Calvin Borel's Triple Kentucky Derby Saddle, Trophies Hit Auction Block

Three Kentucky Derby trophies and the 28.5-ounce Merlano saddle Calvin Borel used to win all of them landed on the auction block at Lelands, giving collectors a window through April 18 to own a piece of the most concentrated Derby dominance any jockey has produced in the modern era.

The saddle is the centerpiece of the lot. Crafted in glossy black leather and measuring 16.5 inches back-to-front and 9 inches wide not including the flaps, it carries "C. BOREL" in white paint pen on the underside along with the faint remnant of Borel's signature. Edge fraying and race-use creasing show up in the Lelands catalogue description, and neither is listed as a flaw. For provenance-conscious collectors, those details are exactly the corroboration that separates a verified race artifact from a shelf piece.

The trophies map directly to Borel's three Churchill Downs masterclasses: Street Sense in 2007, Mine That Bird in 2009, and Super Saver in 2010. Each opened for bidding at $2,500. Of the three, Mine That Bird remains the most staggering entry in Derby lore. Borel guided the 50-1 longshot, trailing by as many as 21 lengths in a field of 19, through a gap along the rail that most jockeys would not have seen, let alone attempted. The horse won by 6¾ lengths, the largest winning margin in 63 years and the second-biggest upset in Derby history. Borel had won the Kentucky Oaks the previous day, making the 2009 stretch arguably the two most remarkable back-to-back days any jockey has ever put together at Churchill Downs.

Lelands framed the lot around Borel's signature technique, describing his "fearless, rail-skimming style and uncanny feel for the Kentucky Derby" as central to his legacy. That framing holds up analytically. Borel did not simply win three Derbies on talented horses; he found paths along the inside that other jockeys left untaken and squeezed results out of scenarios that looked lost. The Mine That Bird ride, with the horse dead last past the half-mile pole on a sloppy track, is the clearest example.

The auction is part of Lelands' broader 2026 Spring Classic sale, which lists more than 1,400 items including a 1914 Boston Braves World Series ring and Shaquille O'Neal's 1992 John R. Wooden Award from his LSU season. In that context, the Borel lot stands out not for spectacle but for specificity: three trophies, one saddle, three verified Classics, one jockey, and the kind of physical provenance that makes a memorabilia case easy to close.

The bidding closes April 18. What the final hammer prices say about where Derby artifacts sit in the broader sports collectibles market will be worth watching. A saddle that won three Roses has no obvious comparable sale.