Skippylongstocking Seeks Third Victory in $1 Million Charles Town Classic

The Exaggerator colt will attempt this Thursday to become the first three-time winner of the million-dollar event in West Virginia, facing Banishing, Alexander Helios, and other formidable rivals

Skippylongstocking, a true star / BENOIT PHOTO

WEST VIRGINIA, Estados Unidos (Special for Turf Diario).- Since its inception in 2009, the Charles Town Classic (G2) has established itself as the premier and richest race in this region of the United States, offering a $1 million purse over 1,800 meters. In its history, four horses have captured back-to-back editions, but none have achieved a three-peat—until this Friday, when Skippylongstocking will attempt to make history.

The Exaggerator colt, trained by Saffie Joseph Jr. and owned by Brushly Hill LLC, will look to defend his crown after dominating the two previous editions wire-to-wire. In 2023, he won by five lengths, and last year extended his advantage with an even more authoritative 5 3/4-length victory around Charles Town’s oval.

“We knew we wanted to bring him back to chase a third win. The chance to make history is something special,” said Joseph, confident his horse will arrive in peak condition.

The challenge will not be easy. Unlike previous editions, the presence of several speed horses could require a tactical adjustment. Skippylongstocking is versatile—he can take the lead, stalk, or close from off the pace, as he demonstrated in his penultimate start, the Hollywood Gold Cup Stakes (G2), where he finished fourth but surged powerfully late.

His most recent effort, however, left a bittersweet taste: he finished seventh in the demanding Whitney Stakes (G1) at Saratoga, nearly 13 lengths behind Sierra Leone (Gun Runner), after a trip that proved uncomfortable. Still, his overall campaign speaks for itself: 11 wins, nearly $3.7 million in earnings, and four Grade 1 placings, including the Pegasus World Cup Invitational 2025, Stephen Foster Stakes, Breeders’ Cup Dirt Mile, and the 2022 Belmont Stakes.

With José Ortiz aboard—who guided him to last year’s victory—Skippylongstocking enters as the horse to beat. But he won’t be alone. Among his chief rivals is Banishing (Ghostzapper), trained by David Jacobson, who comes off two major wins this year: the Oaklawn Mile (G3) and, most recently, the Jeff Hall Memorial Stakes (L), where he prevailed by a nose. He also dead-heated for second in the Churchill Downs Stakes (G1), just half a neck behind Mindframe (Constitution), one of today’s top runners.

Another threat is Alexander Helios (Cairo Prince), stablemate of the favorite, winner of the Razorback Handicap (G3) in February and returning from a brief layoff to rebound from a disappointing effort in the Blame Stakes (G3). Other notable contenders include Awesome Aaron (Practical Joke), Trademark (Upstart), and the Japanese import Komorebino Omoide (California Chrome), all with solid credentials.

The Charles Town Classic will be the 11th race on a 13-race card, scheduled for 10:25 p.m. ET. Skippylongstockinghas the chance—on his hooves, not hands—to etch his name in the history books as the first three-time winner of West Virginia’s richest race.