Ridden by Edgard Zayas, the 3-year-old Midshipman filly finished one length in front of the late-closing You Bought Her, who was 3 1/4 lengths ahead of the 3-5 favorite, Stonetastic, in the five-horse field of fillies and mares.
Dearest is trained by Gilberto Zerpa, who also ran longshot Danessa Again, who was expected to keep the front-running Stonetastic busy on the front end. But Danessa Again didn't break as fast as her stablemate did, and it was Dearest who put the early pressure on Stonetastic through an opening quarter-mile in :22.08.
After a half-mile in a zippy :44.34, those two were in a head-to-head battle, with Dearest racing to the outside of Stonetastic. At the top of the stretch, Dearest kicked into full gear.
"I had to change my plans a little bit," Zayas said. "I didn't think I was going to be on the lead going head-to-head. I thought someone else was going to go, but when I saw Stonetastic on the lead alone, I had to go catch her. I couldn't let her get away on her own, because she's a pretty tough filly to pass by. I watched the replays and every time she gets the lead she gets really tough to pass by. I had to go with her and see who had more horse at the end.
"I was really, really confident that (Dearest) was going to hold on. The last half-furlong I got a little bit worried, but she has a lot of class. She's a very nice filly."
The win was the fifth from seven starts for Dearest. Over the summer at Gulfstream, she won the Royal Palms and Azalea. In her last race before the Sugar Swirl, Dearest finished second in the Prioress (gr. II) at Saratoga Race Course in September.
"Instructions were at the break to put her behind (Stonetastic)," said Zerpa, who notched the first graded stakes win of his career with Dearst. "But Dearest had a really good break and was able to put herself in a great position. She is at her best right now and in optimal condition."
Dearest returned $5 to win as the second choice in the 35th running of the Sugar Swirl. She completed the distance in 1:09.59 over a track labeled fast. Daniel Burke and Kathleen Schweizer bred the chestnut filly in Kentucky out of the Cherokee Run mare Keowee Clai. She was a $150,000 buy from the 2015 Ocala Breeders' Sales Co.'s March sale of 2-year-olds in training when consigned by Woodford Thoroughbreds.