Sierra Leone, the dark bay colt whose sire is Gun Runner, has really made a name for himself as one of the toughest racehorses around these days. Bred in Kentucky by Debby Oxley, he was bought for $2.3 million at the 2022 Saratoga Sale. He really showed his potential with a strong debut win at Aqueduct in November 2023. He kicked off his career with an exciting nose defeat in the Grade 2 Remsen Stakes, hinting at the dramatic photo finishes that would come to define his legacy.

With trainer Chad Brown at the helm, Sierra Leone really came into her own as a fierce closer, known for delivering some serious late kicks in big races. At just four years old, Sierra Leone is really making waves, especially with that amazing last-to-first win in the 2025 Whitney Stakes at Saratoga. Trainer Chad Brown even said it was a career highlight for him! Many doubts about the colt arose, nevertheless, due to the abundance of difficulties encountered earlier in the season.

Sierra Leone’s difficult start to the 2025 season

As we look into the 2025 season, Sierra Leone made an appearance in the Grade 2 New Orleans Classic, but the colt ended up finishing in third place. So, when he raced at Churchill Downs in the Grade 1 Stephen Foster Stakes, he ended up finishing second behind Mindframe. It was a close one, but the doubts started to rise about the 2024 Breeders’ Cup Classic champion. Is he really the same horse that used to win races?

Just before Sierra Leone arrived at Saratoga Race Course for the Grade 1 Whitney Stakes, a lot of analysts, including Matthew DeSantis, had pretty much taken the colt out of the winning conversation. “Second in the Derby, third in the Belmont, second in the Jim Dandy, third in the Travers. He’s run at Saratoga three times. He’s lost three times. He’s been the favorite three times. He’s burned money three times. Maybe the fourth time’s the charm. Maybe, but at 2-1 with a horse that is trip- and distance-dependent and pace-dependent, I’d rather not take that chance,” the analyst said before the Whitney Stakes, even though Sierra Leone was sitting at 2-1 odds.

The racing analyst mentioned that Sierra Leone is definitely impressive, but he has some specific needs: he requires a strong early pace to follow and a smooth journey—which can be tricky on a big race day since pace predictions and post positions can shift quite a lot. DeSantis’ thoughtful strategy really clicked with smart bettors who pay attention to the details rather than just going by reputation.

If Sierra Leone can’t find a clear way forward or if things pick up at the front, he might have a tough time making a strong late push. But the results of the Whitney Stakes really caught a lot of people’s attention, showing what Sierra Leone is capable of, even at just four years old.

The victory that changed the season for the horse

Sierra Leone, the current Breeders’ Cup Classic champion, really showed off some incredible closing speed to take home the Grade 1 $1 million Whitney Stakes at Saratoga on August 2. In an exciting last-to-first move, the 4-year-old Gun Runner colt zoomed past his rivals in the final furlong, beating Highland Falls by a length and making up for previous disappointments at Saratoga. He finally snagged his first win at the historic track after trying three times before, with close calls in the 2024 Belmont Stakes (3rd), Jim Dandy (2nd), and Travers (3rd).

This victory really put to rest any doubts about how he handles Saratoga’s surface. Fierceness, the 6-5 favorite, took the lead as they approached the stretch, but Sierra Leone made an impressive move, launching a strong rally wide and circling out to surge ahead of the competition, finishing in 1:48.92 for 1 1/8 miles.

Trainer Chad Brown shared his thoughts on the horse’s adaptability, saying, “I was happy with his position. He was quite far back and I knew when those horses were stopping out in the center of the track, that he was going to have to go inside horses and catch a lot of dirt. What we know about the horse now is that he’s a long, outside-run horse, like he did in the Breeders’ Cup and in the [2024 Kentucky] Derby and nearly won, so for him to cut the corner and catch a lot of dirt, which isn’t his preferred way to pass horses, making up considerable ground to then get out with blinkers full of mud and get there was a really remarkable run by him. A lot of heart.”

The Whitney was a Breeders’ Cup Challenge “Win and You’re In” race, which means Sierra Leone has earned a spot in the Classic at Del Mar on November 1, where he’ll be looking to defend his title. This win really helped him stand out among the top horses this season. So, TRCommentary on X states that Sierra Leone is just behind the three-year-old star Sovereignty, with Journalism coming in at sixth place.

That Whitney Stakes win really brought the colt back to the forefront of the industry, didn’t it? Sierra Leone has really made a name for himself as America’s top older horse, racking up $6.8 million in earnings and showcasing that impressive late-kick move. We’ll just have to wait and see if he can defend his Breeders’ Cup Classic title this time when everyone heads to Del Mar. But you know, this Whitney Stakes win was quite the emotional roller coaster for Sierra Leone’s trainer.

This win meant a lot for the trainer

Trainer Chad Brown, from Mechanicville, New York, has really made a name for himself at The Spa, scoring wins in almost every major stakes race—except for the Whitney. This win was a huge moment for him, being his first victory in the Whitney right in his own backyard, and it all came down to having the perfect horse for the task. For Brown, this race meant way more than just snagging another big trophy or getting a ticket to Del Mar.

The trainer of Sierra Leone opened up about what the victory meant to him, saying, “Growing up around here, the Whitney and Travers are what the whole meet has been built around since its early days, so, for me to finally get one of them with my mom and dad here, my brother, my two daughters, it’s memories that last forever… This is a really, really hard race to win, and you have to have the right horse.”

Brown has picked up five Eclipse Awards and has a great history at the Breeders’ Cup. However, winning a Whitney Stakes in his hometown has made professional recognition feel really personal for him. Brown grew up in Mechanicville, just a short drive from Saratoga, and would spend his weekends hanging out at the picnic area with his parents at the Spa. He really soaked up all the excitement of Whitney and Travers Day, even before he fully understood what horses were all about.

In that moment, right under the grandstand where he used to watch as a wide-eyed kid, Brown pulled off a win with a horse like Sierra Leone that might just outshine any title on his resume. It’s all about the personal connection he has with the racecourse. So, what’s up next for the racehorse and his connections?

Many more challenges are waiting for the colt

After his thrilling win in the Whitney Stakes, Sierra Leone is ready to dive into the next exciting phase of his impressive career. It looks like Chad Brown’s star colt has a pretty straightforward path ahead, with two big goals taking center stage for the second half of his 2025 season. First up is the exciting Grade 1 Jockey Club Gold Cup at Saratoga on August 31, a $1 million showdown that might include some of his toughest rivals.

Even though his come-from-behind style really worked wonders in the Whitney, Brown might prefer to have his horse a bit closer to the pace in this 1 1/4-mile race. A solid performance here would really lift Sierra Leone’s spirits and give some great ideas on how to tackle his main aim: defending his Breeders’ Cup Classic title. This time, the defending champion is probably going to face a tougher and more diverse group of competitors, with potential challengers coming from European stars to promising three-year-olds eager to shine.

The Classic is more than just another race for Sierra Leone; it’s a chance to really cement his legacy as one of the great closers we’ve seen in a while. Looking past these immediate goals, there are still some questions about what the future holds for Sierra Leone.

With more than $6.8 million in earnings and his value as a stallion prospect growing with each win, the team has to think about whether to keep racing him past 2025 or to retire him for breeding. Right now, all eyes are on the track, where this amazing athlete keeps showing the heart and determination that truly set him apart. Whether it’s charging down the stretch at Saratoga or powering home at Del Mar, Sierra Leone’s next moves are sure to grab the attention of racing fans and add another exciting chapter to an already remarkable career.