OCEANPORT, N.J. – Under a sweet ride by Abel Castellano Jr., Casual Smile rallied from second to last in the eight-horse Matchmaker Stakes to win going away by 1 1/4 lengths Sunday at Monmouth Park. Casual Smile, trained by Chad Brown, came into the Grade 3, $150,000 Matchmaker off a powerful victory over first-level allowance company. She made the jump to graded competition look easy as she advanced into the stretch, spilt horses nearing the furlong pole, and left the favored I'm Already Sexy and the second choice Testa Rossi in her wake. "I saw a little hole, I had a lot of horse, and she went right through," Castellano said. Casual Smile was bred by owner Will Farish, in Great Britain. She made her first five starts there in 2013 and 2014 but was unable to win. Now 4, it took her four starts this season before she won a maiden race at Monmouth in late May. She came back July 5 to win an allowance race handily, and she now has made the jump to graded stakes company. Casual Smile paid $21.20 to win as the fourth betting choice. She covered 1 1/8 miles over firm turf in 1:47.12. At the start, Means Well and Baffle Me set slow fractions of 24.49 seconds and 48.14. I'm Already Sexy and Testa Rossi moved up three and four wide on the far turn as the pace quickened through six furlongs in 1:11.57. I'm Already Sexy and Testa Rossi continued willingly in the stretch but could not quicken as Casual Smile went by them from the inside. I'm Already Sexy bested Testa Rossi for second by three-quarters of a length. The Matchmaker is sponsored by WinStar Farm, which donates stallion seasons to the top three finishers. Farish will have the choice of a free season to any of Paynter, Take Charge Indy, or Fed Biz. The first foals of Paynter and Take Charge Indy were born this year, while Fed Biz entered stud in 2015. The connections of I'm Already Sexy will get second choice of the remaining two stallions, and the owners of Testa Rossi will receive the remaining season. Castellano is having an excellent meet and came into the day third in the standings behind Paco Lopez and Trevor McCarthy after having finished sixth on the riders' list last year. He has won two stakes at the meet for Todd Pletcher, two for Theresa Pompay, and now one for Brown. "I have a lot of opportunities from the trainers, and I am trying to take advantage of it," he said.