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Oaklawn Park

Skippylongstocking has come long way from yearling purchase to legend

Mary Rampellini|Mar 22, 2026
Skippylongstocking.Gaffalione,Tyler.1-24-26.BL_.jpg
Barbara D. Livingston Skippylongstocking won the Pegasus World Cup in January.

Skippylongstocking is becoming a legend in his own time. The 7-year-old nailed his first Grade 1 win in January in the $3 million Pegasus World Cup and for an encore racked up his 12th graded stakes victory on Saturday at Oaklawn Park in the Grade 3, $500,000 Essex Handicap.

He’s come a long way since being a $15,000 yearling purchase at Keeneland September in 2020 to an earner of $5.7 million. In between those extremes, Daniel Alonso bought Skippylongstocking for $37,000 at the Ocala Breeders’ Sales Co. spring auction of 2-year-olds in training in April 2021. He is savoring the experience of owning a horse who is 14 for 37.

“He’d never had a graded stakes winner and to get a horse like Skippy… he’s been to every single race but one,” trainer Saffie Joseph Jr. said. “He missed the Harlan’s Holiday [in December] because his sister passed away a couple of days before.

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“Every single track he’s been at with Skippy, and I think Skippy probably looks to see if he’s there.”

Skippylongstocking was scheduled to ship back to his South Florida base Sunday, according to Joseph. He said the horse could make his next start in the Alysheba at Churchill Downs.

“The goal is to get to the Breeders’ Cup Classic,” Joseph said.

Skippylongstocking is currently riding a three-race win streak that began in the Harlan’s Holiday. In the Essex, he rolled home by more than five lengths.

“It’s something on race day that brings out the best in him, and that’s probably what makes him the horse that became the overachiever that he is,” Joseph said. “I’m just so proud of him to come and do that [Saturday] – that’s the first time he’s ever won three in a row. He’s a different horse right now.

"He’s a special horse to have in our barn. A living legend."

:: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.

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