After 35 starts, 12 victories and nearly $3.8 million in earnings, Skippylongstocking has long since earned his place among the most reliable campaigners of recent seasons. Yet as the Pegasus World Cup 2026 approaches, Daniel Alonso’s 7-year-old gelding heads back to Gulfstream Park still chasing one final prize that has narrowly eluded him — a Grade 1 triumph on racing’s biggest stages.
Consistency has been Skippylongstocking’s hallmark. Ten of his 12 wins have come in graded company, and his durability has carried him coast to coast, through classic races and elite older-horse contests alike. For Alonso, the journey has been as meaningful as the results.
“We’d love to get him a Grade 1,” Alonso said. “He’s taken us so many places where we never thought we’d ever go and made us so proud. That would really mean something.”
That opportunity comes again on Saturday when Skippylongstocking lines up in the $3 million Pegasus World Cup (G1), becoming the first horse in the race’s decade-long history to compete for a fourth time. In doing so, he breaks a tie with Seeking the Soul and War Story, underscoring both his longevity and his connections’ faith in him.
Few horses show up as dependably at the top level. Despite a demanding career, Skippylongstocking has remained remarkably sound, something Alonso credits above all else.
“He shows up every time,” he said. “We thank God he’s never been injured. He’s been a picture of consistency and health.”
His Pegasus record reflects both the highs and lows of elite competition. Seventh behind Life Is Good in 2023, he endured a difficult 2024 renewal after being pressed hard from the outside and tiring on the far turn. Importantly, he walked off unhurt and returned just five weeks later to win the Challenger (G3) at Tampa Bay Downs, one of three consecutive victories that reaffirmed his resilience.
Those setbacks remain something of a mystery to his owner.
“We have no idea why those races didn’t go his way,” Alonso said. “He came back good, ate well, and wasn’t sore, so we kept going.”
Last year’s Pegasus saw Skippylongstocking finish a close third, just a neck behind multiple Grade 1 winner Locked, as White Abarrio dominated in record time. Both horses return for the Pegasus World Cup 2026, though this time they will be separated in the gate. Skippylongstocking, who previously endured wide draws, landed a favorable Post 5, while White Abarrio breaks from Post 11.
Trainer Saffie Joseph Jr. believes the draw could make a difference.
“Skippy is a hard-trying horse,” Joseph said. “He’s drawn better this year, and he’s doing well. He goes over there with a very good chance.”
The post-position announcement brought a rare moment of celebration even before the race itself, with audible cheers from the Alonso family — particularly Daniel’s father, Amancio, whose decades in the sport had never yielded a graded win until Skippylongstocking came along.
Purchased for just $37,000 after modest early sales results, Skippylongstocking has since delivered four Grade 2 victories, six Grade 3 wins and multiple Grade 1 placings, including Gulfstream’s Harlan’s Holiday in both 2022 and 2025.
“We were just hoping to have fun,” Alonso reflected. “Instead, it’s been an amazing ride for our whole family.”
As a 3-year-old, the gelding tested himself on the Triple Crown trail, finishing third in the Wood Memorial, fifth in the Preakness and third in the Belmont. Now, with 27 consecutive graded starts and appearances at 15 racetracks across nine states, he continues to compete at the sport’s highest level.
An official retirement plan has not been set, and Alonso prefers to let the horse guide the decision.
“He’s sound, healthy and happy,” he said. “We’ll go race by race and see where he tells us to go next.”
Whether or not the Pegasus World Cup 2026 finally delivers that elusive Grade 1, Skippylongstocking’s legacy is already secure — built on durability, heart and a journey that has brought an entire family along for the ride.
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