The big, small business of Kentucky Derby collectible glasses: Headless horsemen, an overrun basement and more

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Meet the husband and wife team behind over 150,000 sales of Kentucky Derby commemorative glasses

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.

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. Kentucky Derby glass from 1962. The only glass the Seilers haven’t been able to locate is from 1940.

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