Sierra Leone Odds to win the 2024 Kentucky Derby with Picks and Predictions

by Joey House - 4/24/2024

Sometimes systems or trends involving horse racing don't focus on the winners, but rather on the horses that will not win. A fairly significant trend has been to fade whoever sits atop the leaderboard of the Kentucky Derby Prep Races. The last points leader to win the Derby was California Chrome in 2014. This year's leader, Sierra Leone, looks to change that trend.

Unfortunately, there is also another popular trend going against Sierra Leone as well. It has been 33 years since a horse has won both the Bluegrass Stakes and Kentucky Derby. This prep race used to churn out Derby winners, with six horses winning both from 1963 to 1972. The powerhouse Spectacular Bid won the double in 1979 and then the curse began, with only Strike the Gold providing a brief interruption in 1991.

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Breeding: Sierra Leone has a very strong lineage, as evidenced by his A++ Equineline breeding rating. He was sired by Gun Runner out of the Malibu Moon mare Heavenly Love in March of 2021. His sire, the legendary Gun Runner, was an extremely accomplished and successful thoroughbred who was recently elected to the National Museum of Racing and Hall of Fame, winning 12 and finishing ITM in 17 of his 19 races. He too was the Kentucky Derby Prep Race points leader in 2016 and finished 3rd in the 2016 edition of the "Run for the Roses". Gun Runner was a speed merchant and passed both his speed and winning tradition onto his progeny. Out of the 482 foals Gun Runner sired, 169 (35%) of them have gone on to win a race. A testimony to his greatness is his current stud fee, anywhere between $250,00 to $350,000. Sierra Leone's broodmare dam, the deceased Malibu Moon, also had a knack for producing winners, with 1217 out of 2826 (43%) and earnings of $119,919,635. Included in that lengthy list of winners is 2013 Kentucky Derby champ Orb.

Trainer: Sierra Leone's trainer is Chad Brown, who is ranked 5th in earnings in 2024, with $5,736,138. His horses have won 27% of the races they've entered, which is tops among trainers with 100 or more races this season. He has yet to visit the winner's circle in the Derby, however, going 0 for 7. His best finish was a second-place with Good Magic in 2018. who lost to the eventual Triple Crown winner Justify. Brown will also have Domestic Product entered in the Derby.

Jockey: After his second-place finish with Jose L. Ortiz aboard in the 2023 Remsen (G2), Brown decided to go with Tyler Gaffalione as Sierra Leone's jockey. He's currently in 4th place on the earnings list with $6,675,549 among jockeys who have raced 200 or more times. He is a prolific rider, with 478 rides under his belt so far this season, the third most in racing. While he has over 50 wins and over $25 million in graded-stakes races, his performances at the Kentucky Derby have been abysmal, going 0-for-6 and his highest finish of 7th in 2019 on War of Will.

Prior experience: Sierra Leone made his debut on November 4 in a maiden special weight over 1 mile at Aqueduct. After a rocky start, he pulled away and won with ease. His next race almost a calendar month later was what ESPN would call an "Instant Classic". On December 2, in the 2023 Remsen (G2), Sierra Leone trailed until the stretch run, where he made a furious bid to grab the lead from heavy favorite Dornoch. He did so briefly with a furlong left, but eventually succumbed to Dornoch by a nose at the wire. Sierra Leone started his 3-year-old season on a great note, winning the Risen Star Stakes (G2) in February. He once again came from the rear and one by a half-length on a sloppy track. A month and a half later, on April 6 at the Blue Grass Stakes (G1) at Keeneland, Sierra Leone was able to exact his revenge on Dornoch for his defeat in the 2023 Remsen. The start of this revenge race, however, was delayed almost two minutes as Sierra Leone vigorously fought going into the starting gate and was beginning to get close to being scratched. However, once loaded, he ran his normal race of saving ground and closing from the back. For a brief moment, he dueled with Dornoch in the stretch before pulling away from his rival and finishing in first place by one-and-a-half lengths.

Odds, Analysis, and Predictions: With these two wins and finishing atop the Kentucky Derby Prep Race Leaderboard, it's easy to see why Sierra Leone is the second favorite at 4-1. His pedigree is second to none and the abundant amount of speed that his sire Gun Runner possessed is evident in Sierra Leone's races. Handicappers like horses that have shown the ability to close, and that is Sierra Leone's forte. If there was ever a horse to buck all of the trends going against him, it would be Sierra Leone. What scares me the most is jockey Tyler Gaffalione's poor performance on the biggest stage. Having watched both of Gallalione's races on Sierra Leone, he has a great chance of checking off "Win Kentucky Derby" from his bucket list.

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