Skippylongstocking

Skippylongstocking
SireExaggerator
DamTwinkling
DamsireWar Chant
SexStallion
Foaled (2019-04-02) April 2, 2019 (age 7)
CountryUnited States
ColorBay
BreederBrushy Hill, LLC
OwnerDaniel Alonso
TrainerSaffie A. Joseph, Jr.
Record39: 14 - 4 - 8
Earnings$5,893,650
Major wins
West Virginia Derby (2022)
Harlan's Holiday Stakes (2022, 2025)
Charles Town Classic (2023, 2024)
Challenger Stakes (2023, 2024, 2025)
Oaklawn Handicap (2024)
Hollywood Gold Cup (2025)
Pegasus World Cup Invitational Stakes (2026)
Essex Handicap (2026)
Last updated on July 21, 2026

Skippylongstocking (foaled April 2, 2019) is an American Thoroughbred racehorse. He is best known for winning the Grade 1 Pegasus World Cup Invitational in 2026.

Background

Skippylongstocking is a bay horse bred by Brushy Hill, LLC. He is sired by Exaggerator, out of a War Chant mare named Twinkling. Skippylongstocking was sold as a yearling at the 2021 Spring Sale of Two-Year-Olds in Training for $37,000 to Daniel Alonso.

Racing career

2021: Two-year-old season

Skippylongstocking started his career at Gulfstream Park, breaking his maiden on his third attempt before starting in the Street Sense Stakes, where he finished fourth. By placing 3rd in a December allowance race at Gulfstream, he finished his juvenile campaign with a 1-1-1-2 record in five starts.

2022: Three-year-old season

During Skippylongstocking's three-year-old season, he won the Harlan's Holiday Stakes and the West Virginia Derby, along with third-place efforts in the Wood Memorial and Belmont Stakes. For the season, his record was 3-0-2-1 in nine starts, with $724,310 total earnings.

2023: Four-year-old season

With six graded-stakes starts, Skippylongstocking went 2–1–1, with wins in the Challenger Stakes and Charles Town Classic, 2nd in the Cornhusker Handicap, and 3rd in the Breeders' Cup Dirt Mile for $816,375 in total earnings.

2024: Five-year-old season

Skippylongstocking started his five-year old season with a DNF in the Pegasus World Cup, albeit walking off. He returned two months later with a repeat win in the Challenger Stakes followed by a win in the Oaklawn Handicap; marking his first time winning two stakes in a row. He placed 3rd in the Stephen Foster and 5th in the Whitney before a repeat victory in the Charles Town Classic. In his last two starts, he placed 2nd in the Woodward Stakes and 6th in the Breeders' Cup Dirt Mile, finishing with a 3–1–1 record in 8 graded-stakes starts and $1,498,800 in total earnings.

2025: Six-year-old season

Skippylongstocking’s six-year-old campaign was highlighted by a 3-peat win in the Challenger Stakes and capturing the Hollywood Gold Cup. Although he was unable to defend his Charles Town Classic title, he won his second Harlan's Holiday Stakes to finish the season 3-0-2 in seven graded-stakes starts with $682,265 in total earnings.

2026: Seven-year-old season

Skippylongstocking tallied his first Grade 1 in the 2026 Pegasus World Cup, his fourth consecutive start in the race. The win gave him at least one victory in every stakes grade. In March, he won the Essex Handicap and became the eighth horse to win both the Essex and Oaklawn handicaps (albeit in different years).

Pedigree

Pedigree of Skippylongstocking
Sire
Exaggerator
2013 dk. b.		 Curlin
2004 ch.		 Smart Strike Mr. Prospector
Classy 'n Smart
Sherriff's Deputy Deputy Minister
Barbarika
Dawn Raid
2005 dk. b.		 Vindication Seattle Slew
Strawberry Reason
Embur Sunshine Bold Ruckus
Vevila
Dam
Twinkling
2013 dk. b.		 War Chant
1997 dk. b.		 Danzig Northern Dancer
Pas de Nom
Hollywood Wildcat Kris S.
Miss Wildcatter
Unhurried
2000 dk. b.		 Out of Place Cox's Ridge
Arabian Dancer
Laughing Erin Irish Castle
Cricket Club

References

  1. ↑ "Skippylongstocking". www.equibase.com. Retrieved 27 January 2026.
  2. ↑ "Equibase". www.equibase.com. Retrieved 2026-01-27.
  3. ↑ "OBS Video Player". www.obscatalog.com. Archived from the original on 2024-11-02. Retrieved 2026-01-27.
  4. ↑ "2021 Spring Sale of Two-Year-Olds in Training". www.obscatalog.com. Archived from the original on 2024-09-14. Retrieved 2026-01-27.
  5. ↑ "Results". www.equibase.com. Retrieved 2026-01-27.
  6. ↑ "Equibase Page". www.equibase.com. Retrieved 2026-01-27.
  7. ↑ ""2022 Harlan's Holiday Stakes Grade 3 - (race 10)"". www.equibase.com. Retrieved 2026-01-27.
  8. ↑ "2022 West Virginia Derby Grade 3 - (race 8)". www.equibase.com. Retrieved 2026-01-27.
  9. ↑ "Prairie Meadows Cornhusker Handicap 2023". www.equibase.com. Retrieved 2026-01-27.
  10. ↑ "S Pegasus World Cup Invitational S. 2024". www.equibase.com. Retrieved 2026-01-27.
  11. ↑ "$100,000 Michelob Ultra Challenger Stakes (Gr. 3)". www.equibase.com. Retrieved 2026-01-27.
  12. ↑ "Oaklawn Handicap (Gr. 2)". www.equibase.com. Retrieved 2026-01-27.
  13. ↑ "Michelob Ultra Challenger Stakes (Gr. 3)". www.equibase.com. Retrieved 2026-01-27.
  14. ↑ "Hollywood Gold Cup Stakes (Gr. 2)". www.equibase.com. Retrieved 2026-01-27.
  15. ↑ "Pegasus World Cup (Gr. 1)". Equibase.com. Retrieved 2026-03-13.
  16. ↑ "Five-generation Pedigree Table". JBIS-Search. Retrieved 2026-02-02.