Trainer Saffie Joseph Jr. and jockey Irad Ortiz Jr. had an amazing hour at Santa Anita Park May 26. One race after the terrific Be Your Best captured the Gamely Stakes (G1T), the venerable Skippylongstocking added the Hollywood Gold Cup (G2), though he had to deal with a persistent Midnight Mammoth to get the job done.
Skippylongstocking demonstrated that no matter what track Joseph ships him to, he will be ready to give his all. He was making his second start at Santa Anita—the first coming when third in the 2023 Breeders' Cup Dirt Mile (G1)—but he proves over and over again his willingness to travel and add to a bankroll of more than $3.6 million.
Though he frequently sets the pace, Skippylongstocking was tackling 1 1/4 miles in the Gold Cup rather than his more usual 1 1/8 miles. Thus, Ortiz let the 4-5 favorite settle midpack of the seven-horse field while Packs a Wahlop led, a length ahead of Midnight Mammoth, through fractions of :22.55, :46.33, and 1:10.87.
"We didn't want him on the lead today," said Joseph by phone after the race. "We're kind of learning that the more patient we can ride him, he's a better horse."
One thing that did concern Joseph was that Skippylongstocking was racing wide around the first turn.
"When he's three or four wide, that's not kind of his trip," Joseph said.
Ortiz asked Skippylongstocking to start moving up into the second turn, and the horse delivered his usual professional response. Skippylongstocking came around the leaders and took over at the top of the stretch, looking like he could coast home.
By then, Packs a Wahlop was backing up, but Midnight Mammoth refused to give up. Skippylongstocking and Midnight Mammoth battled throughout the stretch. Though Midnight Mammoth gamely stuck to the invader, Skippylongstocking prevailed by three-quarters of a length, stopping the timer in 2:01.64. Extensive finished six lengths behind Midnight Mammoth in third.
"Once he got to the top of the lane, I felt that he was going to put away the horse, but that horse was very game," Joseph said.
Ortiz noted that Skippylongstock "relaxed for me beautifully" early.
"We were planning to stay back and not be on the lead," the jockey said. "I was happy where he was, and he went on from there. The horse on the inside was fighting back, and my horse was fighting back as well."
Owned by Daniel Alonso, Skippylongstocking could return to California in the fall for the Breeders' Cup at Del Mar. He has twice competed in the Dirt Mile—finishing sixth at Del Mar last year following his third at Santa Anita—but Joseph has said that if the horse did well at the 1 1/4-mile distance, he might consider the Breeders' Cup Classic (G1). The trainer also said that the connections hope to race the 6-year-old in 2026.
Skippylongstocking has certainly proved a bargain for Alonso, who paid only $37,000 for him at the 2021 Ocala Breeders' Sales Company's Spring 2-Year-Old Sale. Brushy Hill bred Skippylongstocking in Kentucky from the War Chant mare Twinkling, whose other foals include stakes winners Olivia Twist and Moonlite Strike.
Skippylongstocking is the first 2025 black-type winner sired by Exaggerator, who began his racing career at Santa Anita and won the 2016 Santa Anita Derby (G1). Exaggerator went on to add that year's Preakness Stakes (G1) and Haskell Invitational (G1). He stands for $5,000 at Elite Thoroughbreds Farm near Folsom, La.
