Daniel Alonso’s multiple graded stakes winner Skippylongstocking (Exaggerator – Twinkling, by War Chant) fought off a stretch-long challenge to prevail by a head in the $150,000 Harlan’s Holiday (G3) at Gulfstream Park Dec. 20, leading the slate of stakes-winning OBS graduates for the week.

(Lauren King photo)
With the victory, the 6-year-old horse earned a berth for the $3 million Pegasus World Cup Invitational (G1) Jan. 24. The son of Exaggerator, who also captured the 2022 Harlan’s Holiday, notched his 10th graded stakes victory during a career in which he’s earned more than $3.7 million under the care of trainer Saffie Joseph, Jr.
“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,” Joseph told Gulfstream Park publicity. “But you never know. I think you have to ride the horse patient. I think that’s one of the keys to him.”
Skippylongstocking was purchased by Alonso for $37,000 out of the Top Line Sales consignment at the 2021 OBS April Sale after breezing an eighth in :10 2/5.
The Dec. 20 card at Gulfstream Park also saw Ms. Bucchero (Bucchero-Give Glory to God, by Mutakddim), owned and trained by Diane Morici, rally along the inside down the stretch to win the $125,000 Sugar Swirl, a race where five of the six entrants were OBS grads.
Nic’s Style was second while favorite and defending race winner Mystic Lake was third.
A 5-year-old mare by OBS grad and leading New York sire Bucchero, Ms. Bucchero was an RNA from the consignment of Nice and Easy Thoroughbreds at the 2022 OBS April Sale after breezing in 10.0.
At Laurel Park Dec. 20, Golden Lion Racing’s Complexity Jane (Complexity –Bestinthebusiness, by Ghostzapper) displayed determination to score the victory in the $100,000 Carousel Stakes. Trained by Brittany Russell, the daughter of Complexity was purchased by Sycamore Hall Thoroughbreds for $170,000 at the 2024 OBS March Sale from the Scanlon Training & Sales consignment after breezing in :10 1/5.
At Turfway Park Dec. 21, WinStar Farm’s Canadian champion Caitlinhergrtness (Omaha Beach – Belatrix, by Giant’s Causeway) proved much the best in the $219,000 My Charmer Stakes.
Trained by Kevin Attard, Caitlinhergrtness became racing’s newest millionaire with earnings of $1,071,569. Her overall record stands at 17-6-4-2. Last year’s King’s Plate winner was consigned by Off the Hook to the 2023 OBS April Sale where she sold for $375,000 to Maverick Racing & Siena Farms after breezing in :10 flat.
At Oaklawn Park Dec. 19, Randy Patterson, Sam M. Vogel and Joe Morgan’s Dreaminblue (Street Boss-Dreamy Blues, by Curlin) made a three-wide move approaching the quarter pole before drawing off down the lane to win the $135,000 Silks Overnight Stakes by three lengths.
Trained by Randy Morse, Dreaminblue stopped the clock in 1:09.10, the quickest of the first four days of the 2025-2026 Oaklawn season. He was purchased by Patterson for $120,000 at the 2024 OBS June Sale from the McKathan Bros. Sales consignment after breezing in :10 1/5.
