Most of the puzzle pieces that make up Keeneland's Jessamine Stakes (G2T) clearly come from September's Kentucky Downs meeting, but the race's key element may have spent the summer in New York.
The Kentucky Downs results provide only limited help in figuring out the answers to a Breeders' Cup Challenge Series race that offers a "win and you're in" ticket to the Breeders' Cup Juvenile Fillies Turf (G1T) Oct. 31 at Del Mar since all but one of the 12 2-year-old fillies in the main body of the Jessamine made their last start at Kentucky Downs, as did one of the two also-eligibles. And six of the 14 exit wins at the unique all-turf track.
And for all of that, the eye is drawn to Time to Dream, who arrives in the Bluegrass from Saratoga Race Course, where she not only won her first two starts but thoroughly dominated them. The Not This Time filly, trained by Todd Pletcher for Repole Stable, won by 2 1/4 lengths on debut July 25 going one mile on the grass and then improved on that by taking the P. G. Johnson Stakes a month later by 5 lengths.
"We were very excited about her debut and even more so coming out," Pletcher said after the second win. "She trained really well following her debut and she came over and handled herself very professionally."
"It's nice to have a filly like this one, a 2-year-old, and she's got that turn of foot," added jockey Irad Ortiz Jr, who will return for the Jessamine ride. "It's really special. As soon as she goes by the other horses, she started looking around, ears up ... very nice horse. Hopefully, we can keep going forward with her."
The issue for Ortiz and Time to Dream is the draw. She got the outside gate—never a plus but, in her case, maybe not a big minus as both her wins came from stalking trips and there's enough of a run to the first turn in the 1 1/16-mile race at Keeneland to establish a spot.
The morning line takes the optimistic view, installing Time to Dream as the 2-1 favorite.
The Kentucky Downs crowd is tougher to assess, both because form doesn't necessarily transfer directly from that undulating, kidney-shaped turf course to the flat Keeneland oval and because five of the aforementioned last-race wins came in maiden affairs.
Red Beretta, a Catalina Cruiser filly from the Michel Douaihy barn, exits a second-place finish in the Aug. 31 listed Kentucky Downs Juvenile Fillies Stakes, just a head behind Meringue in a wild finish. She was 75-1 in that heat while coming off a fourth-place showing in the Ellis Park Debutante Stakes.
Rose Room also returns from the Juvenile Fillies, where the photo found her fourth, just a neck back of Meringue. By Ghostzapper, the Michael Stidham trainee won her only other start by 2 lengths Aug. 7 at Delaware Park. The Godolphin homebred is cross-entered in the Oct. 4 Miss Grillo Stakes (G2T) at Aqueduct Racetrack.
Loveliest, the favorite in the Juvenile Fillies Stakes field, looks for a rebound from her seventh-place showing there. Eddie Kenneally trains the Siyouni miss.
Carolyncaroline was last seen finishing fourth, beaten 2 3/4 lengths, in the 6 1/2-furlong Untapable at Kentucky Downs after winning her first go easily on a sloppy Ellis Park track.
The Kentucky Downs maiden winners are Lit Ship, by Midshipman ; Mackinac, by Twirling Candy ; Aggressive Lime, by Authentic ; Diablo Shiraz, by Daredevil ; and Infinite Sky and Imaginationthelady, both by Not This Time.
Keeneland, Friday, October 3, 2025, Race 8Entries: Jessamine S. Presented by Keeneland Sales (G2T)
PP Horse Jockey Wgt Trainer M/L 1 1Lit Ship (KY) Jose L. Ortiz 118 Joe Sharp 6/1 2 2Mackinac (KY) Luis Saez 118 George R. Arnold II 9/2 3 3Carolyncaroline (KY) Julien R. Leparoux 118 Lindsay Schultz 15/1 4 4Aggressive Lime (KY) Flavien Prat 118 Brad H. Cox 8/1 5 5Rose Room (KY) Florent Geroux 118 Michael Stidham 20/1 6 6Victor Help Me (KY) Walter A. Rodriguez 118 Concepcion Torres 30/1 7 7Diablo Shiraz (KY) Sophie Doyle 118 John Ennis 50/1 8 8Loveliest (KY) Tyler Gaffalione 118 Eddie Kenneally 15/1 9 9Infinite Sky (KY) Luan Machado 118 Brad H. Cox 5/1 10 10Red Beretta (KY) Evin A. Roman 118 Michel Douaihy 20/1 11 11Imaginationthelady (KY) Lanfranco Dettori 118 Brendan P. Walsh 10/1 12 12Time to Dream (KY) Irad Ortiz, Jr. 120 Todd A. Pletcher 2/1 13 13Soloist (KY) John R. Velazquez 118 Kenneth G. McPeek 10/1 14 14Dyna (KY) Flavien Prat 118 Kevin Attard 6/1
