Kentucky Derby contender profile: Winning Impression

Trainer Dallas Stewart is no stranger to saddling live longshots in the Kentucky Derby (G1). Golden Soul (2013) and Commanding Curve (2014) both finished second at high odds in the Run for the Roses, stunning bettors who believed they were overmatched.

On Sept. 5, Stewart will return to the Derby with another unheralded longshot.

Winning Impression has yet to win a stakes race, and his Brisnet Speed ratings are lower than those earned by his acclaimed rivals. But the Derby can be a strange race, and if the Churchill Downs main track comes up sloppy, you can bet Winning Impression will relish the conditions.

A son of Haskell (G1) winner Paynter, out of the Unbridled’s Song mare Unbridled Sonya, Winning Impression was bred by WinStar Farm, where Kentucky Derby winners Funny Cide and Super Saver were produced. Despite a classy pedigree, Winning Impression sold for just $17,000 as a yearling and for $77,000 as a 2-year-old, and Stewart took on training duties for the partnership of West Point Thoroughbreds and Pearl Racing.

Much like Commanding Curve, who required four starts to break his maiden, Winning Impression was slow to learn the ropes of racing. He finished fifth in his first two starts sprinting, and failed to challenge on either occasion, but thrived when he stretched out to 1 1/16 miles for his third run. Over a sloppy track at Fair Grounds, Winning Impression overcame a wide trip to pull away and score by 3 1/2 lengths.

The jump to allowance company produced mixed results. Winning Impression finished second and third in a pair of two-turn events at Fair Grounds, before he traveled for a 1 1/16-mile route at Oaklawn Park. Again over a sloppy track, Winning Impression rallied gamely to cross the wire in front by a length, but he was disqualified for causing interference down the homestretch.

Winning Impression was the beneficiary of a disqualification in his next start. In a division of the Arkansas Derby (G1), Winning Impression produced a mild late rally to finish fourth against tough competition. But when the winner was disqualified because of a positive post-race drug test, Winning Impression was elevated to third, which secured him 20 qualification points on the Road to the Kentucky Derby.

Winning Impression’s summer campaign has been less fruitful. He produced seventh-place efforts in the Indiana Derby (G3) and Ellis Park Derby, but those races were over dry tracks, and there’s no telling how Winning Impression might fare if he catches his preferred sloppy footing at Churchill Downs.

When Golden Soul rode a sloppy rail to a runner-up effort in the 2013 Derby, his 34-1 odds triggered huge payoffs for the exacta ($981.60), trifecta ($6,925.60), and superfecta ($57,084.00).

Winning Impression’s connections — and handicappers interested in backing him on Derby Day — will be watching the weather forecasts for the first Saturday in September.