Skippylongstocking has big anniversary celebration with Oaklawn Handicap

HOT SPRINGS, Ark. – Skippylongstocking was a $37,000 purchase by Daniel Alonso at the Ocala Breeders’ Sales auction of 2-year-olds in training on April 20, 2021.

Fast forward to Saturday, April 20, 2024, and he pushed his career earnings past $2 million with a powerful victory in the Grade 2, $1.25 million Oaklawn Handicap.

“That’s pretty ironic,” winning trainer Saffie Joseph Jr. said. “I knew I bought him in April in the sale. I didn’t know it was April 20. That’s pretty special. I mean, God is good.

“Here we are, three years later, and look at the run he’s taken us on. Skippy’s taken us all over. He’s run at a lot of tracks. He’s just been ultra-consistent. He’s one of those war horses. So thank him and thank God for keeping him healthy.”

Skippylongstocking ($7.60) was making his first start at Oaklawn and broke well and settled just off pacesetter County Final. He tracked County Final through fractions of 23.21 seconds for the opening quarter, 47.62 for the half-mile and 1:11.99 for six furlongs.

:: Bet the races with a $200 First Deposit Match + FREE All Access PPs! Join DRF Bets.

Skippylongstocking took over from there, and increased his advantage to the wire for a two-length win over Highland Falls. It was another three lengths back in third to Red Route One. Skippylongstocking covered the 1 1/8 miles on a fast track in 1:49.

“He broke really clean,” winning rider Jose Ortiz said in a post-race interview conducted by Oaklawn. “The other horse had speed, went to the lead, and I was happy to just track. My horse was relaxed every step of the way, so I was very happy. And when I asked him to go, he responded really well.”

The win was an important one for Skippylongstocking on a number of different levels, Joseph said. It came two starts after he was pulled up in the Pegasus World Cup Invitational after breaking from post 12 in the January race at Gulfstream Park. Skippylongstocking returned to win the Grade 3 Challenger at Tampa Bay Downs in March in what was a rebuilding race, Joseph said. Skippylongstocking then targeted the Oaklawn.

“He was able to come away from there and put himself in a perfect spot,” Joseph said. “He’s the kind of horse who wants to sit forward, but he doesn’t want you sending him hard. We did that in the Pegasus because we were drawn so bad and we kind of messed up there. We learned from it.

“After the Pegasus we had to gather our thoughts and go over the horse properly and everything checked out well. Tampa put us back on track, but still, you had reservations. And then today put an exclamation point on it – Skippy’s back to his best, if not better. I think it was his best race ever, how he finished it off.”

Skippylongstocking earned $637,500 for Alonso on Saturday to improve his career record to eight wins from 23 starts for earnings of $2,291,685. He is a 5-year-old by Exaggerator.

Joseph said Skippylongstocking will head home to South Florida with plans to be determined.

“Nothing set after this,” he said. “This was a huge race – this was big in its own sense. Obviously, we’d like to get back to Charles Town to repeat there in the Charles Town Classic. Where we go in between, I don’t know yet.”

Skippylongstocking was the 122-pound highweight and the favorite in the Oaklawn Handicap.

Racing resumes Sunday.

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