SARATOGA SPRINGS, N.Y. – Chestertown, a $2 million yearling purchase in 2019, broke through for his first stakes win Friday, holding off favored City Man to win the $150,000 Albany Stakes, the featured event on Saratoga’s 12-race New York Showcase Day program. Chestertown, a son of Tapit, won for the first time since he captured a maiden race at Aqueduct last December. He had gone winless in five starts as a 3-year-old, including double-digit-length defeats in the Grade 2 Louisiana Derby and Grade 3 Peter Pan. Friday, Chestertown raced in fourth position early with jockey Jose Ortiz liking his position outside of City Man, who, under Joel Rosario, went from the outside post to the rail around the first turn. Those two were tracking More Graytful, who was setting the pace stalked by Sky of Hook going a half-mile in 48.45 seconds and six furlongs in 1:12.17. Ortiz had Chestertown in second by the five-sixteenths pole, and Rosario had moved City Man to the outside for the stretch drive. City Man, a path or two outside of Chestertown, was on level terms in midstretch, but Chestertown held him at bay to the wire. Chestertown covered the 1 1/8 miles in 1:49.37 and returned $6.10 as the second choice. “At the three-eighths pole he really wanted to go by himself, but I didn’t want to let him run because I had Rosario inside of me and the guy in front of me I know I got him,” Ortiz said. “It took him a little while to get going, but when he felt [City Man] outside of him he regrouped and made another run.” The connections of Chestertown hope the Albany is a launching point to bigger things in the future. :: Play Saratoga with DRF! Visit our Saratoga shop for DRF PPs, Picks, Betting Strategies, and Clocker Reports Tom Bellhouse, chief operating officer of West Point Thoroughbreds – which is part-owner of Chestertown – said Scott Blasi, the assistant to trainer Steve Asmussen, told Ortiz in the paddock “no horse was training better in the barn and he was hoping he’d show up today and he did. Hopefully, it’ll lead us upward and onward eventually in open company as a 4- and 5-year-old.” Englehart: Three wins, but a big loss A roller-coaster of a day for trainer Jeremiah Englehart included three wins – two of which were stakes – but one major loss as Samborella, who won the $150,000 Seeking the Ante Stakes to begin the card, had to be euthanized after fracturing a sesamoid in her left foreleg. “Like my dad said, ‘You’re going to get punched in the gut a lot, it’s how many times you can get up,’ ” said Englehart, the son of trainer Chris Englehart. “I just feel bad for everyone that had a chance to work with her because she was special. The owners trusted me to take care of her, and it just sucks. But I have other horses that are depending on us, so we got to come back and leg another rider up.” Englehart did just that saddling Makingcents to victory in the $150,000 Fleet Indian Stakes for older females before ending the card some 6 1/2 hours after it began with a victory by Smite in a maiden claimer. In the Fleet Indian, for older females, Makingcents went to the lead under Luis Saez and held on for a neck victory over Ice Princess. Breaking from the rail, Makingcents came out a little on Ice Princess, who came in, at the start. Saez quickly corrected her and hustled Makingcents to the lead. She took some mild pressure from Courageous Girl before putting that one away nearing the head of the lane. :: DRF's Saratoga headquarters – Stakes schedule, previews, recaps, past performances, and more In the stretch, Ice Princess rallied along the rail while Sharp Starr, who leapt at the break, was rallying down the center of the track. Makingcents dug in to hold off both, beating Ice Princess by a neck with Sharp Starr another half-length back in third. “I wasn’t sure what a couple of horses were going to do, I told Luis let’s warm her up good, we’ll ask her her away and just play the break,” Englehart said. “If she goes out and you’re comfortable that’s fine. If not, at some point try to get to the front because she’s game when she’s on the lead.” Makingcents, a daughter of Goldencents owned by Richard Nicolai’s Fortune Farm, covered the 1 1/8 miles in 1:50.31 and returned $8.80. Englehart also sent out the favorite, Critical Eye, who faded to sixth and may have found the distance too far. In the Seeking the