Skippylongstocking Dominates Essex Handicap at Oaklawn by 5¼ Lengths

Carrying top weight of 124 pounds and a first-time jockey, Skippylongstocking made the Grade 3 Essex Handicap look like a morning workout Saturday at Oaklawn Park, pulling away from seven rivals by 5¼ lengths in the $500,000 feature to continue one of the sport's more compelling late-career surges.

Trainer Saffie A. Joseph Jr. had been forced to improvise heading into the race. The 7-year-old son of Exaggerator was originally targeted for the Grade 1 Santa Anita Handicap on March 7, but an incident while loading onto the plane to Southern California scratched those plans entirely. Regular rider Tyler Gaffalione, who had guided the horse to a 1¾-length victory over White Abarrio in the $3 million Pegasus World Cup Invitational on Jan. 24 at Gulfstream Park, was committed to nine mounts at Fair Grounds on Saturday and unavailable. That left Gulfstream-based Micah Husbands in the irons for the first time aboard Skippylongstocking, drawing post five under the heaviest impost in the field and spotting rivals six to nine pounds.

None of that mattered once the gates opened. Sent off as the 4-5 program favorite against a field that included Todd Pletcher's lightly raced Accelerize off a near-miss to 2025 Dubai World Cup winner Hit Show in the Mineshaft Stakes, and Doc Sullivan, whose stamina at 1 1/8 miles was a genuine question after a career without a win beyond a mile, Skippylongstocking settled into his rhythm and drew off decisively over the nine-furlong trip at Oaklawn.

Joseph had spent months building that patient approach. After Skippylongstocking was beaten 39¼ lengths in the Charles Town Classic on Aug. 22, 2025, a performance the trainer attributed to an electrolyte imbalance known as thumps, the connections freshened the horse and reconsidered how they were deploying him. "Between the thumps that day and sending him hard from a pace scenario, we just said after that that we were going to ride him patient," Joseph said. "We rode him more patient in the Harlan's Holiday and it worked and then we rode him patient again in the Pegasus. The horse has tactical speed to put himself in a good spot, but his best performances have been when you ride him more patiently."

The results since that recalibration have been emphatic. Skippylongstocking won the Harlan's Holiday Stakes (G3) at Gulfstream on Dec. 20, then delivered what BloodHorse called a career-best performance in the Pegasus, rushing from eighth to second on the final turn before drawing off in 1:48.87. Owner Daniel Alonso collected $1.686 million from that score; the horse paid $45.20 to win and keyed a $1 all-Joseph exacta of $133.50 over stablemate White Abarrio and jockey Irad Ortiz Jr.

The Essex was never meant to be a destination. Joseph had also weighed the $150,000 Ghostzapper Stakes (G3) at Gulfstream on March 28 before the bigger purse and familiar ground at Oaklawn settled the question. Skippylongstocking had already won the 2024 Oaklawn Handicap (G2) over this track, and the timing fit. "Obviously, it's a bigger purse," Joseph said. "It's a good spot. It's a good distance. He's won over the track already. The timing of it is good. It kind of gives us extra time to the Alysheba or if we want to go somewhere else. I hate that he got out of a rhythm because he was in a rhythm for Santa Anita, but we had to call an audible and here we are."

The stated destination is the Alysheba Stakes (G2) for older horses at 1 1/16 miles on May 1 at Churchill Downs. The Essex, which doubled as a major local prep for the Oaklawn Handicap (G2) on April 18, was the bridge. White Abarrio is pointed toward that Oaklawn Handicap, which could set up a rematch with the horse that beat him twice in three months. Duke of Duval, one of the longer-priced runners at 15-1 under Erik Asmussen for trainer Steve Asmussen, carried his own bit of history into Saturday's race: he had provided the Hall of Fame trainer with his record-extending 1,000th Oaklawn victory back on Dec. 28. Saturday belonged to someone else entirely.