Skippylongstocking targets Monmouth Cup debut after Pegasus World Cup win

Skippylongstocking is headed to the $350,000 Grade 3 Monmouth Cup on July 18, and the Haskell Day race will put another stamp on a season that already includes a Grade 1 win and a growing reputation for durability. The Saffie Joseph Jr. runner will be making his first start at Monmouth Park, which also means the Oceanport track becomes the 16th different racetrack on his resume.

That kind of travel is part of the story with Skippylongstocking. The 7-year-old son of Exaggerator was bought for just $37,000 at the 2021 OBS April Sale after breezing an eighth in :10 2/5, then turned into a major player on the dirt stakes circuit for owner Daniel Alonso. He has banked more than $5.8 million from 14 wins in 38 starts, and the Monmouth Cup offers another chance to add to a campaign that has already stretched across the winter and spring.

His biggest score came in January when he won the Pegasus World Cup by 1 3/4 lengths over White Abarrio, finally getting the first Pegasus victory of his career after previous attempts fell short. The 10th running of the Pegasus World Cup program featured 13 races and $5.675 million in purses, and Skippylongstocking’s win pushed him back into the center of the older-horse division. He followed that with a Grade 3 Essex Handicap victory at Oaklawn Park in March, then most recently finished second in the Grade 2 Alysheba on Kentucky Oaks Day.

Joseph has already put him back to work, sending him three furlongs in :38.90 at Palm Meadows, with another drill planned before he joins the barn at Saratoga. That is the profile Monmouth will test: not just speed, but stamina, resilience and the ability to stay dangerous through a long season.

Equibase lists the Monmouth Cup as a Grade 3 at 1 1/8 miles on dirt for 3-year-olds and up, a race with roots back to 1976. Rule set the record at 1:37.71 in 2012, and Surface to Air won the 2025 renewal. For Skippylongstocking, a strong run would do more than collect another graded paycheck. It would further establish him as one of the sport’s most battle-tested older dirt horses and keep him on the path to bigger late-season targets.