Kentucky Derby Picks: Expert Win, Place Show Picks for Churchill Downs

Robert Criscola gives out his expert Kentucky Derby betting picks, and he's leaning on the top two finishers from the Blue Grass Stakes while paying respect to Florida Derby winner Fierceness.

Robert Criscola - Contributor at
Robert Criscola • Publishing Editor
May 4, 2024 • 17:05 ET • 4 min read
Blue Grass Stakes 2024 Kentucky Derby horse racing
Photo By - USA TODAY Sports

The 150th renewal of the Kentucky Derby takes place today at Churchill Downs, and 21 sensational sophomores have assembled for the historic event.

Fierceness and Sierra Leone are side-by-side in the Kentucky Derby odds, and both runners will factor into my free betting picks

Join me as I offer my 2024 Kentucky Derby picks and predictions for Saturday, May 4.

Kentucky Derby Predictions and Picks: Win, Place & Show

They say speed kills, and Fierceness is the fastest horse on paper heading into the Kentucky Derby.

Best Bet: Fierceness to win (+250 at FanDuel Racing)

Win Prediction: Fierceness (5-2)

No. 17 Fierceness stamped himself as an early Kentucky Derby favorite when he won the 2023 Breeders' Cup Juvenile. He took his time coming back, reappearing in the Grade III Holy Bull Stakes at Gulfstream Park, and settled for third after an awkward beginning. 

The son of City of Light quickly atoned for that with one of the most impressive displays by a three-year-old in years, crushing the competition in the Grade I Florida Derby and earning a 110 Beyer Speed Figure.

Fierceness is trained by Todd Pletcher, who's won this race twice and will be piloted by three-time Derby-winning rider John Velazquez. The tandem teamed up to score in 2017 with Always Dreaming.

Place Prediction: Sierra Leone (3-1)

No. 2 Sierra Leone is a nose away from being undefeated, and that lone loss was suffered in the Remsen Stakes at age two. He was narrowly beaten by Dornoch, who rode a gold rail in a gate-to-wire win while Sierra Leone took the overland route.

Of course, the son of Gun Runner could be forced wide or encounter traffic trouble in the Derby with his late-closing style, but he remains a logical choice to at least grab second on the "Run for the Roses."

Sierra Leone was an impressive winner in both the Grade II Risen Star Stakes and the Grade I Blue Grass Stakes in his two Kentucky Derby preps. Trainer Chad Brown and jockey Tyler Gaffalione are both in search of their first Derby wins, but this is as good a colt as both have been involved with on the first Saturday in May.

Show Prediction: Just a Touch (10-1)

No. 8 Just a Touch will try to pick up the Brad Cox barn following the scratch of Encino.

Though he has just one lifetime win going six furlongs, there are a lot of positives to take away from his runner-up results in both the Grade III Gotham Stakes and the Blue Grass. He went very wide on a muddy course at Aqueduct two-back but was cutting into the margin on eventual winner Deterministic at the wire, and he attended a fast pace before being collared by Sierra Leone at Keeneland.

Recent workouts are encouraging, and Florent Geroux retains the assignment.

More Kentucky Derby picks and predictions

Our experts are making Kentucky Derby picks and building bets all week.

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Where can I bet on the Kentucky Derby?

There are multiple legal horse racing betting sites that allow you to wager on the Kentucky Derby, but not every sportsbook can offer Derby odds. We have created a guide outlining the best Kentucky Derby betting sites available in your area.

Which states have legal betting on the Kentucky Derby?

Sports bettors can enjoy some form of online or retail wagering in 34 states (+ DC), but horse racing enthusiasts have even more legal options. Check out our list of legal states for betting on horse racing to see if wagering on horse racing is legal in your state via the FanDuel Racing app.

Canada (excluding Ontario)

Almost all sports betting sites offer fixed-odds wagering on horse racing. Discover the best sports betting sites in Canada, or sign up now with one of our top partners, bet365, and earn up to $200 in bet credits!


Following the changes to the iGaming regulations on April 4, 2022, horse racing betting is no longer available at sportsbooks. Those in Ontario who are looking to bet on the Kentucky Derby will need to sign up at one of Woodbine's two online offerings, HPIbet and Dark Horse Bets.

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