Sierra Leone

Sierra Leone was victorious in his career debut outing which came in a 2-year-old maiden race going one mile at Aqueduct on Nov. 4, 2023. That winning effort led to a graded stakes try in his second lifetime outing in the Grade 2, $250,000 Remsen Stakes going 1 1/8 miles at Aqueduct on Dec. 2. Sierra Leone made a big, menacing closing move in the Remsen to take a brief lead in deep stretch until settling for second by a nose when Dornoch was resurgent near the finish line, denying Sierra Leone the victory.

Sierra Leone returned for his 3-year-old debut in his next race on Feb. 17, 2024, in the $400,000 Grade 2 Risen Star Stakes going 1 1/8 miles at Fair Grounds, where he was sent off as the 2.70-1 favorite in a field of 12. Sierra Leone sat near the rear of the field much of the race under jockey Tyler Gaffalione and rallied from ninth to catch front running Track Phantom and win by a half a length on a sloppy, sealed racetrack. The Risen Star Stakes was a key prep race on the Road to the 2024 Kentucky Derby, and with his win, Sierra Leone earned 50 Derby qualifying points.

Trained Chad Brown Sierra Leone next sent Seirra Leone to the $1 million, Grade 1 Toyota Blue Grass Stakes April 6 at Keeneland. The Gun Runner colt was reluctant to load in the 1 1/8-mile race but once he settled in and the race was underway, he relaxed into a comfortable rhythm near the back of the 10-horse field. Sierra Leone launched a sweeping rally on the final turn and surged into contention in early stretch, lugging in a bit through the final furlong while reeling in runner-up Just a Touch for a convincing victory. With the win, Sierra Leone solidified his status as one of the top contenders for the Kentucky Derby May 4 at Churchill Downs.

Sierra Leone drew post position No. 2 in the Kentucky Derby, which last yielded a winner in the run for the roses in 1978. Sierra Leone dropped back near the rear of the field in the early running before launching a rally and was forced to go very wide into the stretch as he moved into position. He closed through the lane along with Forever Young, lugging in and leading on that rival throughout the final furlong, and ultimately came-up a nose short on the line and settled for second in a 20-horse field at Churchill Downs on May 4. 

Sierra Leone sat out the Preakness Stakes and made his next start in the Belmont Stakes back at the 1 1/4-mile distance on June 8 at Saratoga. Sierra Leone was sent off as the 1.70-1 favorite atop a 10-horse field in the Belmont Stakes but got off to a troubled start and ended up settling for a closing third-place finish, beaten a total of 1 1/2 lengths by his old nemesis Dornoch.

The colt returned for his fifth start of 2024 in the Jim Dandy Stakes Presented by Mohegan Sun July 27 at Saratoga, and as is his custom rallied strongly in the stretch to finish a length behind Fierceness in second. He next targeted the DraftKings Travers Stakes Aug. 24 at Saratoga and rallied for third behind familiar foe Fierceness and runner-up Thorpedo Anna.

Following that string of four in-the-money starts without a victory, Sierra Leone trained up to the Longines Breeders’ Cup Classic Nov. 2 at Del Mar and was somewhat overshadowed by Fierceness, Japan’s Forever Young, and Europe’s City of Troy among 3-year-old contenders. He settled in his usual position well off of what turned out to be a sizzling early pace in the 1 ¼-mile Classic and began to pick off horses in the far turn. lavien Prat kept Sierra Leone out of trouble and wide of the leaders at the quarter pole, and the colt swept to the lead in early stretch and powered clear to a career-defining, 1 ½-length win over Fierceness and Forever Young in the Classic.

Sierra Leone’s win in the Breeders’ Cup Classic helped him secure the Eclipse Award as champion 3-year-old male for 2024, and his connections were honored during the annual ceremony on Jan. 23, 2025.

Sierra Leone remained in training for his 4-year-old season in 2025 and made his seasonal debut in the Grade 2 $500,000 New Orleans Classic going 1 1/8 miles at Fair Grounds on March 22 and finished third in a five-horse field. He then finished second by a length behind Mindframe in his subsequent start in the Grade 1 Stephen Foster Stakes at Churchill Downs on June 28.

Sierra Leone's 4-year-old breakthrough finally came for him in his third start of the season, and he picked a big spot to do it in the Grade 1 $1 million Whitney Stakes going 1 1/8 mile at Saratoga on Aug. 2. Sent off as the 1.95-1 second choice in a loaded nine-horse field in a Whitney field that also included Fierceness, White Abarrio, and other heavy hitters like Skippylongstocking and Highland Falls, Sierra Leone patiently sat back in last behind a live pace under jockey Flavien Prat for the first half of the race. He made a strong move into contention on the turn and took over the lead in the stretch and drew off to a one-length victory.

Sierra Leone returned for his next start four weeks later in the Grade 1 $1 million Jockey Club Gold Cup at Saratoga where he settled for second by 1 1/2 lengths behind Antiquarian after being steadied back behind the field when negatively impacted by trouble after the start as rival Mindframe lost his rider. He then trained up to the Breeders’ Cup Classic, where the 4-year-old would again face Fierceness and Forever Young along with top 3-year-olds Journalism and Baeza along with his stablemate and dedicated pacesetter Contrary Thinking. Sierra Leone made his customary closing charge in the Classic but came up a half-length short to Forever Young. That marked his final career start before retiring to a stallion career.

Sierra Leone was bred in Kentucky out of Grade 1 winner Heavenly Love, by Malibu Moon. He sold for $2.3 million at auction as a yearling.