Gun Runner, one of the nation’s leading sires, swept the Kentucky Oaks exacta on Friday night at Churchill Downs, with daughters Always a Runner and Meaning finishing one-two. Gun Runner, the 2017 Horse of the Year and a first-ballot Hall of Famer, stands at Three Chimneys Farm, which co-campaigned him with Winchell Thoroughbreds. Three Chimneys bred Always a Runner and co-owns her with Douglas Scharbauer. The filly remained unbeaten in three career starts with her Oaks win, having previously taken the Grade 3 Gazelle Stakes at Aqueduct. Meaning came into the Oaks off her win in the Grade 2 Santa Anita Oaks. The fillies are among the 61 career stakes winners to date for Gun Runner, who was North America’s leading freshman sire of 2021. He quickly made the leap into the nation’s leading general sires, finishing among the top three by earnings in 2023, 2024, and 2025. Gun Runners’ progeny are led by 2024 Breeders’ Cup Classic winner and Eclipse Award champion Sierra Leone, Eclipse Award champion juvenile fillies Echo Zulu and Super Corredora, 2022 Preakness Stakes winner Early Voting, and Grade 1 winners Brant, Cyberknife, Further Ado, Gunite, Gun Pilot, Locked, Society, Taiba, and Vahva. :: Access the most trusted data and information in horse racing! DRF Past Performances and Picks are available now. Always a Runner is trained by Chad Brown, who conditioned Sierra Leone and Early Voting. Brown also trains Grade 2 winner Paladin, an early Kentucky Derby favorite who hopes to return later after being sidelined by injury. “As far as Gun Runner goes, obviously, one of the best sires in the world,” Brown said. “I’ve had plenty of them, fortunately, in my care. And I’d say that the class and the athleticism of these horses, they can come in all shapes and sizes, but I’ve never seen one that’s not an excellent mover. And I think that great stallions, when they throw that and they’re all efficient, excellent movers – like you look at this filly, you can watch this replay. Look at the mechanics of this horse. And that stallion, that’s what he consistently throws all the time. It’s remarkable.” ◗ Taylor Made Farm’s Not This Time, one of the nation’s leading sires, was represented during Kentucky Derby week by four graded stakes winners that showcased his versatility. His Breeders’ Cup Juvenile Turf Sprint winner Cy Fair won the Grade 3 Mamzelle Stakes on Thursday. Later, two of his progeny went two turns on the turf for major victories, as Rhetorical won the Grade 1 Old Forester Turf Classic on Saturday and Imaginationthelady won the Grade 2 Edgewood Stakes on Friday. Not This Time also got a win at one turn on the dirt, with On Time Girl winning the Grade 2 Eight Belles Stakes on Friday. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.