Chestertown Crowned Down Broadway Retired Racehorse of the Year

Local boy makes headlines and returns home to settle down. That’s a familiar plot in movies and television, and it’s also the case with Chestertown. Now six, the handsome New York-bred grey once again turned heads Friday as he headed into the winner’s circle to receive the Down Broadway Award as New York’s Retired Racehorse of the Year. The award is named for the first horse to retire through the TAKE THE LEAD Program back in 2013.The theme of the sixth annual New York Thoroughbred Aftercare Day was “A Salute to Racetrack Ponies,” and Chestertown has been learning the ropes of his new career, even if that wasn’t the original hope when the regally bred son of Tapit was born at the nearby farm of popular breeders Chester and Mary Broman. Produced by their standout racemare Artemis Agrotera, Chestertown was presented for sale as a 2-year-old by Becky Thomas’s Sequel Bloodstock and brought a then-record $2 million for a New York-bred at auction.

“I think he was supremely talented, and very, very smart,” Thomas reflected. “He was a very high-energy horse. Aftercare is near and dear to me—we still have Freud here at the farm—and it takes a lot of people willing to do the work and a lot of money to support that.”

Trained by Steve Asmussen for the partnership of West Point Thoroughbreds, the Bromans, Woodford Racing, Siena Farm, and Robert Masiello, Chestertown won five of 25 career starts and $428,045 as a racehorse. His career highlight came right here at Saratoga in 2020, when he triumphed in the Albany Stakes.

NYRA’s head outrider Miguel Gutierrez was ready to step in when it was determined that Chestertown’s racing days were over.

“When I’m looking for a horse to be an outrider’s pony, it’s important that he be a Thoroughbred, an ex-racehorse,” Gutierrez said. “I need to know a horse can be fast for at least a quarter-mile. That’s my priority.”

Chestertown has made steady progress for the experienced horseman and his team.