Bolero Bay must overcome post 10 on Saturday when he seeks to win his third consecutive race in a competitive renewal of the $100,000 Not Surprising at Gulfstream Park. The 1 1/16-mile route for 3-year-olds on Tapeta is one of three stakes on an 11-race card that begins at 12:50 p.m. Eastern. It’s counterpart for fillies is the $100,000 Martha Washington. The card also features 3-year-olds and up sprinting on dirt in the $100,000 Big Drama. The Not Surprising cast includes Behold the King, winner of the Armed Forces on turf in November at Gulfstream, and Khon Han, runner-up in last year’s Proud Man on dirt at Gulfstream. Bolero Bay has wired fields at Gulfstream in his last two starts, taking the $100,000 English Channel on May 2 and an allowance route April 9. Bolero Bay’s natural speed should serve him well when he breaks from the widest post Saturday, under jockey Miguel Vasquez. “He has enough tactical speed that I think from out there it will allow him to do what he wants to do,” trainer Michael Yates said. “I think he’s quick enough he can be forwardly placed and, if necessary, drop over. If somebody on the inside really has their mind set on making the lead, I believe he can sit off of them a little bit early.” :: Access the most trusted data and information in horse racing! DRF Past Performances and Picks are available now. Bolero Bay is moving back to Tapeta, where he earned a career-high Beyer Speed Figure of 78 two starts back. He earned a Beyer of 77 winning the one-mile English Channel over the local turf in his last start. The turf course is temporarily closed. “I thought his last race was a really big race,” Yates said. “I would have loved to see the race come back on the grass again. But, according to the numbers, his best race is the Tapeta. But visually, I thought that the grass race was his best race. He gets the opportunity to breeze over the Tapeta, so he’s no stranger to it.” Bolero Bay is one of just three runners in the Not Surprising who are proven on a synthetic surface. The others are Knoty Knicks and Justin Smiles. Bolero Bay has come to hand this year for Mast Thoroughbreds. He’s a three-time winner in 2026, beginning with a seven-length maiden win in both his turf and two-turn debut in January. Bolero Bay has stepped up his game for a couple of different reasons, according to Yates. “I just think the maturity and stretching out – and getting him off the dirt onto a surface that he desires was the big thing,” Yates said. “He had worked well enough going into his early dirt races that we felt like he had plenty of ability and then he didn’t run up to his works on the dirt. When we moved him to the grass he was a different horse.” Bolero Bay is a son of Basin and a half-brother to multiple stakes winner G W’s Girl. “He’s training well, had a couple of nice breezes between races, and we’re looking forward to Saturday,” Yates said. Martha Washington The form Nyfive brings into the Martha Washington mirrors that of Bolero Bay, and just like him, she will be breaking from the widest post Saturday. Nyfive has has scored front-running wins in her last two starts for trainer David Fawkes, with one coming on turf and the other on Tapeta. She will start from post 8 in the Martha Washington. Others entered in the 1 1/16-mile race include Bayou Brigid, who is coming off a win at this distance on turf at Gulfstream; R Slew of Cash, who was stakes-placed on Tapeta last year in the Wait a While; and Haute Diva, winner of last year’s Cash Run on dirt at Gulfstream. Keith Asmussen has the mount on Haute Diva for trainer Patrick Biancone. Earlier this year, the filly ran in some of the Gulfstream preps for the Kentucky Oaks. Big Drama Concrete Glory ran one of the best races of his career at seven furlongs. He will be returning to that distance for the Big Drama. :: Subscribe to the DRF Post Time Email Newsletter: Get the news you need to play today's races!  The race has drawn others who have been effective at the distance, including Back Em Up, Pure Class, and Chrome Ghost. Concrete Glory finished fourth last out after setting the pace at six furlongs in the St. Matthews on April 30 at Churchill Downs. Last year, he won a pair of allowances at seven furlongs, one at Gulfstream Park and the other at Saratoga. For his effort at Saratoga, he earned a Beyer of 96. Concrete Glory has speed and the rail and figures to be prominent from the bell. Micah Husbands has the mount for Big Frank Stable and trainer Saffie Joseph Jr. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.