Daniel Alonso’s Skippy Longstocking narrowly held off a late outside challenge to win the $150,000 Harlan’s Holiday (G3) Saturday at Gulfstream Park by a head. This victory secured the durable 6-year-old a place in the $3 million Pegasus World Cup Invitational (G1) scheduled for Jan. 24.
The 1 1/16-mile race, open to horses aged three and older, serves as a preparatory event for the Pegasus World Cup’s 1 1/8-mile showdown at Gulfstream. The day’s 11-race card included five stakes races, notably the $200,000 Fort Lauderdale (G3) turf event for horses three years and older, which is a lead-up to the $1 million Pegasus World Cup Turf Invitational (G1).
Exaggerator, last year’s Harlan’s Holiday winner, aimed for a comeback but struggled recently with finishes of seventh in the Whitney (G1) at Saratoga and eighth in the Charles Town Classic (G2), where he suffered a hiccup-like diaphragmatic spasm. Trainer Safie Joseph Jr. shared cautious optimism, noting the six-year-old had never trained better despite inconsistent recent performances.
Skippy Longstocking, who claimed the Hollywood Gold Cup (G2) at Santa Anita in May but faced two setbacks in August, was ridden with strategic patience by Tyler Gaffalione. The horse stayed close behind pacemaker stablemate Hold My Bourbon through fast early fractions, briefly losing ground as the leader tired but rallying strongly in the stretch. Gaffalione and Skippy Longstocking overcame Poster—favored at 3-2 and ridden by Flavien Prat—in a thrilling final furlong duel.
This sets up an exciting clash at Churchill Downs on Nov. 9 between the seasoned Skippy Longstocking and the promising 3-year-old Godolphin-bred Poster, who recently returned from injury with an impressive allowance win. Despite Poster’s strong challenge, Skippy Longstocking’s veteran savvy secured the hard-fought win.
“I’m very proud of him and all credit goes to Saffie and his team,” Gaffalione said. “He warmed up well and gave us a courageous performance.” Skippy Longstocking completed the 1 1/16 miles in 1:43.05, marking the 10th major victory of his career and bringing his earnings over $3.7 million.
Joseph praised the horse’s resilience, saying Poster’s early momentum was thwarted when he had to adjust, allowing Skippy Longstocking to prevail. “He’s got heart—that’s something you can’t teach,” Joseph added. Skippy Longstocking, second favorite to Hold My Bourbon with a 2-1 record on Saturday, placed third in last year’s Pegasus World Cup, also won by Joseph’s stablemate White Avario.
Joseph remains hopeful for Pegasus success with a favorable post position, recalling Skippy Longstocking’s strong effort against White Avario despite a poor draw. Meanwhile, Poster, trained by Eoin Harty, missed the Road to the Kentucky Derby after a right front leg injury but showed promise finishing third in the Geoff Ruby Stakes (G3) before his setback.
Fan Take: This thrilling duel not only highlights Skippy Longstocking’s enduring competitiveness but also sets an exciting stage for the upcoming Pegasus World Cup. For horse racing fans, this rivalry symbolizes the sport’s blend of strategy, heart, and high stakes, promising memorable showdowns that keep the tradition alive and vibrant.
