The Athletic has live coverage of the 2024 Kentucky Derby, the 150th anniversary.
PROSPECT, Ky. – Amy Seiler is sitting in a coffee shop, leafing through a catalog and discussing a headless horseman. The decapitated rider in question was not chasing the Ichabod Crane of lore; rather he was hunched over his horse in pursuit of an unseen finish line. Etched onto the side of a drinking glass in 1956, courtesy of a factory production error that failed to give the man his dome, the headless jockey turned an ordinary keepsake into a valuable commodity.
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When it comes to the Kentucky Derby, the egg and the chicken arrived in tandem. Noticing that visitors were swiping their decorative drink glasses after race day in 1938, Churchill Downs wisely decided in 1939 to create (and sell) commemorative drinkware, opting to fill the vessels with a favorite libation: the mint julep. Not so surprisingly, drink sales spiked and a tradition — at a race already steeped in traditions — was born.
Each Derby is now memorialized in a uniquely designed glass that has but one requirement: a list of all of the previous winners. For most people, the glass is a trinket to perhaps display on a bar shelf, but the combination of rarity and scarcity has also created a demand among niche collectors.
Which is where Amy and the headless horseman come in.
In 2008, she and her newlywed husband, Michael, were looking for a way to make a little extra cash. Michael owned a UPS store and Seiler worked in public relations. She’s an avid horsewoman, turning a childhood spent riding in the local pony club into a grown-up commitment to retraining retired thoroughbreds. Though not a Louisville native (Seiler grew up in Ohio), she’s lived there long enough to be well-versed in the Derby, and has watched as the race has grown in popularity thanks largely to its explosion in pop culture.
As the Seilers considered their “side hustle,’’ as Amy jokingly calls it, the Derby market made sense. Glasses, they realized, were ideal – commemorative, collectible and best of all, easy to ship. They found the headless horseman from 1956 at an antique market, put it on eBay, turned a handsome profit and launched themselves a full-time career.
In the 15 or so years since, Amy estimates they’ve sold more than 150,000 glasses. The Seilers long ago stopped haunting antique malls and flea markets, instead building out a website, derbyglasswarehouse.com — even though they aren’t technically a warehouse. Instead the Seilers are more like brokers, finding and buying collections from people with glasses and nowhere to use them, and selling them to people whose collections need missing pieces. On occasion their basement does take on the feel of a warehouse, with new glasses stored for resale, but rare finds have short shelf lives and typically jump from seller to buyer automatically. “We have a wait list of at least 10 or more people almost all the time,” Amy says. “We also have a lot of repeat customers.”
Amy is now something of a Derby glass historian, able to page through the catalog she’s created and offer tidbits and insight on the backstories of the drinkware. A full collection, Amy estimates, will run a person upwards of $100,000. Supply and demand are the driving force behind the pricing, so naturally the older the glass and the harder it is to find, the more valuable it is.
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The first editions, from 1938 and 1939, are especially appealing, as are glasses made during World War II. Due to war rationing and shortages, Churchill Downs went to a company that was closing and bought up all of their drinkware made out of what’s called beetleware – like a plastic or acrylic material that looks more like a mottled mosaic instead of clear glass. Those sell for at least $5,000.
The only glass the Seilers haven’t been able to locate is from 1940. There is nothing significant about it in appearance – it’s red and blue designed – but the print runs for glasses are only done once. Today that equates to about 700,000 glasses in circulation; in 1940, only 800 were made. One sold at an auction recently for $39,000.
But other quirks add value, too. Along with the headless jockey, some of the ‘56 collection was printed with tail-less horses, and others with horses with three tails. “I don’t know what they were doing in that factory, but there were a lot of mistakes,” Amy says. “Apparently they had no quality control.” In 1974, manufacturers made another error – listing ‘71 winner as Canonero, instead of Canonero II. More than 400,000 were printed before the mistake was discovered, turning the typos into a treasure.
As unique as the stories behind the glasses, the Seilers have found the sellers and buyers have their own unique tales, too. Thanks to the website’s popularity, most people reach out to the Seilers, looking to offload their collections. They’ll ship them with notes, explaining their history. A group of friends who rented a bus from Chicago to Louisville for the Derby each year boxed up vintage postcards along with the glasses they’d collected over the years, writing out notes about each of their visits. Just recently Michael flew to Arizona to meet with a woman who had a pretty significant collection. It belonged to her mother, who grew up in Louisville, the child of Derby-loving parents who loved to throw race day parties. The seller’s parents, however, had passed and she no longer wanted the glasses. They’ve since moved on to good homes. “It’s great to see them live on,” Amy says. “They’re a piece of history.”
Much to the Seilers’ surprise – and delight – there seems to be no end in interest in the glasses. As older generations pass, the couple is finding more and more children looking to part with collections, and as bourbon and the Derby become trendier, more and more people looking to buy. Business is booming enough that Michael sold the UPS store in 2021.
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The irony in all of this? Among the least interested in collecting are the Seilers themselves. Amy is a self-described minimalist, and has felt no compunction to keep any of the treasures for herself. She happily loans glasses out for fundraisers – the Adopt Me! Bluegrass Pet Rescue regularly uses them for their annual bourbon tasting event – and has, in a delicious twist, used the funding to feed a glass-related personal passion: horses.
Amy found special joy in giving new life to retired thoroughbreds, taking in animals who had sustained non-catastrophic injuries and rehabbing them into new opportunities. One, a mare named Eagle-Eyed Lady, arrived with pins in her ankle and leg after a fracture; Amy retrained the horse and returned her to her owner.
But post-COVID she decided to take a step back from that added responsibility. She did not exactly divest herself from horses. Instead she passed on her equine passion to her 7 1/2 year old daughter, Abigail. Abigail had been itching for a pony for years, but Amy and Michael pushed her off, waiting until she was a bit older and could understand the work that came along with it.
This fall Abigail got her wish, a pony named Bella Luna. “We purchased the pony with the money from one of the collections we had come in,” Amy says. “Kind of a really nice full circle.”
GO DEEPER
Ghosts of the Kentucky Derby: From Lewis & Clark to the race's near demise
(Photos by Leandro Lozada, graphics by Drew Jordan, lede image by Eamonn Dalton)
