Sold it too quickly. Hesitated too long. Didn’t recognize the value. These are the lamentations familiar to all antique and estate jewelry dealers.

Dealers have a deep respect for the history and quality of the pieces they buy and sell, and they often regard themselves as caretakers of those items—so it’s natural that they may become attached. But no matter how much a dealer loves a piece, business is business.

Money isn’t always behind the regret, however. Bad luck can ruin a deal—particularly when broken ATMs or a citywide blackout are involved. Here, dealers tell us about some of the pieces and experiences they just can’t forget:

Judy Rosenbloom, The Treasure Chest, Highland Park, Ill.

There are lots of pieces that I wish I hadn’t sold, and I think that it all comes down to timing. Timing is everything—if you have something you love but the bills are coming due, and you know of someone who would really appreciate the piece, well …

The piece I most regret selling is a turquoise- encrusted eagle brooch given by Queen Victoria to her bridesmaids. It was designed by Prince Albert—who liked to design jewelry—and had a letter from the family explaining the provenance. Only 13 of them were made, and one or two of them are in museums … but at the time I really needed the money, and so it went to someone who really appreciated it. Her name is also Victoria, so she felt a kinship with the piece.

I never feel badly about selling a diamond, but it’s hard when it’s something that has a real history and story. I truly believe that, for the historical items, we are only holders of the piece, and then it moves on.

Alexander Harris, A. Harris LLC, New York

A very good client of mine sold her business in the USA for $65 million. She loves jewelry and rang me to say that she had a budget of $1 million to spend on jewelry. The great news was I had first opportunity to sell to her.

My wife and I bought two tickets to travel back early to the U.K. from our business trip in New York, as the client wanted to combine a holiday in the U.K. with her spending spree. After checking in at the JFK terminal, the power suddenly collapsed. The cell phones would not work; New York was blacked out. There was nothing we could do!

We slept in an overheated lounge, sweating the fact that we were going to lose one of the most major deals of the year. I must say it was one of the most dreadful, “it got away” deals I had ever experienced.

When we finally arrived in the U.K., we soon learned that she had privileged our rivals with her love of jewelry, and there was nothing left in the piggy bank for us.

Janet Levy, J. & S.S. DeYoung, New York

My uncle purchased the largest polished diamond to ever come out of Arkansas—it was called the Uncle Sam diamond. He had it in his case for years. He had given a number of diamonds to the Smithsonian, but somebody got him at a weak moment, and he was talked into selling the Uncle Sam. He always regretted it, because it’s truly an American treasure. We think it went to Europe, and whoever has it probably doesn’t know its history. We’re still looking for it.

Michael Haber, Michael S. Haber Ltd., Wynnewood, Pa.

It was at the Miami Beach show. Somebody brought over a Falize piece—it was either a brooch or a pendant, I can’t really remember—but since we already had a similar item, we decided to pass on it. Later on in the show, the piece was bought by my wife. She didn’t know that we had already passed on it, and she loved it.

So, we came back from the show and I threw it in a case. A guy came along who wanted to see it, but I told him that it wasn’t for sale—that my wife had bought it, and that I couldn’t sell it without her permission. Well, the guy’s wife absolutely loved it, and he kept inquiring, so I asked my wife. She said: “I bought it for me; do what you want with it.” So I sold it. The people knew what it was, knew its value, and were very happy—but my wife was so upset.

I wanted to buy her something to compensate, so I bought her a piece of Fabergé—a gorgeous ruby and diamond bracelet, with full authentication. To this day my wife has never worn it.

Diana Singer, D & E Singer Inc., New York

Back when my family business was together, we had a cameo of Medusa. It was around four inches high by three inches wide, and the relief was incredibly deep. She had this extraordinary grimace to her brow, and you could really see the anger and rage in her face, just at that moment when she was turned into stone.

At that point, I did not yet know how to distinguish between what is truly exceptional and what is pedestrian. We sold the piece during the course of business, and I will never stop regretting that I don’t have it—it got away not because I was competing with someone, but because it was too early in my career, and at that time I just didn’t know enough. Hindsight is always 20–20, and it’s always easy to regret, but we need to recognize a truly exceptional piece when we see it and have the guts to hold on to it.

Janet Drucker, Drucker Antiques, Mount Kisco, N.Y.

I’ll always remember an aluminum bracelet. It was made up of ovals, with mosaics on each oval. It looked Victorian and was very typical of a bracelet of that period. This was 28 years ago, when I first started in the business. I remember buying the bracelet, knowing that it wasn’t silver, and it was only around $20. I eventually sold it to an antiques dealer who knew what it was. Years later, I went to the Victoria and Albert Museum in London and saw that they had one just like it on display.

