Handicapping the 2024 Kentucky Derby: How to turn $100 bet into a profitable venture

LOUISVILLE, Ky. — For most people betting on Saturday’s 150th Kentucky Derby, the excitement will merely be the opportunity to have a small rooting interest in the one horse race they’ll watch all year.

But for those who follow the sport regularly, this Derby as much as any in recent memory presents the fundamental question that every handicapper and horse player must ask themselves every year: Will the best horse be able to run his race? 

For the two colts who have stood out among this year’s 3-year old crop, that's an unusually complicated question. 

Fierceness, last year's 2-year old champion, has shown devastating speed and ability in his two big stakes victories, including a 13 1/2-length romp in the Florida Derby on March 30.

But he’s also proven that he’s capable of flopping: a well-beaten seventh in last fall’s Champagne Stakes and a tiring third in February’s Holy Bull, neither of which came with much of an excuse from trainer Todd Pletcher aside from a bit of jostling out of the starting gate. He’ll likely be the favorite in Saturday's race. 

The second choice is Sierra Leone, a physical standout who has carried high hopes from the moment he fetched $2.3 million at a yearling sale.

Sierra Leone, a Chad Brown trainee, has done nothing wrong in his four starts, losing just once by a nose last December to fellow Derby starter Dornoch. But Sierra Leone has shown just one running style in his career, settling well off the pace early before passing horses with one big late run. That means Sierra Leone will be at high risk of encountering traffic trouble as he navigates through the 20-horse field, especially coming out of the No. 2 post position where jockey Tyler Gaffalione will be under pressure to make quick decisions about whether to keep the horse on the rail or try to get a clearer running lane outside. 

If this were a typical 9-horse field on a Saturday at Santa Anita, it would probably be foolish to bet against those two. But this is the Kentucky Derby, where racing luck plays a massive role in the outcome, the ability to overcome adversity is magnified and — for the gambler — the financial upside of taking a stand against the favorites is enticing. 

In trying to identify a horse that will peak on Derby Day, I try to look for three factors:

• Which horse has already shown clear top-end ability but still has significant upside to improve?
• Which horse has a running style versatile enough to keep them out of trouble near the front while also staying just off the kind of hot early pace the Derby often produces?
• Which horse has some intangibles in their favor, whether that’s the human connections or breeding well-suited to this race? 

One entry in Saturday’s race checks all three boxes, and that's why I’m going to pick Just a Touch, who started the week as a 10-1 shot on the morning line. 

Purchased as a 2-year old for $300,000, Just a Touch didn’t make his debut until Jan. 27 this year at the Fair Grounds in New Orleans, winning by four lengths while posting a Beyer Speed Figure of 89 − a number that immediately suggested he was one of the fastest 3-year olds in training. 

From there, trainer Brad Cox took him to New York, where he ran a solid second in the one-turn Gotham Mile on a very sloppy track. Just a Touch then took yet another step forward on April 6 in the Blue Grass Stakes, sitting just off the pacesetters early and taking the lead at the head of the stretch only to be passed late by Sierra Leone.

All things considered, it was a strong showing in his first effort around two-turns. And given the breeding — he’s a son of 2018 Triple Crown winner Justify with perennial leading sire Tapit on his dam’s side — he projects to handle the 1 1/4-mile distance without a problem. 

Given all those factors, plus Just a Touch’s impressive morning gallops this week, I expect experienced jockey Florent Geroux to settle him in sixth or seventh place early behind a group of pacesetters that will include long shots Dornoch, Track Phantom and Stronghold with Fierceness jockeying for position right behind them. 

As the pretenders begin to fade on the far turn, we should get a sense of which Fierceness decides to show up. If he runs back to his Florida Derby, he’ll undoubtedly emerge at this point and be difficult to catch. But in that race, he was able to grab the lead quickly despite a slow opening quarter-mile of 24.16. At that moment, against a pretty soft field, the race was already over. In the Kentucky Derby, Fierceness is unlikely to get such a favorable setup and will be tested in a way he never has before. 

How will he react with Just a Touch breathing down his neck around the far turn and the closers — led by Sierra Leone and another Cox horse, Catching Freedom, beginning to roll from the back of the pack? 

If he handles it well, he probably wins. If he doesn’t, Just a Touch should be able to get the jump on everybody at the quarter-pole. From there, we’ll see just how much of a step forward he's taken since the Blue Grass a month ago. 

Among the others who could be involved late: Honor Marie, who won Churchill’s biggest 2-year old race last fall; unbeaten Japanese entrant Forever Young; and Mystik Dan, who posted an eye-popping 101 Beyer figure in winning Oaklawn Park’s Southwest Stakes on a muddy track. With the weather forecast for Saturday calling for occasional rain showers, it would be wise to include Mystik Dan and perhaps Dornoch in all exotic wagers due to their proclivity for an off-track. 

As usual, I’ll put my money where my mouth is and share how I plan on divvying up a $100 bankroll for the race:

≻ $25 to win on Just a Touch

≻ $5 exactas with Just a Touch over Catching Freedom, Honor Marie, Mystik Dan, Dornoch, Fierceness and Sierra Leone. ($30 total)

≻ $3 exactas with Catching Freedom, Honor Marie, Mystik Dan, Dornoch, Fierceness and Sierra Leone over Just a Touch. ($18 total)

≻ $1 trifecta Just a Touch with Catching Freedom, Honor Marie, Mystik Dan, Dornoch, Fierceness and Sierra Leone in the second spot and third spot. ($30 total)

That puts us $3 over budget, but hopefully it won’t matter come Saturday night if Just a Touch comes through as the key horse in all of these wagers. Good luck to those of you betting the 150th Kentucky Derby, and make sure to do so responsibly.