Kentucky Derby 2020 Radar: Chestertown easing onto the trail

Chestertown, the record $2 million colt purchased at last March’s Ocala Breeders Sale of 2-year-olds, is back to breezing for trainer Steve Asmussen in a new locale.

The son of Tapit, out of the Grade 1 winner Artemis Agrotera, ran to expectations at second asking Dec. 1 at Aqueduct, where he rallied to defeat fellow New York-breds in a one-mile maiden special weight event.

Now, the partnership of West Point Thoroughbreds, Mary and Chester Broman, Woodford Racing, Siena Farm and Robert Masiello are looking toward the 2020 Kentucky Derby trail. But they’re not in any great hurry.

With Chestertown having clocked in Monday with a five-furlong breeze at Louisiana’s Fair Grounds in 1:01.60, Terry Finley, president and CEO of West Point, said connections are looking to face winners in open company.

“And then hopefully we’ll be in a position where that performance in the allowance race will warrant taking a shot at bigger things,” Finley said.

The gray Chestertown graduated when stretched from 3/4 of a mile on debut to eight panels, scoring with relative ease as an even-money favorite. Afterward, Finely said, “We think he’s a legitimate horse,” and that’s why Chestertown’s moving away from the state-bred ranks.

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Offspring of Tapit are known for showing up for training as headstrong or immature mentally. That’s part of why Asmussen, who has conditioned, among others, the 2014 Kentucky Oaks and Breeders’ Cup Distaff heroine Untapable, received this assignment from the partnership.

“If Steve thinks something, he’ll tell you,” Finley said. “He’s very straightforward. I like the fact that he says he’s got as good as a mind as he’s seen on a Tapit. We hope he progresses, and we think he will.”

A look down Asmussen’s shed row reveals another reason the partnership selected the Hall of Famer to train Chestertown.

“It’s good that we’re in a position where Steve is able to gauge where he is at with his other good 3-year olds,” Finley said. “I know Steve likes him, so we’ll see. It’s very exciting.”

Asmussen is looking loaded with 3-year-old prospects after Silver Prospector won the Kentucky Jockey Club Stakes (G2) in November and Shoplifted rebounded to take the Springboard Mile in December. His other sophomore stakes winners include Hopeful Stakes (G1) hero Basin and Gold Street, who’s won back-to-back in the slop, most recently prevailing in Fair Grounds’ Sugar Bowl Stakes.

Asmussen has started 20 horses in the Derby during his career with runner-up finishes by Nehro (2011) and Lookin At Lee (2017) his best results thus far, while third-place runners Curlin (2007) and Gun Runner (2016) are more well-known for their accomplishments beyond the first Saturday in May.