Who is the most intriguing Kentucky Derby longshot?

April 21st, 2021

With up to 20 horses in the Kentucky Derby (G1), a longshot often finds the frame. Last year it was Mr. Big News, who got up for third. Two years ago, Country House took the roses at longer odds than any horse but Donerail.

Let's get to know some of the most interesting dark-horse candidates for the greatest two minutes in sports.

We're looking at some real surprises — horses who haven't won a stakes yet. Then, have your say. Who is the most intriguing Kentucky Derby longshot?

Dream Shake

Dream Shake won a maiden special weight event at Santa Anita in February, at odds of 20-1, as convincingly as many thought the 3-5 favorite, Bezos, would.

He hasn't won in two starts since, but he nabbed third in both the San Felipe (G3) and the Santa Anita Derby (G1).

His running style is still evolving. He broke his maiden from well off the pace, though raced in closer range in both of his stakes efforts. That versatility will help in the Kentucky Derby.

Versatility defines his pedigree, too. Sire Twirling Candy has produced nice horses at many distances, including Santa Anita H. (G1) winner Gift Box and Queen's Plate victor One Bad Boy.

Twirling Candy is out of a Street Cry half-sibling to turf route stalwart Synchrony. Their dam, Brownie Points, was a stakes winner at middle distances on dirt and turf.

Dynamic One

A maiden winner at Aqueduct, Dynamic One looked well on his way to a win in the Wood Memorial (G2) for Todd Pletcher — until his stablemate, 72-1 shot Bourbonic, came to spoil the party.

Dynamic One got the jump on his stablemate, and that tactical speed could put him in a better place on Derby Day.

He also has plenty of pedigree for the stretch out to 1 1/4 miles. Dynamic One is by Belmont S. (G1) winner Union Rags and from one of the classiest female families in the stud book. Bred and co-owned by Phipps Stable, Dynamic One's second dam is Storm Flag Flying, and his third dam is My Flag, which makes him related to Miner's Mark, Parading, With Flying Colors, and Revved Up.

Hidden Stash

Though he finished third in the Sam F. Davis (G3), Hidden Stash made a better impression in the Tampa Bay Derby (G2), when he came in second, less than a length behind Helium.

He rallied for fourth in the Blue Grass (G2), a race where the same three horses were first, second, and third, in some order, all the way around.

Though Hidden Stash will need some pace help to win the Kentucky Derby, horses like him often run on to invade the exotics.

Pedigree helps his case. He is by Constitution (sire of last year's Derby runner-up Tiz the Law), out of the Smart Strike mare Making Mark Money. You'll find route class on both turf and dirt looking up Making Mark Money's family tree. Making Mark Money's second dam is La Affirmed, dam of Della Francesca, Caress, and Bernstein.

O Besos

He entered the Fair Grounds meet a one-start maiden, but after late-running wins in maiden and allowance sprints, O Besos joined the Louisiana spur of the Derby trail.

He ran on for fourth, behind the big three, in the Risen Star (G2), but outran two of them in the Louisiana Derby (G2), when he closed from last to get third, behind winner Hot Rod Charlie, and only missed Midnight Bourbon by a head.

It was a nice thing to see, at 1 3/16 miles, from a horse who had only won a one-turn race.

Looking at his pedigree, he is by Kentucky Derby winner Orb, out of the hard-knocking Soto mare Snuggs and Kisses, whose 12 wins were on turf and dirt, from seven to nine furlongs. Her three other foals have been sprinters or milers, with the most accomplished being sprinter Transatlantic Kiss.

Soup and Sandwich

This Mark Casse trainee hadn't faced stakes company before he took his shot in the Florida Derby (G1), but he proved he belonged in Gulfstream Park's premier Derby prep.

Forward early, Soup and Sandwich kept on going. He couldn't hold Known Agenda at bay but still finished well clear of the rest of his pursuers.

He is by supersire Into Mischief, who finally got his first classic winner with Authentic in last year's Derby. His dam, Souper Scoop, is by Tapit, the sire of three Belmont winners. Though Souper Scoop only climbed up to allowance company, she is out of Indiana Oaks (G3) winner Scoop (who also has graded quality form, like Coolwind and Looking Cool, underneath her). Scoop's dam, Til Forbid, is a Temperence Hill mare who finished second in the Alabama (G1).

Let us know your longshot to watch!