By Stefanie Grimm
It came down to the top two betting choices as 6-year-old Skippylongstocking (Exaggerator) and 3-year-old Godolphin homebred and 'TDN Rising Star, presented by Hagyard' Poster (Munnings) threw down through the final furlong but, in the end, Skippy got the better of his younger, favored rival to capture the GIII Harlan's Holiday at Gulfstream Park Saturday.
The traditional prep for next month's GI Pegasus World Cup Invitational, the Harlan's Holiday was Skippylongstocking's first race back since a case of the thumps saw him fade to eighth on a hot night in West Virginia in the Charles Town Classic in August. Should he make the gate, it would be his fourth straight Pegasus World Cup, with his best effort coming last year when third behind stablemate White Abarrio (Race Day) and new Gainesway stallion Locked (Gun Runner).
It's been an up and down campaign for the true war horse and $3.6m earner who made his 35th overall start Saturday. His first four starts over four different tracks showed promise as he kicked things off with his aforementioned third in the Pegasus before winning the GIII Challenger Stakes at Tampa. Another third followed in the GIII Oaklawn Handicap before he shipped to California to take the GII Hollywood Gold Cup at Santa Anita in May. Things went awry from there as Joseph sent him into deep water at Saratoga in the GI Whitney Stakes where he wound up seventh before that medical setback at Charles Town sidelined him for much of the autumn season.
Breaking from the inside Saturday as one of two Saffie Joseph Jr. runners in the field, Skippy came away in good order just outside of stablemate Hold My Bourbon (Anchor Down) was who intent to lead on the fence under Irad Ortiz Jr. That rival rocketed out to a clear, mult-length lead around the clubhouse turn and up the backstretch, keeping things fast up front through fractions of :22.87 and :45.95. The rest of the field seemed happy to let that runner go as Skippy sat third in close company with Chilean invader Con Compania (Chi) (Awesome Patriot) just to his inside.
As Hold My Bourbon began to come back past the half-mile pole, room opened for the top runners to take a crack but Skippy got caught boxed in and needing a seam. Having to navigate traffic, Tyler Gaffalione was patient and guided the 2-1 second choice out and around the fading pacesetter to set up a duel with Poster who circled up on the far outside with a big move from the back of the pack.
That pair linked up at the quarter pole and bobbed heads in a gutsy duel to the first finish line with Skippylongstocking just getting a narrow advantage in the final strides to win. 26-1 longshot Catalytic (Catalina Cruiser) filled out the trifecta. This was Skippy's second win in the Harlan's Holiday–he first took it as a 3-year-old in 2022 en route to his first start in the Pegasus World Cup.
“He came back, and you never know if they're going to come back. When they run two bad races, you never know. You just try to observe what he's telling you, and he was training as good as he has ever trained in his life.,” Joseph Jr. said. “He's 6 going on 7, but trust me, his works were as good as he ever worked, and we were quietly optimistic that he would run well. But you never know. I think you have to ride the horse patient. I think that's one of the keys to him. Apart from the thumps last time, we sent him hard against a huge bias that day and today he redeemed himself.”
“He got his momentum stopped,” Joseph continued. “He ran into the back of my other horse that was backing up. Prat did a good job of seeing him there and actually waiting to make sure he got stuck, but Tyler was able to split,” Joseph said. “Poster had all the momentum and then he had to kind of dig and rally. It's a gutsy performance and that's the kind of horse he is. That's why he's had the career he's had, because he has the heart. That's something you can't teach.”
And as for a fourth-straight try at the Pegasus?
“If the draw's good, he can win the Pegasus there's no doubt about it,” Joseph said. “This year, he ran huge against White Abarrio from a terrible post. If he draws good and gets the right setup, it's not impossible. We'll see.”
Pedigree Note:
Skippylongstocking continues to be the flag bearer for his Preakness-winning sire Exaggerator. His dam, the War Chant mare Twinkling, placed in a trio of turf races in her own track career but has seen a higher level of success in the breeding shed with four winners from as many to make the races.
And while Skippy is clearly the class of his siblings, Twinkling has also produced SW/GSP Olivia Twist (Mshawish) who brought $500,000 from Jim Cone at the Keeneland November Sale just last month carrying her first foal by Arabian Knight. Yet another of Skippy's half-siblings is SW/GSP Moonlite Strike (Liam's Map) who made an early run at the Road to the Kentucky Derby with a third in the GII Tampa Bay Derby back in 2021.
Buyers have taken notice as Twinkling's last few foals have brought steep sums in the sales ring. Her 2-year-old Authentic filly went Shadwell's way for $550,000 at Keeneland September last year while her yearling Not This Time filly is now in the hands of Mike Repole for $1,000,000 out of the September Sale. Another of Skippy's half-sisters, Always Twinkling, went through the Fasig-Tipton ring last month, bringing $275,000 shortly after her weanling Cody's Wish filly brought $440,000.
After failing to take on a Curlin cover for this year, Twinkling returned to the Hill 'n' Dale legend for her 2026 cover.
Saturday, Gulfstream Park
HARLAN'S HOLIDAY S.-GIII, $150,000, Gulfstream, 12-20, 3yo/up, 1 1/16m, 1:43.05, ft.
1–SKIPPYLONGSTOCKING, 126, h, 6, by Exaggerator
1st Dam: Twinkling, by War Chant
2nd Dam: Unhurried, by Out of Place
3rd Dam: Laughing Erin, by Irish Castle
($15,000 Ylg '20 KEESEP; $37,000 2yo '21 OBSAPR). O-Daniel
Alonso; B-Brushy Hill, LLC (KY); T-Saffie A. Joseph, Jr.; J-Tyler
Gaffalione. $91,140. Lifetime Record: MGISP, 35-12-3-7,
$3,775,250. *1/2 to Olivia Twist (Mshawish), SW & GSP,
$321,579; Moonlite Strike (Liam's Map), SW & GSP, $175,205.
Werk Nick Rating: A+++ *Triple Plus* Click for the
eNicks report & 5-cross pedigree.
Free Equineline.com catalogue-style pedigree.
2–Poster, 118, c, 3, Munnings–Pin Up, by Tapit. 'TDN Rising
Star, presented by Hagyard' O/B-Godolphin (KY); T-Eoin G.
Harty. $29,400.
3–Catalytic, 121, c, 4, Catalina Cruiser–One Show Only, by
Distorted Humor. ($70,000 Wlg '21 KEENOV; $125,000 Ylg '22
FTSAUG). O-Tami Bobo; B-Fred W. Hertrich (KY); T-Antonio
Sano. $14,700.
Margins: HD, 5HF, 2 3/4. Odds: 2.40, 1.50, 26.40.
Also Ran: Classic of Course, Hold My Bourbon, Con Compania (Chi), Racing Driver. Click for the Equibase.com chart or the TJCIS.com PPs. VIDEO, sponsored by FanDuel TV.
Skippy IS Skippy today! 🏃🏻 SKIPPYLONGSTOCKING ($6.80) overcomes traffic to win the $150,000 Harlan's Holiday (G3) at @GulfstreamPark under @Tyler_Gaff for trainer @SaffieJosephJr and owner Daniel Alonso.
The Ft Lauderdale Stakes (G3) is next. Bet with @FanDuel Racing. pic.twitter.com/6OusI1D3BQ
— FanDuel Racing (@FanDuel_Racing) December 20, 2025
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