To be honest, the numbers were not in favor of Chad Brown’s thoroughbred. 3 times Sierra Leone had raced at the Saratoga racecourse. “He’s been the favorite three times. He’s burned money three times,” racing analyst Matthew DeSantis said on X before the Whitney Stakes race on August 2. “Maybe the fourth time’s the charm.” Or maybe it was the added incentive of the Breeders’ Cup that did the trick.

The Gun Runner-sired colt has always had the hype about him. And he justified it when he clinched the Breeders’ Cup Classic in 2024. Now, the 4-year-old colt will be back to defend his crown at the Del Mar racecourse. But what a stylish way he booked his ticket! And impressive!

NYRA shared the news on X on August 3: “SIERRA LEONE wins the Grade 1 Whitney Stakes! Last year’s @BreedersCup Classic champ books his return with a “Win and You’re In” score under Flavien Prat for trainer Chad Brown!” They also shared the race video with the post. So much to unpack.

We already knew how significant this race was. Not only because the winner straight up qualifies for this year’s Breeders’ Cup Classic on November 1st. There’s also the lucrative prize purse on offer. The winner got $550,000, while the runner-up was awarded $200,000. The third-placed thoroughbred took home $100,000, making the total purse for the Whitney Stakes $1 million. These two factors were enough to bring in a competitive field.

And that makes Leone’s win all the more noteworthy. Running home the 1⅛ mile dirt race in 1:48.92, the Chad Brown trainee won the G1 race by a length ahead of Highland Falls. In third came Disarm, two lengths behind the Curlin-sired colt. Leone’s powerful surge as the race hit the mile length turned out to be masterfully executed by jockey Flavien Prat. DeSantis’ favorite, Fierceness, who led the race for a long while, disappeared behind Leone and Falls, finishing in fifth place.

A grand way to announce his return for the Breeders’ Cup, as the 2024 Blue Grass Stakes winner clinched his fifth win in 12 starts. And now, he has a remarkable shot at history.

Chad Brown’s Sierra Leone is looking at elusive double

The 2025 Breeders’ Cup Classic is already looking emphatic. Sierra Leone returns for the defense of his 2024 crown, which he won beating Fierceness and Forever Young. In fact, the win helped him clinch the American Champion Three-year-old Male Title. But winning it this time won’t be easy, especially when there are the two thoroughbreds who have dominated the Triple Crown races this year.

Sovereignty and Journalism are being favored at the Classic by analyst Jonathon Kinchen. “If Journalism and Sovereignty both grow up, wow, what a race we might be looking at … Sovereignty is not too far off from a figure standpoint. And I think at a mile and a quarter with a lot of pace to run at, he’s going to have an advantage on Sierra Leone because Sierra Leone comes from so far out of it.”

Del Mar also is a happy hunting ground for Bob Baffert. So, the odds are quite stacked against the 4-year-old defending champ. But the chance to rewrite history might entice the dirt-track specialist. Thoroughbred enthusiast Brian Zipse shared a teasing update on X: “I’m not saying it’s going to happen this year, but the last and only horse to repeat in the Breeders’ Cup Classic is … Tiznow!”

For 23 years, the record has been standing. The iconic Tiznow was the last to win back-to-back Breeders’ Cup Classics in 2000-2001. Even the legendary Triple Crown winners Justify and American Pharoah don’t hold that distinction. For Sierra Leone, the challenge is as hard as it gets. But never say never.