Ante, for New York-bred juvenile fillies, Samborella, also ridden by Saez, led gate to wire, but took a bad step as she crossed the finish line. She was vanned off, but the injuries were too severe. Samborella, a daughter of Outwork, was owned by a partnership that includes Gold Square, All About the Girls Stable, Paul Braverman, Fortune Farm, and Harlow Stables. She was a $500,000 yearling purchase at the Saratoga auction last year. Samborella covered 6 1/2 furlongs in 1:16.45 and returned $7.90 as the third choice. Make Mischief finished second, by nine lengths over Infringement. Rossa Veloce, Summer Brew, and Queen Arella completed the field. Rinaldi wires West Point Last fall, Rinaldi suffered a severe puncture wound in a foot that could have ended his life. But doctors at nearby Rood and Riddle Equine Hospital were able to treat the injury so it didn’t get infected. In the third start since his return, Rinaldi went gate to wire under Saez to win the $150,000 West Point Stakes by 1 1/2 lengths over Dot Matrix. It was three-quarters of a length back to Therapist in third. “We’re just so fortunate to be here today,” trainer James Bond said. :: Get DRF's Betting Strategies for Saratoga's weekend cards The win was the fourth from seven starts for Rinaldi, a 4-year-old gelding by Posse owned by Bond and friends Craig Allen and John and Amy Pickett, who are Bond’s neighbors. The win was the 12th from 38 starters at the meet for Bond. Rinaldi has been responsible for two of those wins. Rinaldi covered the 1 1/16 miles over good turf in 1:43.52. He was the third of what would become four wins on the card for Saez. Myhartblongstodady wires Yaddo Myhartblongstodady took advantage of the scratch of favored Fifty Five as well as a lack of pace to record a one-length, gate-to-wire victory in the $150,000 Yaddo Stakes. Wegetsdamunnys finished second, three-quarters of a length over Classic Lady. War Canoe and Kressie completed the order of finish. Myhartblongstodady, formerly trained by Chad Brown, was making her second start for Jorge Abreu, a former assistant to Brown. She won her previous start, in gate-to-wire fashion as well. Jose Lezcano was aboard Myhartblongstodady, a 5-year-old daughter of Scat Daddy owned and bred by Lawrence Goichman. She covered the 1 1/16 miles in 1:44.16 and returned $5 as the favorite. Brown said that Fifty Five suffered an injury that will likely lead to her retirement. The 6-year-old mare, a two-time champion New York-bred, won 12 of 23 starts – including nine stakes and banked $1,088,288. She began her career in the barn of Tom Bush for owners Empire Equines, before being bought privately early in her 3-year-old season by Peter Brant and transferred to Brown. Thin White Duke scores in Funny Cide The maiden Thin White Duke stormed down the center of the Saratoga main track to run by Lookin for Trouble and outfinish Eagle Orb to win the $150,000 Funny Cide Stakes for 2-year-old New York-breds. Eagle Orb finished second by one length over Lookin for Trouble. Thin White Duke, a gelding by Dominus, won for the first time in five starts. He had twice finished third on dirt at Belmont and twice finished second on turf earlier this meet. Phil Gleaves, the trainer, part-owner, and breeder of Thin White Duke, said he wanted to go back to the dirt because the only stakes for New York-bred juveniles in the fall at Belmont and Finger Lakes are on dirt. “We needed to find out if he belonged with these types of horses,” Gleaves said. “We scratched out of a maiden race to purposely run in this race to see if he would stack up. We felt he would stack up and he showed it today.” After setting a strong early pace on the turf, Thin White Duke, per instructions from Gleaves, rallied from next-to-last under Rosario in the Funny Cide, named after the gelding who won the 2003 Kentucky Derby and Preakness. “In his first start we thought he’d be on the lead and he hit the gate coming out and that put him back to last but he closed, so we knew he could handle that kind of tactic,” Gleaves said. “This was by design. I told Joel in the paddock tap on the brakes leaving there, let the speed go and he’ll finish.” Thin White Duke, whose ownership includes former Daily Racing Form CEO Steve Crist, covered the 6 1/2 furlongs in 1:16.75 and returned $12.20 as the fifth choice in the field of seven.