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Santa Anita

Skippylongstocking not a lock in Hollywood Gold Cup

Brad Free|May 24, 2025
Skippylongstocking.3-8-25.TK_.jpg
Tom Keyser Skippylongstocking is the class of the Hollywood Gold Cup, but the distance could pose a challenge.

ARCADIA, Calif. – If the biggest dirt race Monday at Santa Anita were a little shorter, the richest horse on the Memorial Day program might be a lock.

Skippylongstocking is not a lock in the Grade 2 Hollywood Gold Cup.

Although the race has declined in purse and prestige, it is still 1 1/4 miles, which is almost unchartered territory for Skippylongstocking, a $3.5 million earner expected to be strongly favored.

“Ten furlongs is a distance we always wanted to try with him,” trainer Saffie Joseph said. “He runs well enough going a mile and an eighth; I think he’ll handle it. Obviously, anything a horse has never done, there’s always a question mark until they do it.”

Monday is the right time to try. Skippylongstocking, an eight-time graded winner and multiple Grade 1-placed, is the class of the Gold Cup. The quality of his rivals corresponds to the prize money.

:: Playing Santa Anita? Get the most trusted data and information in horse racing! DRF Past Performances, Picks, and Clocker Reports available now.

The $200,000 purse is the lowest Gold Cup purse since 1975, when Ancient Title led wire to wire at Hollywood Park. This year, the Gold Cup field includes Packs a Wahlop, Grade 2-placed on turf; Extensive, a highly rated allowance winner; Tarantino, the likely pacesetter; Midnight Mammoth, a Grade 3 winner; Il Bellator; and Arrowthegreat.

It’s a field Skippylongstocking should defeat, notwithstanding a distant third recently in the Grade 2 Oaklawn Handicap, a race he won the year before. Circumstances were against him last out.

“We went too quick with him early,” Joseph said. “We chased a fast pace and we didn’t ride him how he likes to run.”

Skippylongstocking lost by more than seven lengths.

Irad Ortiz Jr. rides Skippylongstocking on Monday. Owned by Daniel Alonso, the 6-year-old is 10 for 31 in his career while competing at 15 racetracks. His chief rival Monday might be Packs a Wahlop, who is proven at the distance but not the surface.

Packs a Wahlop, claimed by trainer John Sadler for $50,000 in December, missed by a head last out in the Grade 2 Charles Whittingham at 1 1/4 miles on turf.

“He’s one of those turf horses that, when they ran him on the dirt before, it wasn’t really good because he’d get out-footed,” Sadler said. “But at a mile and a quarter, mile and a half, he wants to cruise. That was the farthest he’s ever run the other day.

“I just think he wants to run a long distance, and he trains really good on dirt,” Sadler said.

Reylu Gutierrez rides Packs a Wahlop, owned by Hronis Racing. Sadler and Hronis won the 2015 Gold Cup with Hard Aces and in 2018 with Accelerate, who won the Breeders’ Cup Classic that fall. The Gold Cup was downgraded to Grade 2 in 2024.

Tarantino breaks from the rail and is expected to set the pace. He placed in four graded stakes prior to a misfire last out in the Oaklawn race Skippylongstocking exits. Tarantino did not break sharply and faltered.

“He gets back there [off the pace], and he stresses out when he gets dirt in his face,” trainer Peter Eurton said.

Tarantino’s new rider is Juan Hernandez. He will go for the lead from the rail.

Extensive enters with the highest last-start Beyer Speed Figure, a 99 winning an entry-level allowance. Michael McCarthy trains Extensive, whose rider is Flavien Prat.

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

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