Skippylongstocking lands Pegasus World Cup in fourth try

Skippylongstocking entered Saturday's $2,903,800 Pegasus World Cup (G1) having enjoyed a stellar career. Twelve wins in 35 career starts, numerous graded stakes victories — though none at the Grade 1 level — and more than $3.7 million in earnings.

These credentials did not cause most bettors to overlook some serious flaws. Among them were three previous losses in the World Cup, an 11-0-4-7 record at the top level, and only a workmanlike head score in the Dec. 20 Harlan's Holiday (G3) in his final World Cup prep.

Despite that record, the seven-year-old veteran ran the race of his life at Gulfstream Park on Saturday, closing from a ground-saving position in the second tier to upset the 1 1/8-mile fixture at odds of 21-1. His closest rival was stablemate White Abarrio, who had beaten Skippylongstocking by 6 1/2 lengths in the same race 12 months ago.

Aided by a strong pace set by 3-2 favorite Disco Time, who was making his first start outside Grade 3 company, Skippylongstocking closed fastest under Tyler Gaffalione to win the World Cup by 1 3/4 lengths. He covered one lap of Gulfstream's fast main track in 1:48.49 and paid $45.20.

"It's amazing. At seven years old, he was doing better than ever," said Saffie Joseph Jr., the trainer of Skippylongstocking and White Abarrio. "The Harlan's Holiday was a big race. It was either he was going to show up, or he was going to be retired. He showed up, but he did better since then."

White Abarrio, making his first start since Aug. 31, settled for second by 5 1/2 lengths over Full Serrano.

"I had all the confidence in him going into this race, but I was so focused on White Abarrio," Joseph added. "I wanted Abarrio to come back and run in this race. I'm so proud of White Abarrio. I can't believe how he ran for the preparation that he had, to come back the way he just did. I'm just proud of both horses and happy for both owners."

The order of finish was rounded out by Captain Cook, British Isles, Banishing, Lightning Tones, Disco Time, Mika, Poster, Brotha Keny, and 2025 Florida Derby (G1) winner Tappan Street, the only horse to have beaten reigning Horse of the Year Sovereignty last season.

Skippylongstocking added $1,686,000 to his lifetime bankroll with this initial Grade 1 win for owner Daniel Alonso. He has won four times at Grade 2 level: the 2023 and 2024 editions of the Charles Town Classic, the 2024 Oaklawn H., and the 2025 Hollywood Gold Cup.

His Grade 3 triumphs include two editions each of the Harlan's Holiday and Challenger at Tampa Bay Downs, as well as the West Virginia Derby. He was also classic-placed at three, finishing third to Mo Donegal in the 2022 Belmont (G1).

A Kentucky-bred, Skippylongstocking is by Exaggerator and out of Twinkling, a War Chant mare who has also produced the stakes winners Olivia Twist and Moonlite Strike.