Sierra Leone tries to repeat the Classic before calling it quits. (Ernie Belmonte/Past The Wire)
A closer look at Breeders’ Cup
Considering the level at which trainer Chad Brown has performed in horse racing for the better part of two decades, the high praise he showers on star pupil Sierra Leone it always seems to be much more important. In direct proportion, it will certainly be bittersweet for the 46-year-old as he saddles the son of Gun Runner for the final time in defense of the $7 million Longines Breeders’ Cup Classic. The winner of 19 Breeders’ Cup races and 171 Grade 1s, Brown takes a conscious moment to put his five-time $7 million-plus winner into context.
“You obviously hate to retire a horse that’s the best you’ve ever trained, and when they leave your stable you fear you’ll never get another horse as good as this,” Brown said. “As a trainer you have to think about that carefully. You hope that another Sierra Leone will join us, but there is certainly no guarantee of that.
“He’s certainly a very rare horse, that’s the bitter part of this,” Brown continued. “The great thing is that he will go to the best breeding farm in the world and get a well-deserved, pampered retirement, where he will have every opportunity to excel in his second career and be cared for like a king – and he will go home safe. For a horse that means so much to you, to send him to the best possible home for a second chapter – that’s the great thing.”
Sierra Leone has been in the spotlight since selling for $2.3 million at Fasig-Tipton’s 2022 Saratoga Sale and has long been a welcome push for the country’s biggest trainer, with expectations undeniably high. Owned by Peter Brant, Mrs. John Magnier, Michael Tabor, Derrick Smith, Westerberg and Brook T. Smith, the blue-blooded bay has been favored seven times in 13 starts, including the Travers (G1) and Belmont (G1). Only twice has his odds been above 2-1 – his headline loss in the Kentucky Derby (G1) at 9-2 and his triumphant Classic last year at 6-1 – while he rewarded connections with a trio of Grade 1 players, including last year’s Blue Grass (G1) and this year’s Whitney (G1).
ICYMI: Sierra Leone out @DelMarRacing it seems like he’s done this before pic.twitter.com/OYhNrffMpR
— Breeders Cup (@BreedersCup) October 28, 2025
“He taught me a lot,” Brown explained. “As a trainer who has done it at a high level long enough in races like the Kentucky Derby and the Breeders’ Cups, you feel like you’re really prepared to handle any situation. Then you get a horse like him and you realize there’s still more to learn and experience. As we close out his career, I feel like I’ve learned a lot from him to use in the future. The Derby is such a tough race to win and I think I can I’ve learned a lot from managing a horse of his caliber and I think we’ve done a really good job, but there’s always little things that you can go back on and say, ‘man, I can use this little piece of information to improve in a few little areas’, of course.
“For a horse that has never been off the field and has been so sound and healthy while being managed under a microscope and under a lot of pressure, I feel a lot of gratitude and satisfaction for me and my team,” he continued. “I feel like we did a really good job and as good as anyone could have done with him. Some things in racing and in sport are unfortunately always left up to luck and circumstance and there are so many factors, especially with horses. All the intangible and human elements on the playing field, if you look at what we’ve done with Sierra Leone, I know we’ve done our best to put him in a position to perform every time. I think we’ve achieved that.”
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