The best longshot to bet in the 2023 Kentucky Derby

Thinking far outside the box paid off handsomely in the 2022 Kentucky Derby (G1), as Rich Strike delivered the biggest upset in the modern history of the race by returning $163.60 to win. So good was the payoff that merely playing $2 to win on the 10 longest shots on the board, all of whom were more than 20-1, would have resulted in a sizable profit.

That exercise might be a fun way for the inexperienced bettor or casual fan merely looking to get lucky to enjoy the Derby, but scooping out a nice longshot that looks semi-logical in advance just feels better in the end, right?

While relative inexperience and trouble caught up with my longshot suggestion in last year’s Derby, this time I’ll be looking to use a candidate with a few more miles under his belt and who’s coming out of a seemingly stronger prep.

One of the final horses to make the field after some defections last weekend, #9 Skinner (20-1) is rightfully in his proper place in the Kentucky Derby after finishing third in both the San Felipe (G2) and Santa Anita Derby (G1) in his last two starts.

Although produced by multiple Grade 3-winning sprinter Winding Way, whose full sister was multiple Grade 2-winning sprinter Kauai Katie, Skinner gets an injection of stamina via his sire Curlin, the two-time Horse of the Year and Hall of Famer who won or placed in all three Triple Crown races in 2007.

Skinner ran the best race of his career in the Santa Anita Derby, finishing only a half-length behind the winning Practical Move, who nosed out Japanese invader Mandarin Hero (a Derby also-eligible). Skinner was able to rate closer to the leaders than he had in the San Felipe, and the better positioning got him within hailing distance of the top pair at the finish.

Thought enough of to contest the Del Mar Futurity (G1) and American Pharoah (G1) as a maiden last season, Skinner finally put it all together in his 2023 season debut, graduating over one mile at Santa Anita by more than three lengths. His relative inexperience showed in the San Felipe, but the Santa Anita Derby was a clear step forward.

As for Skinner’s human connections, trainer John Shirreffs is known in Derby lore for saddling Giacomo to a 50-1 upset in 2005. Although Giacomo broke his maiden at an earlier stage than Skinner, their stakes records are similar. Giacomo was also Grade 1-placed at two and ran third, second, and fourth in his three Derby preps.

New to Skinner will be jockey Juan Hernandez, who replaces three-time Derby-winning jockey Victor Espinoza. That might not prove to be the wisest move from an experience standpoint, but perhaps that will help keep Skinner’s price higher. Hernandez is routinely one of the top riders on the Southern California circuit and owns a career win percentage of 21%.

Skinner remains far from the finished article, but should offer excellent value in the Kentucky Derby coming out of one of the fastest preps. He’s a must-use for me in the vertical exotics, if not for the win.