2024 Kentucky Derby Best Bets

From a wagering perspective at the top betting sites, this year’s Kentucky Derby has a different feel to it.

Only three horses have single-digit odds going into Saturday’s big race and just five horses have odds less than 20-1. Does that mean picking the winner or for win, place and show is less complicated? Unfortunately, not really.

Here is the dilemma each horse bettor has to determine. The two favorites, Fierceness and Sierra Leone drew two gate positions nobody wants. Fierceness drew #17 and that position has NEVER WON in 44 attempts. And, Sierra Leone drew the #2 slot and the last horse to win from that spot was 1977, which was Triple Crown winner Affirmed.

Now, here is the crazy part. If those two horses would have drawn each other’s positions, and despite the history, Fierceness is a noted frontrunner who could have charged to the lead early and Sierra Leone is a closer and could have been nicely spotted.

2024 Kentucky Derby Best Bet: #4 Catching Freedom to Win 8-1 at Bovada (visit our Bovada Review)

#4 Catching Freedom (8-1)

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How to Watch the 2024 Kentucky Derby

When: Saturday, May 4, 2024
Time: 02:30 PM ET
Where: Churchill Downs
How to Watch: NBC/Peacock

2024 Kentucky Derby Horses

2024 Kentucky Derby Info

Race: 12
Post Time: 6:45 PM ET
Race Status: Grade 1
Distance: 1 1/4 miles
Conditions: Dirt
Purse: $5,000,000
Track: Left-handed

True Derby Contenders

Besides coming out of the worst gate in Kentucky Derby history, Fierceness also brings an air of unpredictability about him. If he runs like he did in the Florida Derby and is near the front heading around the first turn, this race might be over. At the same time, he’s capable of a dud, which he’s done twice in five starts. If Fierceness is boxed in the home stretch, his interest might not be there.

Since going to blinkers, Sierra Leone has looked fantastic. He’s taken on others in this race like Catching Freedom, Just a Touch and Track Phantom waxing that trio. It will be important for jockey Tyler Gaffalione to get his ride into a comfortable spot and in the right lane so SL can make his closer move to win.

Who is the only horse to improve its Beyer Speed Ratings by five points in each start? Catching Freedom. He’s not had a bad race and veteran rider Flavien Prat should be able to carry out trainer Brad Cox’s game plan. Likely heavily bet on Saturday to win or for an exacta.

Arguably the best Japanese horse to enter the Run for the Roses is Forever Young. He’s shown the distance won’t be an issue and he has versatile tactical speed to pick his spots. Sharp horse bettors were hoping for higher odds as a value play.

Long Shot Contenders

Honor Marie looks the best of this bunch. HM already has a win at Churchill Downs and was an impressive 2nd at the Louisiana Derby. Trainer Whitman Beckwith has worked for both Hall of Fame trainers Todd Pletcher and Chad Brown and is nicely positioned in the #7 hole. If the track is fast on Saturday, watch out.

One always has to pay attention to the Santa Anita winner, because horses out west have performed well the last 15 years at Churchill on the first Saturday in May and Stronghold fits the bill. He has three wins and three runner-up finishes in six career starts, including a pair of stakes wins. Stronghold would likely have lower odds if not coming out of the #18 slot.

Mystik Dan and Encino are our other two long shots and both would need a super trip and have their A-Game. In horse racing, that is always possible and Mystik Dan won the Southwest Stakes, though on a sloppy track. He did come back with a solid 3rd at the Arkansas Derby. Encino took the Lexington Stakes and has three wins and a second in four starts. He's won out front or off the pace, however, this is a step up in class.

Kentucky Derby 2024 Best Bets

Win – #4 Catching Freedom
Place – #2 Sierra Leone
Show – #17 Fierceness
Exacta Box – #4, #3, #7