Casual Smile Upsets Matchmaker Stakes

William S. Farish’s Casual Smile, a 9-1 chance, closed with a bold move between horses to upset the Grade 3 Winstar Matchmaker Stakes for fillies and mares a by a length and a quarter under a brilliant ride by Abel Castellano Jr.

I’m Already Sexy, the even-money favorite in the field of eight, finished second, three-quarters of a length before Testa Rossi, the 5-2 second choice.

Casual Smile, a 4-year-old daughter of Sea the Stars trained by Chad Brown, stopped the timer in 1:47 flat for the mile and a sixteenth on firm turf. She paid $21.20, $6.80 and $3.40 across the board and topped a $68.80 exacta with I’m Already Sexy, who returned $3.20 and $2.20. Testa Rossi, also trained by Brown, paid $2.60 to show.

Casual Smile was still several lengths off the leaders in mid-stretch when Castellano asked for speed. The filly responded with a burst, zipping between horses to open daylight at the wire.

“I had a lot of confidence going into the stretch with a lot of horse left,” Castellano said. “I found a very small hole between horses to get through and had a lot of faith in my horse that she would get through.”

This was the first graded stakes victory for Casual Smile, and her third straight win since breaking her maiden at Monmouth on May 24.