Sierra Leone tries to repeat in the Classic before he retires to stud. (Ernie Belmonte/Past The Wire)
Breeders’ Cup Closer Look
Considering the level at which trainer Chad Brown has performed for the better part of two decades in horse racing, the high praise he pours on star pupil Sierra Leone with always seems to soak up as that much more significant. In direct proportion, it will be decidedly bittersweet for the 46-year-old when he saddles the son of Gun Runner for the final time in his defense of the $7 million Longines Breeders’ Cup Classic. A winner of 19 Breeders’ Cup races and 171 Grade 1s, Brown takes a conscious moment to put his five-time winner of more than $7 million into deserved context.
“You hate to retire a horse that’s the best you’ve ever trained, of course, and as they leave your barn you worry you may never get another one as good as this one,” Brown said. “As a trainer, that’s something you have to get your head around. You hope that another Sierra Leone comes along, but there’s certainly no guarantee on that.
“He’s certainly a very rare horse—that’s the bitter part of this,” Brown continued. “The sweet part is that he’s going to the top breeding operation in the world and he’s getting a much-deserved pampered retirement where he’s going to have every chance to excel in his second career and be cared for like a king—and he’ll go home safe. For a horse that’s meant so much to you, to send him off to the best possible home for a second chapter—that’s the sweet part.”
In the spotlight since selling for $2.3 million at Fasig-Tipton’s The Saratoga Sale in 2022, Sierra Leone has long been a welcome burden of pressure for the nation’s leading trainer, with undeniably lofty expectations. Owned by Peter Brant, Mrs. John Magnier, Michael Tabor, Derrick Smith, Westerberg and Brook T. Smith, the blue-blooded bay has gone to post as the favorite seven times in 13 starts, including the Travers (G1) and Belmont (G1). Only twice have his odds been north of 2-1—his head loss in the Kentucky Derby (G1) at 9-2 and his triumphant Classic last year at 6-1—while rewarding connections with a trio of Grade 1 tallies, including last year’s Blue Grass (G1) and this year’s Whitney (G1).
ICYMI: Sierra Leone out at @DelMarRacing looking like he’s done this before pic.twitter.com/OYhNrffMpR
— Breeders' Cup (@BreedersCup) October 28, 2025
“He’s taught me a lot,” Brown explained. “You feel, as a trainer who has been doing it long enough at a high level in races like the Kentucky Derby and Breeders’ Cups, like you’re really prepared to handle any sort of situation. Then you get a horse like him and realize there’s even more to learn and experience. I feel like, as we close out his career, like I learned a lot from him to use going forward. The Derby is such a hard race to win and I think that managing a horse of his caliber, I learned a lot and I think that we did really well—but also there’s always little things you can go back and say, ‘man, I can use this little nugget of information to improve in a couple little areas,’ of course.
“For a horse who’s never been off the board and been so sound and healthy while being managed under a microscope and a lot of pressure, I feel a lot of gratitude and accomplishment for me and my team,” he continued. “I feel like we did a really fine job and as good as anyone could have done with him. Some things in racing and in sports, unfortunately, are always going to be left to luck and circumstance and there are so many factors, especially with horses. All the intangibles and human elements on the field of play, when you look at what we have done with Sierra Leone, I know we did the best we could to put him in a position to perform every time. I think we accomplished that.”
