2023 Kentucky Derby long shots: Why underdog horses continue to have success plus expert picks

Since 2000, only 10 post-time favorites have won the Kentucky Derby. Six came in a flurry of favorites between 2013 and 2018, almost certainly due to a change in the qualifying system for the race established by Churchill Downs.

Rich Strike won the 2022 Kentucky Derby as an 80-1 longshot. How does a horse that big of a longshot win America’s most famous horse race?

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Prior to 2013, horses gained entry by their earnings in graded stakes races. Beginning in 2013, horses had to earn qualifying points in a series of races designated by Churchill Downs, thereby virtually eliminating sprinters, horses running at mostly seven furlongs, and favoring horses who earned the most points running at longer distances.

This year, that points system was adjusted, offering more points in certain races and awarding points to horses that finished fifth in designated races; before this year, points were awarded only to horses finishing first through fourth.

But since 2018, no favorites have won, and three of the last four winners have gone off at double-digit odds: Rich Strike in 2022 at 80-1; Mandaloun in 2021 at 27-1 (following the disqualification of 12-1 Medina Spirit); and Country House in 2019 at 65-1 (following the disqualification of 9-2 Maximum Security.

The Kentucky Derby demands that a group of three-year-old horses do many things they’ve never done before. None of the entrants have ever run a mile and a quarter. None have raced in front of 120,000 people. None have raced in a 20-horse field. Less than half the field has run at Churchill Downs.

The unknowns and the variables may well add up to chaos on Saturday, and if you’re looking to try to cash big, you might consider these factors and these horses.

Let’s look at Saturday’s long shots and which ones may be good picks. I’m considering only horses at 10-1 or higher on the morning line for our purposes.

Pedigree

Hit Show (30-1), Confidence Game (20-1), Kingsbarns (12-1), Skinner (20-1), Sun Thunder (50-1), Rocket Can (30-1), and Lord Miles (30-1) are all sired by horses with a proven ability to throw runners with stamina. The sire of Lord Miles and Skinner, Curlin has gotten two Belmont Stakes winners and a Breeders’ Cup Classic winner.

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Uncle Mo, the sire of Kingsbarns, counts 2016 Kentucky Derby winner Nyquist among his progeny, while Into Mischief has sired two Kentucky Derby winners (Mandaloun and Authentic) and is represented by Rocket Can in this year’s race.

Horses for courses?

Eight of the 20 horses in the starting gate have already run at Churchill Downs. Three of them—Two Phil’s (12-1), Confidence Game, and Rocket Can–have won there. Confidence Game has four Churchill races on his record, two of them wins.

None of the horses have run at Churchill in at least six months, and a lot can happen as a horse progresses from his two-year-old season to the first Saturday in May. Some of those longshots from years past, like Giacomo, Country House, and Mine That Bird, had never raced in Louisville before their Derby start. But if you’re looking for a longshot angle, you might give these horses a look.

Mudders

Rain is expected in Louisville on Friday, and it had been forecast for Saturday as well, though it now looks like the Derby crowd will be spared a wet event. Still: keep an eye on the sky; if the track comes up wet, you can turn your attention to horses with a demonstrated affinity for the mud.

Eleven Derby runners have experience on off-tracks; seven have won, and five fall into our longshot category.

Confidence Game, who also has pedigree and Churchill experience, won his most recent start, the Grade 2 Rebel Stakes at Oaklawn Park in February, over a sloppy track. Rocket Can, similarly positioned as Confidence Game, broke his maiden in the mud at Churchill Downs after losing his first two starts over a fast track.

Raise Cain (50-1) romped by 7 1/2 lengths over an off track at Aqueduct Racetrack in Ozone Park, NY in the Grade 3 Gotham Stakes in March, and Japanese-bred Continuar (50-1) won his first race over a muddy Hanshin course in Takarazuka, Hyogo.

Two Phil’s won the Grade 3 Street Sense Stakes by 5 1/4 lengths at Churchill Downs on a sloppy surface.

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Handicapping longshots

Ken Rudulph is an on-air betting analyst and racing handicapper at FanDuel/TVG, and he cashed win tickets on both Giacomo ($102.60 for a $2 bet) and Country House ($132.40).

In 2005, when Giacomo won, Rudulph was at the beginning of his handicapping career, and he relied heavily on pedigree. As a two-year-old, the gray Giacomo had caught his eye with a flashy closing move in the Hollywood Futurity to finish second.

“Here comes this little gray streak, closing like a freight train,” recalled Rudulph. “And I thought, ‘I just found my Derby horse.’”

Giacomo was a son of Holy Bull, a Hall of Fame runner with demonstrated stamina, and while he arrived at the Kentucky Derby with just one win on his résumé, he had consistently finished in the top-three. And Rudulph had faith.

“It was so rewarding,” he said. “It taught me to trust pedigree connections and trust myself. It’s not going to work out every time, but that year, Giacomo made complete sense to me.”

Country House was quite another story. Reviewing the field for this year’s Derby, no horses stood out to him, so Rudulph focused on the humans rather than the horses.

“I love [jockey] Flavien Prat and I love [trainer] Bill Mott,” he said. “I said, ‘All right, let’s go with the 70-1 shot.’ I bet $50 to win and bet him in exactas, and then he gets put up after Maximum Security got disqualified. It was crazy fluke luck.”

And then there’s my friend who loves birds, who bet $2 across the board (win-place-show) on Mine That Bird, cashing tickets worth $183 off a $6 bet.

This year, I’m intrigued by Confidence Game. He’s got pedigree, and he’s got a win over the course. If the rains do come, I’m going to throw a couple of dollars on Two Phil’s, too.

(Photo of Confidence Game: Andy Lyons/Getty Images)

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