Joyce Jonas, Joyce Jonas & Associates Inc., New York

In the late ’60s/early ’70s, my husband was involved with the NAACP. They sponsored a show of 12 Afro-American artists, one of whom was a jeweler by the name of Art Smith. There was a necklace in true Art Smith style—an avant-garde Scandinavian look—and it was only around $500. My husband said “gold!” but I was into antiques, so I dismissed it. Later, someone offered me an Art Smith necklace that was around $9,000. So that first necklace was one that definitely got away.

Camilla Dietz Bergeron, Camilla Dietz Bergeron Ltd., New York

here are always pieces that you regret. I think of a coral suite from the ’40s—a necklace, double clips with gold and a few diamonds, and a bracelet—in just wonderful old oxblood coral. It was by Marianne Ostier, all signed.

I sold it at a profit, but didn’t make a fortune, and I sometimes think, “Oh, rats,” because I do so love coral. But the saving grace is that I sold it to a woman who has since become a dear friend, so I can visit it. And she’s also an incredibly stylish gal, so I think she’s a fantastic ad for us.

Nan Summerfield, G.G., Summerfield’s Unique & Fine Jewelry, Beverly Hills, Calif.

It was an art-deco sapphire and diamond ring. I found it at a flea market, and the seller would not take a check, so I went running to cash machines all over town—but my card wouldn’t work because the entire Wells Fargo ATM system was down.

I made arrangements with the seller to pay her on Monday, but when I got into the office on Monday, I found out that the woman had sold it to someone else later that same day!

It was a cabochon sapphire, in the most beautiful shade I’ve ever seen—and I’ve been in the business for 27 years, 13 of them at Sotheby’s. It was spectacular; it looked like you’d plugged it into a wall socket. It just glowed. And the seller was asking a price much lower than it was worth, so that one definitely sticks in my mind.

Rosie Sayyah, Rhinestone Rosie, Seattle

There was a pin that I sold on eBay for a client, and I regret that I didn’t buy it for myself. It was an Eisenberg Original, a fur clip of a boot with wings, in gold-washed sterling with rhinestones on the wings. The wings also had some movement to them—the piece was dimensional, not flat. It was from the late ’30s/early ’40s.

A figural Eisenberg Original from that collection is worth more than other pieces, so I thought it would go for more money than it did, but it sold for the reserve price of $250. It flew away!

Stevan Adler, Gems of the Past, East Hampton, N.Y.

About three years ago we sold a sautoir [a long necklace or chain], signed Tiffany, of jadeite beads with an 18k gold finial. It was 36 inches long and just beautiful. Each bead was separately carved. We found a collector right away and quickly sold it, but it was such a spectacular piece that in retrospect we would have liked to have kept it. It was truly one of a kind.

Paula Schimmel, Antique Jewels by Paula, Woodstock, Conn.

A piece that I remember very fondly was a Victorian brooch, done in enamel, with a mythological theme—it had designs of griffins. It was all done in Limoges enamel, and I remember it in design because it was just beautiful. I sold it and subsequently saw it at a later time as a brooch and earrings—they’d taken it apart. So not only am I sorry that I sold it, I’m sorry that it wound up in the hands of someone who broke it up. .

Lisa Stockhammer, The Three Graces, Houston

I found a fabulous mid to late 17th-century enamel double pendant with filigree or cannetille work around it. It was continental, and [depicted] a marvelous royal family in almost Renaissance garb.

I showed my best friend the piece and she fell madly in love with it, so I sold it to her. We’ve been friends since college, and she later came to me and said that she wanted to will the piece to me—and that I was to consider the rest of her collection as also my own, because I was the one who had gotten her started on it. “It’s mine, but it’s also yours,” she said.

So I know that I could borrow anything I love of hers, but the main thing is, she loves that piece and she’ll wear it—that’s what matters. It’s much better than keeping it locked up in a safety-deposit box!

Winona Kress, McTeigue, New York

A pretty little brooch was sent to our offices earlier this year. A lovely diamond unicorn—featuring a whimsical enamel collar, ruby eyes, and 18k gold details—was immediately recognized as having been made by the design studio of Walter McTeigue Jr., our president’s father! We offered well on the piece, and it became part of our inventory. The unique nature of the pin won it a special spot in our hearts. We nicknamed it Michael, after our president, and featured it as a signature item in advertisements. Eager to show it off, we sent the brooch to a retailer.

To say we were surprised at how quickly it sold would be untrue. It was wonderful and everyone loved it. To say we were unhappy to make a profit would also be false. We are a sales driven business. We were, however, very sad in the knowledge that this unique and beautiful brooch was no longer part of our company. It was a piece of our history. While there are several finely made items from the legacy of McTeigue that have come into our office, little “Michael” was very special.

Note: Instead of focusing on pieces that got away, an upcoming Heritage will zero in on those that won’t go away. Do you have an item that you just can’t sell, no matter how hard you try? If so, tell us about it! Send your story—and a picture of the item, if you have one—by e-mail to mclaughlin0268@ earthlink.net.