As Keeneland’s September Yearling Sale kicks off on Monday, September 14, a well-known presence will be absent from the auctioneer’s podium. Scott Caldwell, who has been a key figure at this premier Thoroughbred racing auction for over five decades, has decided to retire. This marks the end of a remarkable family legacy with Keeneland that dates back to the 1950s with his late father, Tom Caldwell, and includes his late brother, Cris.
Scott, now residing in San Clemente, California with his wife Leslie, is eager to devote more time to his family and personal interests like bowhunting and swordfishing. He humbly cites another reason for stepping away from the sales. Reflecting on his extensive global auctioneering experience, Scott admits he wanted to avoid overstaying his welcome. He prefers to leave with people remembering his positive contributions rather than feeling relieved by his departure.
The Caldwell family’s involvement with Keeneland began in 1957 when Tom Caldwell served as assistant to famed auctioneer George Swinebroad. Scott started his Keeneland journey in 1974, having previously auctioned livestock at the family’s California stockyards. After Swinebroad passed in 1975, Tom ascended to Director of Auctions at Keeneland, a role he held until his death in 2001. Cris followed, working as an auctioneer there until his passing in 2020.
Tom Caldwell was considered a gentle giant by many, according to Scott, but he was also demanding of loyalty and work ethic. He taught Scott and Cris an important lesson: the auctions aren’t about the family or the company—they are about the horses. Scott emphasized how critical it is to maximize the seller’s return on every horse, regardless of its price point, often pushing hard to secure every extra dollar for consignors.
Throughout his career at Keeneland, Scott auctioned numerous future stars, including the 2016 September Sale colt Justify, who went on to win the Triple Crown. Looking back, Scott wonders if even more could have been achieved for Justify’s price, knowing the consignor well and thinking the colt’s later success could have fetched a higher bid.
Although retiring from Keeneland, Scott will continue auctioneering at smaller events in California, including car sales with CarMax and upcoming American Quarter Horse yearling sales at Los Alamitos. Still, Keeneland will remain close to his heart, and he expects to feel emotional when staying connected with the Keeneland team, praising everyone from auction staff to those who maintain the grounds.
Tony Lacy, Keeneland’s Vice President of Sales, acknowledged the Caldwell family’s profound impact on the auction’s history. He highlighted their essential role in elevating Keeneland’s auctions to world-class status and expressed pride in working alongside Scott, wishing him and his family all the best.
Scott and Leslie, married since 1973, have two sons—Ramsay and Kenny—both automobile auctioneers, and four grandchildren aged 12 to 21. Ramsay once worked as a Keeneland auctioneer and recently served as a bid spotter at a major sale.
This piece was originally published by Paulick Report on September 10, 2026.
Fan Take: Scott Caldwell’s retirement closes a significant chapter in Keeneland’s storied auction history, marking the end of an era shaped by unparalleled dedication and expertise. For horse racing fans, this transition is a poignant reminder of the deep human connections behind the sport’s business side and marks a moment to celebrate the legacy that has helped shape the future of Thoroughbred racing.
Source: sports.yahoo.com
