accountant, Los Angeles

“My lifelong desire to always wear a watch came from my father. He was from a generation that thought a watch was necessary to go about your day and move through the world.  He always wore a watch, one or two gold rings, a gold necklace, and Jovan Musk as his signature scent (it worked for him and no one else). It sounds very bling, but on him, all his objects were very understated.

“He wore a gold-plated quartz Seiko with a square dial on an integrated bracelet. My father got the watch in the ’70s in Hong Kong. In those days, he told me, Seiko was the in brand, so, as a young man, he wanted to be in vogue and make a statement. Once he got the watch, it never left his wrist except to shower. As I grew up, I associated watches with my father and thought of them as an important accessory for men’s daily wear.

“As time went on, my enthusiasm for watches grew and I wanted to share this with my father and show him a whole world outside of Seiko. Unfortunately, during that time, age and illness took hold of him. As he went in and out of hospitals and nursing homes, his beautiful Seiko got lost in the ether, never to be found. This watch is the one I have the greatest desire to own, far beyond any luxury brand. It represents time, place, style, and the person who was my biggest champion in life. Maybe one day.”