Grade 1 winner and track-record breaker Skippylongstocking, who has amassed over $6 million in earnings and claimed twelve graded stakes victories alongside ten triple-digit Beyer speed ratings, will retire in 2027 to stand at Amsterdam Two Farm in Middleburgh, New York, following the end of his racing career.
This son of Exaggerator, out of the four-time black-type producing War Chant mare Twinkling, will enter stud duty at a fee of $3,500, with the possibility of an increase after November 1 depending on his performance in the upcoming Breeders’ Cup Classic at Keeneland.
Skippylongstocking’s most notable triumph came in the 2026 $3 million Grade 1 Pegasus World Cup Invitational Stakes at Gulfstream Park, where he delivered a powerful late surge to win by 1 3/4 lengths against a strong 12-horse field that featured other Grade 1 winners such as White Abarrio and Tappan Street.
His entire 12 stakes wins have been on dirt surfaces facing graded rivals, including back-to-back victories in the G2 Charles Town Classic, the G2 Oaklawn Handicap featuring a career-best 107 Beyer figure, the G2 Hollywood Gold Cup, and three successive editions of the G3 Michelob Ultra Challenger Stakes—once in track-record time of 1:41.2 for 1 1/16 miles at Tampa Bay Downs. Among his graded stakes placings, he finished third in the 2022 Belmont Stakes and the 2023 Breeders’ Cup Dirt Mile, competing against top horses like Cody’s Wish and National Treasure.
Owned throughout his career by Daniel Alonso, Skippylongstocking showed early promise by winning his maiden race by an impressive 10½ lengths as a two-year-old at Gulfstream Park.
Ken Williams, manager of Amsterdam Two, praised Skippylongstocking’s physical presence, stating, “At nearly 17 hands, he’s about as imposing a stallion prospect as you can find. In a market that prizes size and scope, breeders are going to be thrilled to see this massive stallion in person.”
Amsterdam Two will present Skippylongstocking to the public on Sunday, October 11, from 4:30 to 5:00 p.m. near Saratoga’s Oklahoma Training Track, across from the Fasig-Tipton Saratoga Fall Mixed sale grounds.
Plans are set for Skippylongstocking to finish his racing career with the Breeders’ Cup Classic at Keeneland before making a repeat attempt in the Pegasus World Cup next January. He will compete under the partnership of Alonso and Joe Tesiero’s Amsterdam Two Stables.
Alonso, retaining a significant ownership share, reflected on the journey: “Skippy has brought my family and me an incredible adventure. From Florida to California, Arkansas to West Virginia, he has won on six different surfaces at distances ranging from one mile to one and a quarter miles. With Belmont Park’s recent upgrades and the increased incentives for New York-breds, launching his stud career here is a natural choice.”
Trainer Saffie Joseph, Jr. chimed in, praising Skippylongstocking’s remarkable consistency at the highest level: “Thirty-two consecutive starts against graded stakes competition is nearly unheard of in North America’s handicap division. I’m already excited for 2030 when I get to train the first foals bearing his name.”
Marketing lead Michael Slezak highlighted the strong pedigree behind Skippylongstocking, noting Twinkling’s impressive record of producing multiple graded stakes winners on dirt, as well as a high-value juvenile by Not This Time. “Being sired by Exaggerator, a Preakness winner and son of Curlin, we expect Skippylongstocking to be part of a powerful new wave of Curlin lineage shaping the breed’s future alongside stars like Cody’s Wish and Elite Power,” Slezak explained.
Williams also mentioned that contracts for breeding seasons, shares, and lifetime breeding rights signed before November 1 would remain at current prices, but further success at the Breeders’ Cup could prompt fee adjustments.
The agreement to stand Skippylongstocking at Amsterdam Two was facilitated jointly by Slezak and Matt Bowling of Bowling Bloodstock.
This story first appeared in the Paulick Report’s News section on October 2, 2026.
Fan Take: This announcement is a thrilling moment for horse racing enthusiasts because Skippylongstocking brings both elite racing credentials and an exceptional pedigree to the breeding barn, promising to influence the sport’s future generations. His New York-based stud career could also energize regional racing circuits and breeding programs, showcasing how top-tier talent can help grow the industry nationwide.
Source: sports.yahoo.com
