Skippylongstocking tries to stay in form for Oaklawn Handicap

Seven graded stakes winners are entered in Saturday’s Grade 2, $1.25 million Oaklawn Handicap, a 1 1/8-mile event for older runners that headlines a stakes tripleheader. The Oaklawn Handicap winner receives automatic entry into the Grade 3, $250,000 Pimlico Special at 1 3/16 miles May 17 at Pimlico.

First post is 1:10 p.m. EDT, with scheduled post time for the Oaklawn Handicap, the 11th of 12 races, at 6:52 p.m. EDT. The card also features the $200,000 Bathhouse Row Stakes for 3-year-olds at 1 1/8 miles and the one-mile $200,000 Valley of the Vapors Stakes for 3-year-old fillies.

Program favorite Skippylongstocking is trying to give Florida-based trainer Saffie Joseph Jr. his first career Oaklawn victory.

Although Skippylongstocking is a multiple graded stakes winner of $1,654,185, he has never won consecutive races in his career. He exits a 2 1/2-length victory in the $100,000 Challenger Stakes (G3) for older horses March 9 at Tampa Bay Downs.

Skippylongstocking’s 22-race resume includes a front-running five-length victory in the $1 million Charles Town Classic (G2) at 1 1/8 miles Aug. 25 at Charles Town and a third-place finish in the $1 million Breeders’ Cup Dirt Mile Nov. 4 at Santa Anita.

Late-running millionaire Red Route One exits a victory in the $500,000 New Orleans Classic (G2) for older horses at 1 1/8 miles March 23 at Fair Grounds for Hall of Fame trainer Steve Asmussen. Red Route One made four starts last year at Oaklawn, including three in Kentucky Derby qualifying races. Red Route One capped his stay in Hot Springs with a victory in the $200,000 Bathhouse Row Stakes for 3-year-olds at 1 1/8 miles in April.

“Obviously, very nice win in New Orleans last time out,” Asmussen said. “This is a very good opportunity for him. Keeps moving forward.”

Hall of Fame trainer Bob Baffert seeks his third seven-figure victory this season at Oaklawn with Grade 3 winner Reincarnate.

Reincarnate, then under the care of trainer Tim Yakteen, ran in two Kentucky Derby qualifying races last year at Oaklawn, finishing a troubled third in the $1 million Rebel Stakes (G2) and third in the $1.25 million Arkansas Derby (G1). Red Route One was second and sixth, respectively, in both races.

Reincarnate closed 2023 with a ninth-place finish in the $250,000 Twilight Derby (G2) on the turf Nov. 4 at Santa Anita. In his only start this year, Reincarnate finished third, beaten 2 1/2 lengths, in the $400,000 Santa Anita Handicap (G1) at 1 1/4 miles March 3 at Santa Anita. It was his first race against older horses.

“He ran a big race off the layoff in the Big ’Cap,” Baffert said. “He’s been up there before. He shows up every time. I think it’s a good spot. I think he will fit with those horses. It’s going to be tough, but he’s doing pretty well.”

Regally bred Highland Falls exits a fourth-place finish in the Santa Anita Handicap, his stakes debut, for trainer Brad Cox and breeder/owner Godolphin. The 4-year-old colt is by two-time horse of the year Curlin out of Breeders’ Cup Distaff Champion Round Pond, both multiple Oaklawn stakes winners. Highland Falls, beaten 2 3/4 lengths in the Santa Anita Handicap, will be cutting back to nine furlongs in his sixth lifetime start.

“I think he can handle it,” Cox said. “Listen, I think most of these races that are run, these Grade 1s in this division, are run at a mile and an eighth. Obviously, the Breeders’ Cup is a mile and a quarter. We’re hoping he can establish himself as one of the better handicap horses in the country. He’s obviously light on seasoning, but hopefully he can have a big year and see where he takes us.”

Godolphin won last year’s Oaklawn Handicap with Proxy, who edged millionaire Last Samurai by a head. Now with trainer Eddie Milligan Jr., Last Samurai came off a lengthy layoff to finish a tiring sixth in the $500,000 Oaklawn Mile (G3) March 30.

Last Samurai won the 2022 Oaklawn Handicap when trained by Dallas Stewart. In addition to finishing second in the 2023 Oaklawn Handicap, Last Samurai won Oaklawn’s $600,000 Razorback Handicap (G3) and $500,000 Essex Handicap (G3) last year for Hall of Fame trainer D. Wayne Lukas.

“He’s doing well, working well,” said Milligan, who trains Last Samurai for Arkansan Kevin Horton. “I just don’t know if he’s a 100 percent ready to compete with that group, as consistent as he was last year. I think after this race, yes, I think we’ll be back on track with him.”

Florida-based Octane returns to Oaklawn after winning the Feb. 24 Razorback (G3) in his last start.

Instant Coffee, a former Cox runner, is a Grade 2 winner. Now based in Florida with trainer Jose D'Angelo, Instant Coffee recorded a 5-furlong workout April 12 at Oaklawn in preparation for the Oaklawn Handicap.

Grade 2 winner Double Crown, Magic Tap, Guntown and County Final complete the field. The Oaklawn Handicap carries a record purse in 2024 after previously being worth $1 million.