Punters will find a challenge sorting out an evenly talented group of juvenile turf runners in the $400,000 Bourbon Stakes (G2T) being run Oct. 4 at Keeneland.
Contested at 1 1/16 miles, the Bourbon Stakes is a Breeders' Cup Challenge Series: Win and You're In race for the $1 million Breeders' Cup Juvenile Turf (G1T) to be run at a mile at Keeneland Oct. 30.
Among the top contenders are three closely matched in the morning line, including Hemingway (5-2), Agate (4-1), and Bold Leadership (7-2).
Hemingway is son of Constitution out of the turf stakes-placed Quality Road mare Havana Dream. The colt comes into the Bourbon off a front-running 8 1/4-length romp in a 1-mile maiden special weight at Kentucky Downs, which was his second start and earned him recognition as a BloodHorse Maiden Watch Hot Prospect. He made his debut at 6 1/2 furlongs on the dirt at Saratoga Race Course and finished eighth. Hemingway races for WinStar Farm (which stands Constitution), First Go Racing, and CHC and is trained by Brad Cox. The colt will be ridden by Flavien Prat, who was aboard for his maiden win.
Dede McGehee's homebred Agate, a son of 2014 Breeders' Cup Mile (G1T) winner Karakontie , has made three starts on the grass. The gelding went unplaced in his debut and then followed with a 4 1/2-length win going a mile on the turf at Ellis Park. He most recently ran third in the listed Juvenile Mile Stakes at Kentucky Downs for trainer Kelsey Danner. He will be ridden in the Bourbon by Tyler Gaffalione.
Repole Stable and St Elias Stables' Bold Leadership is not a winner yet, but he's been oh, so close twice. The son of leading sire Not This Time ran second by a nose in his debut going 1 1/16 miles on the turf at Saratoga and followed with a second by a neck at the same distance in the With Anticipation Stakes (G3T). He is the only graded-placed runner in the field. Summer Wind Equine bred Bold Leadership out of the unraced Candy Ride mare Sweetened, who is a full sister to grade 2 winner Confidence Game and a half sister to grade 3-placed turf runner The Process. Todd Pletcher trains Bold Leadership and trained last year's winner of the Bourbon Stakes, Final Score, a son of Not This Time raced by Repole. The colt will be ridden by Irad Ortiz Jr.
Other Bourbon contenders coming into the stakes off a wins include Robert LaPenta's homebred Popcorn, a son of Catholic Boy , who is undefeated in two starts and last out won the Kitten's Joy Stakes on the turf at Colonial Downs by 2 lengths; Mark Arnold's Mad Mo, a son of freshman sire Mo Donegal , who captured his first win last out by 6 1/2 lengths going a mile on the turf at Horseshoe Indianapolis; and, Doubledown Stables' Mid American, a son of Epicenter , who last out won the listed Juvenile Sprint Stakes going 6 1/2 furlongs at Kentucky Downs.
Ruiva Favored In Indian Summer
Also on the Oct. 4 Keeneland card is the $350,000 Indian Summer Stakes (G3T), a 5 1/2-furlong turf sprint that has attracted a field of nine juveniles.
Three Chimneys Farm's homebred Ruiva is the 7-5 morning-line favorite, having run third in the Queen Mary Stakes (G2) during Royal Ascot and most recently second by a neck in the Sorrento Stakes (G3T) on the main track at Del Mar. Ruiva is a daughter of Munnings and one of five fillies in the field. She is trained by Wesley Ward and will be ridden by Ortiz.
The morning-line second choice is Smart Choice Stable's Wood Island, who is undefeated in two starts and comes into the race off a 2 3/4-length win in the Skidmore Stakes at the same distance on the turf at Saratoga. Wood Island is a son of top three freshman sire Jackie's Warrior .
Keeneland, Sunday, October 4, 2026, Race 10Entries: Castle & Key Bourbon S. (G2T)
PP Horse Jockey Wgt Trainer M/L 1 1Trim Castle (KY) Danny Sheehy 118 John Ennis 30/1 2 2Agate (KY) Tyler Gaffalione 118 Kelsey Danner 4/1 3 3Bold Leadership (KY) Irad Ortiz, Jr. 118 Todd A. Pletcher 7/2 4 4Heracles (FL) Luis Saez 118 Ronald B. Spatz 15/1 5 5Real Goodbar (KY) Jose L. Ortiz 118 Kenneth G. McPeek 10/1 6 6Popcorn (KY) Axel Concepcion 120 Jonathan Thomas 6/1 7 7Mad Mo (KY) Alex Achard 118 John Ennis 20/1 8 8Hemingway (KY) Flavien Prat 118 Brad H. Cox 5/2 9 9Blaring Ambition (KY) John R. Velazquez 118 Michael J. Maker 15/1 10 10Let Em Know (KY) Jareth Loveberry 118 D. Whitworth Beckman 20/1 11 11Mid American (KY) Jaime A. Torres 120 James P. DiVito 10/1
Keeneland, Sunday, October 4, 2026, Race 8Entries: Indian Summer S. Presented by Keeneland Select (G3T)
PP Horse Jockey Wgt Trainer M/L 1 1Adonius (IRE) John R. Velazquez 118 Rebecca Menzies 8/1 2 2Fanshell Beach (KY) Jose L. Ortiz 117 Wesley A. Ward 9/2 3 3Cactus Closer (KY) Junior Alvarado 118 Dale L. Romans 15/1 4 4Crack On (KY) Danny Sheehy 115 Jimmy Corrigan 12/1 5 5Love a Warrior (KY) Luis Saez 118 Steven M. Asmussen 8/1 6 6Ciarlatano (KY) Christopher A. Emigh 119 Brittany A. Vanden Berg 20/1 7 7Wood Island (KY) Flavien Prat 120 George Weaver 7/2 8 8Ruiva (KY) Irad Ortiz, Jr. 115 Wesley A. Ward 7/5 9 9Bee Crazy (KY) Tyler Gaffalione 115 Kelsey Danner 20/1
