Skippylongstocking bids to become the first three-peat winner of the Charles Town Classic (G2) when the 6-year-old competes in the $1 million race the evening of Aug. 22.
Since the Charles Town Classic was inaugurated in 2009, four horses have become dual winners in back-to-back runnings of the 1 1/8-mile contest: Researcher (2009-10), Imperative (2014-15), Art Collector (2021-22), and Skippylongstocking (2023-24). Now, the latter has his opportunity to stand alone as the winningest horse in West Virginia's richest race.
"We knew we wanted to bring him back and go for a third win in the Classic," trainer Saffie Joseph Jr. said. "The chance to make history is cool."
Skippylongstocking battles graded stakes winners Banishing, Awesome Aaron, Alexander Helios, Komorebino Omoide, Trademark, and two others.
Skippylongstocking, a 6-year-old son of Exaggerator owned by Daniel Alonso, dominated the past two runnings. Going quickly to the lead in both contests, he rolled by five lengths in the 2023 running before a 5 3/4-length triumph in last year's race.
More speed in this year's eight-horse field may require different tactics for the versatile Skippylongstocking, who has captured graded stakes races from pressing and stalking positions. His last win came two starts ago in the May 26 Hollywood Gold Cup Stakes (G2) at Santa Anita Park, where he rallied from fourth, 2 1/2 lengths off the pace.
Subsequently facing some of this country's best in the Aug. 2 Whitney Stakes (G1) at Saratoga Race Course, he checked in seventh, 12 3/4 lengths behind victorious Sierra Leone. He raced far off a hotly contested fractions for the opening half-mile, launched an early, mid-race move when the pace slowed, then emptied out through the lane.
He is winless in 11 grade 1 races, though he has picked up four top-level placings by showing in the 2025 Pegasus World Cup Invitational (G1), the 2025 Stephen Foster Stakes (G1), the 2023 Breeders' Cup Dirt Mile (G1), and the 2022 Belmont Stakes (G1).
He is 11-3-7 in 33 starts overall with earnings of almost $3.7 million.
Jose Ortiz rides Skippylongstocking, as he did in guiding him to victory in the 2024 Charles Town Classic.
Skippylongstocking is one of two Charles Town Classic entrants for Joseph, who also runs Alexander Helios, winner of the Razorback Handicap (G3) in February at Oaklawn Park. Alexander Helios comes off a freshening after being eased in the Blame Stakes (G3) at Churchill Downs in late May.
Banishing, who trainer David Jacobson co-owns with Lawrence Roman, is a leading threat. Besides his last-out nose win in the July 20 Jeff Hall Memorial Stakes at Ellis Park, he also captured the Oaklawn Mile (G3) in March in Arkansas. He also placed in grade 1 company this spring when dead-heating for second in the May 3 Churchill Downs Stakes (G1) when he was edged by a head by Mindframe, one of the leading older horses in the country.
Banishing breaks from the rail, likely allowing jockey Tyler Gaffalione to forwardly place his mount with a relatively short run to the first of three turns over the bullring at Charles Town.
Most effective to date over middle distances, Banishing is winless in three starts at 1 1/8 miles. The best finish in three starts at the distance from the son of Ghostzapper was a runner-up finish in the April 19 Oaklawn Handicap (G3).
Post time for the Charles Town Classic, the 11th of 13 races on the card, is 10:25 p.m. ET.
Hollywood Casino At Charles Town Races, Friday, August 22, 2025, Race 11Entries: Charles Town Classic S. (G2)
PP Horse Jockey Wgt Trainer M/L 1 1Banishing (KY) Tyler Gaffalione 121 David Jacobson 7/2 2 2Awesome Aaron (KY) Javier Castellano 121 Norm W. Casse 10/1 3 3Alexander Helios (KY) Irad Ortiz, Jr. 121 Saffie A. Joseph, Jr. 12/1 4 4Skippylongstocking (KY) Jose L. Ortiz 121 Saffie A. Joseph, Jr. 7/5 5 5Komorebino Omoide (JPN) Ramon A. Vazquez 121 Robertino Diodoro 10/1 6 6Trademark (KY) Fernando De La Cruz 119 Victoria H. Oliver 20/1 7 7Willy D's (KY) Luis Saez 119 Michael J. Maker 3/1 8 8Gould's Gold (KY) Brian Joseph Hernandez, Jr. 119 Kenneth G. McPeek 12/1
