When the Phipps family decided to sell all their yearling colts at the 2019 Keeneland September auction, it wasn’t because they were intending to leave the business they had been involved in for nearly a century. The decision to sell came three years after Ogden Mills “Dinny” Phipps had passed and his children Daisy Phipps-Pulito and Ogden Phipps were certainly planning to keep the stable going. “This was just one of the ways we can sort of spread our risk a little bit,” Phipps-Pulito said. The reward for spreading the risk has turned into a Kentucky Derby starter for the Phippses, their first since Orb won the roses for them and Stuart Janney III in 2013. The Phippses, along with partners Mike Repole and Vinnie and Theresa Viola, will be represented in Saturday’s 147th Kentucky Derby by Dynamic One, a son of Union Rags whom Repole and Viola bought for $725,000 from the Phipps consignment. Even before the auction, Todd Pletcher, who trains for Repole and Viola, asked Phipps-Pulito that if they bought him would the Phippses like to stay in. :: DRF's Kenucky Derby Headquarters: Contenders, latest news, past performances, analysis, and more “I said, ‘Absolutely, we would love to,’ and it’s been a lot of fun since then,” she said. “He’s a really nice horse out of a good family. We always thought he was a horse that is bred for those classic distances and that was a really solid number we got for him.” Out of that yearling sale – in which the Phippses sold six colts for a total of $2.14 million – the Phippses also partnered with Viola and Repole on a Curlin colt, Distinction, a $200,000 purchase, who has already been retired, and with Peter Brant on Tour of Duty, a son of War Front who sold for $700,000 and who is 0 for 1 with trainer Chad Brown. Phipps-Pulito said that her family has been close friends with the Violas for several years. Phipps-Pulito said Vinnie Viola is someone from whom she frequently seeks advice. “He’s been one of those guys since my dad’s passed away that if I have a question about the business or other business stuff I’ll call him,” Phipps-Pulito said. “I love his opinion on things. I think he’s an honest guy. He gives me really good information. There’s no baloney, and I really appreciate that.” Viola, who in 2017 won the Kentucky Derby with Always Dreaming, said he’s admired what the Phipps family has meant to Thoroughbred racing. “When I came back into the sport in 2011-12, one of the things I committed to do was study the matriarchal bloodlines,” said Viola, who added he hired noted bloodstock expert John Sparkman to assist. “When I started to realize what the Phipps family had done with their broodmare band . . . what a generational history. The family has to be dedicated to these horses; it says a lot about the people involved in the sport from these families.” Dynamic One is out of the dam Beat the Dreams, who went winless in two starts. Deeper in the pedigree are champion mares Storm Flag Flying and Personal Ensign. Phipps-Pulito said she has never met Repole but has communicated with him via an email and text chain that involves multiple members from all three families. “It’s just been super fun,” Phipps-Pulito said. When Repole first got involved in racing he owned all the horses he raced by himself. A few years ago, he began partnering with others and in 2019 won the Breeders’ Cup Classic with Vino Rosso, a horse he owned with Viola. “I’ve owned a lot of horses by myself but owning horses with Vinnie and having horses like Vino Rosso and winning big races together, it’s like an extended family, you really get to meet great people,” Repole said. “It really is fun.” Lately, it has become more fun to own Dynamic One. After three straight losses to begin his career, Dynamic One took a 1 1/8-mile maiden race at Aqueduct by 5 1/4 lengths on March 7. A month later, he was in front in deep stretch of the Grade 2 Wood Memorial only to be run down in the last jump by Bourbonic, a 72-1 shot, also trained by Pletcher. Those two efforts, and Dynamic One’s subsequent training, have his connections feeling quietly confident heading into the Derby in which jockey Jose Ortiz will wear the Phipps’s iconic black silks and cherry cap. “This horse has a big race in him. I don’t know when it’s going to be, but he’s training really well, he’s constantly moving forward, and that’s the way you’d want a horse going into a race like the Derby,” Phipps-Pulito said. “While I know we’re probably not in the top five or seven horses, I think we might be a sleeper in this race.” Dynamic One is the second crop of horses that Phipps-Pulito bred with Walker and Seth Hancock of Claiborne Farm after the passing of her father. “Nobody wants to be a failure in their family, and I sure as hell had a lot to live up to,” she said. Phipps-Piluto isn’t sure if the family will sell its yearlings this coming fall or instead sell some broodmares. “We’ve been a little more aggressive selling stuff that doesn’t fit into our program,” she said. “But we still have 20 to 25 mares and dad had that many at the end of his life. I don’t care what the number is, I want to make sure they’re the right horses.”