Sierra Leone Bids for Second Classic in Career Finale

When Sierra Leone crossed the wire first in the 2024 Breeders' Cup Classic (G1) at Del Mar, his ownership group of Peter Brant, Westerberg, Brook Smith, and the Coolmore-affiliated Susan Magnier, Michael Tabor, and Derrick Smith took time to ponder his future, specifically whether to race him in 2025 or have him become a stallion at Coolmore's Ashford Stud in Versailles, Ky. As a multiple grade 1 winner with an attractive pedigree and looks to match, a stallion career was the lower-risk, higher-reward financial option. But rather than collect those profits, his ownership group decided to continue racing the now 4-year-old son of Gun Runner, who in January was honored as the champion 3-year-old male of 2024. Four starts later, Sierra Leone has $998,200 in the bank in 2025 with the possibility of earning more if he can repeat in the $7 million Breeders' Cup Classic Nov. 1 at Del Mar. "I haven't got off that cloud that I've been floating on. None of us have," co-owner Brook Smith said. "It's his last race, which is bittersweet, but also amazing. I'm really glad he had the chance to race this year." While Sierra Leone can earn a racing payday of more than $3.6 million if he can win Saturday, that falls well short of the profits that can be made from a high-end stallion. A stud standing for $50,000 and covering 200 mares can generate $10 million in annual stallion revenue—a fee and book size Sierra Leone potentially could have surpassed. His owners bought him for his racing and stallion potential when spending $2.3 million to acquire him as a yearling in 2022 at Fasig-Tipton's The Saratoga Sale. Bred in Kentucky by Debby Oxley, Sierra Leone is out of the grade 1-winning Malibu Moon mare Heavenly Love. He is 5-5-3 in 13 starts with career earnings in excess of $7 million. He has four graded stakes wins and an additional eight graded placings. If Sierra Leone triumphs Saturday—joining Tiznow in 2000-01 as the only repeat winner in Classic history—he would very well command a higher fee at stud in 2026 than after a single Classic win. Coolmore indicated that his stud fee will be announced after the Breeders' Cup when he takes up residence at Ashford. "He has all the right credentials now for when he retires, but if he was to win the second Classic, it would be an incredible feat," said Coolmore representative M.V. Magnier. Through its affiliated owners, Coolmore has an ownership stake with partners in three Classic horses—Fierceness and Journalism being the others. Fierceness, like Sierra Leone, heads to stud at Ashford Stud next year. Journalism, a 3-year-old, will ultimately join the stallion lineup there, though a decision of whether he races in 2026 or goes to stud will not be made until after the Breeders' Cup. Trainer Chad Brown acknowledged that Sierra Leone's 2025 season got off "to a little bit of a slow start," when he missed the $20 million Saudi Cup (G1) in February in the Middle East, and returned with a third-place finish in the March 22 New Orleans Classic Stakes (G2) at Fair Grounds Race Course & Slots. "But once he got going and got that first race under his belt, and we took him north, I felt the horse really rounded back into form," Brown said. He called a runner-up finish to Mindframe in a slow-placed Stephen Foster Stakes (G1) at Churchill Downs "excellent"—the same word he used to describe a win in the Whitney Stakes (G1) at Saratoga Race Course from Sierra Leone and a troubled runner-up finish in the Jockey Club Gold Cup Stakes (G1) there under jockey Flavien Prat. Prat had to alter course in the opening furlong around a fallen jockey, Irad Ortiz Jr., after he was unseated from Mindframe in a chain reaction incident caused by scrambling for early positioning, principally from his pace-making stablemate Contrary Thinking and rival Phileas Fogg. Stewards disqualified the latter from third for interference, demoting him to seventh. "He was 18 lengths behind and Prat told me he nearly pulled him up on the first turn, and he only got beat a length and a half. So he's put three really good races together. His sheet numbers are really good—right in line with his best numbers," Brown said. "I think he's got a chance at making history and joining that really rare list with Tiznow." As in the Whitney and Jockey Club Gold Cup, Contrary Thinking will join him in the Classic. Uncoupled with Sierra Leone in the wagering, Contrary Thinking is the only non-stakes winner in the Classic field and is certain to be the highest odds of any Classic starter. READ: Contrary Opinions Do Not Faze Brant, Brown on Pacemaker A pacemaker was not needed last year in a pace-laden lineup. Late-running Sierra Leone relished the conditions, launching a devastating second-turn rally to go from eighth to third from the 6-furlong to the mile marker, before passing his remaining two rivals in the final furlong of the 1 1/4-mile Classic. Early splits of :22.43, :44.96, and 1:09.44 fueled his rally, in which he hit the wire in a final time of 2:00.78. "He's coming into (the Classic) as good as last year," Brown said. "His last work was as good as I've seen from him. As you saw from his training, he's shining. He's a picture of health right now, which you love to see as a trainer before a big race." Derrick Smith, Brook Smith, Brant, and others associated with the ownership group watched Sierra Leone gallop Oct. 30 from atop a viewing stand on the Del Mar backstretch. "I've been training for nearly 18 years. I will tell you that you won't find a finer group of gentlemen and sportsmen to train for than this ownership group," Brown said. "Honestly, they've never interfered with how I train the horse, where I run the horse. "They brought this horse back, obviously with enormous value as a stallion. They could have just stood the horse last year, but they brought him back for everyone to see run with the goal of coming back to Del Mar to defend the title. I think it says a lot about how much they care about the industry, how much they care about their horses, and their big-picture view of horse racing globally. It's an honor to train for them."