Key Points
- Grade 1 Pegasus World Cup Invitational winner Skippylongstocking will retire to Amsterdam Two Farm in Middleburgh, New York, for the 2027 breeding season.
- The son of Exaggerator has earned more than $6 million and has recorded 12 graded stakes victories during his racing career.
- Amsterdam Two has announced an initial stud fee of $3,500, although the fee could be increased after his performance in the Breeders’ Cup Classic.
- Skippylongstocking is scheduled to contest the Breeders’ Cup Classic at Keeneland on October 31 before attempting to defend his Pegasus World Cup title in January.
- The horse has won major dirt races including the Charles Town Classic, Oaklawn Handicap and Hollywood Gold Cup.
- He finished third in both the 2022 Belmont Stakes and the 2023 Breeders’ Cup Dirt Mile.
- Amsterdam Two manager Ken Williams highlighted the horse’s physical size and described him as an imposing stallion prospect.
- Owner Daniel Alonso will retain a significant ownership interest and plans to breed at least 10 mares to Skippylongstocking in 2027.
- Trainer Saffie Joseph Jr. said the horse has made 32 consecutive starts against graded stakes company.
- Michael Slezak and Matt Bowling of Bowling Bloodstock brokered the agreement, with Slezak also set to handle the stallion’s marketing.
- Contracts for seasons, shares and lifetime breeding rights signed before November 1 will be honoured at their current rates.
- Amsterdam Two said a Breeders’ Cup win or placing could result in higher breeding fees.
Amsterdam Times News (ATN) October 2, 2026 – Grade 1 winner and multimillionaire Skippylongstocking is set to begin his stallion career at Amsterdam Two Farm in Middleburgh, New York, following the conclusion of his racing career, with the horse scheduled to stand for an initial fee of $3,500 in 2027. The announcement comes as the seven-year-old prepares for the final stages of his racing campaign, which are expected to include the Breeders’ Cup Classic at Keeneland on October 31 and an attempted defence of his Pegasus World Cup Invitational title at Gulfstream Park in January.
According to Thoroughbred Daily News, the agreement was brokered by Michael Slezak and Matt Bowling of Bowling Bloodstock. The move will take Skippylongstocking from the racetrack into the breeding operation at Amsterdam Two after a career in which he has earned more than $6 million and collected 12 graded stakes victories.
New York Thoroughbred Breeders reported on October 2 that the horse had earned more than $6 million, won a dozen graded stakes and recorded 10 triple-digit Beyer Speed Figures to date. Its report also confirmed that the $3,500 fee could change after his Breeders’ Cup Classic performance.
Why Is Skippylongstocking Moving To Amsterdam Two Farm For 2027?
The decision follows the planned conclusion of Skippylongstocking’s racing career and establishes his next role within New York’s Thoroughbred breeding industry.
Amsterdam Two Farm, based in Middleburgh, has selected the horse for its 2027 stallion roster after his extended career in top-level dirt racing. The farm announced that he will stand for $3,500, subject to the outcome of his remaining major races.
The horse’s physical presence was specifically highlighted by Amsterdam Two manager Ken Williams.
“At nearly 17 hands, Skippylongstocking is about as imposing as a stallion prospect can be,” Williams said, according to the announcement reported by Thoroughbred Daily News. Williams added that the horse’s size and scope would be relevant to breeders considering him as a stallion.
The planned move also places a high-profile racehorse within New York’s breeding programme at a time when the state is promoting its racing and breeding incentives.
What Is Skippylongstocking’s Racing Record?
Skippylongstocking has built his record primarily through dirt racing against graded company.
According to Thoroughbred Daily News, all 12 of his career stakes victories have come on dirt. His wins include two consecutive editions of the Grade 2 Charles Town Classic, the Grade 2 Oaklawn Handicap, the Grade 2 Hollywood Gold Cup, the Grade 3 West Virginia Derby, the Grade 3 Essex Handicap, two editions of the Grade 3 Harlan’s Holiday and three consecutive editions of the Grade 3 Michelob Ultra Challenger Stakes.
His victory in the Michelob Ultra Challenger Stakes at Tampa Bay Downs was particularly notable because he set a track record of 1:41.2 for 1 1/16 miles.
His Oaklawn Handicap victory also produced a career-high 107 Beyer Speed Figure, according to the published announcement.
New York Thoroughbred Breeders described him as a track-record setter and noted that he had accumulated 10 triple-digit Beyer Speed Figures by the time of the announcement.
The horse has also competed successfully at some of North America’s most prominent meetings. His record includes third-place finishes in the 2022 Belmont Stakes and the 2023 Breeders’ Cup Dirt Mile.
How Important Was Skippylongstocking’s 2026 Pegasus World Cup Victory?
The defining victory of Skippylongstocking’s 2026 campaign came in the Grade 1 Pegasus World Cup Invitational Stakes at Gulfstream Park.
New York Thoroughbred Breeders reported that Skippylongstocking won the $3 million race over 1 1/8 miles by 1¾ lengths. The field included Grade 1 winners White Abarrio, Tappan Street, Full Serrano and British Isles.
Paulick Report, in a report identified as an edited press release, likewise described the Pegasus World Cup as the horse’s signature victory of 2026. It reported that he defeated a 12-horse field and used his late acceleration to secure the win.
The Pegasus victory also provides the immediate basis for the horse’s planned final racing programme. The announcement states that he is expected to try to defend that title in January after contesting the Breeders’ Cup Classic.
What Are Skippylongstocking’s Final Racing Plans?
Skippylongstocking is expected to have two major opportunities before entering stud.
The first is the Breeders’ Cup Classic at Keeneland on October 31. Following that race, current plans call for him to return to Gulfstream Park in January to attempt a repeat victory in the Pegasus World Cup Invitational.
He will contest those races for the partnership of Daniel Alonso and Joe Tesiero’s Amsterdam Two Stables.
The outcome of the Breeders’ Cup Classic also has a direct connection to his advertised breeding fee. Amsterdam Two has set the initial fee at $3,500 but has indicated that a win or placing in the Breeders’ Cup Classic could lead to an increase.
Williams said that breeding contracts covering seasons, shares and lifetime breeding rights signed before November 1 would be honoured at the rates available when those agreements were made.
This means the horse’s final major race of the season could have consequences beyond his racing record, particularly for the commercial terms attached to his first season at stud.
What Did Daniel Alonso Say About The Horse’s Move To New York?
Owner Daniel Alonso said Skippylongstocking had taken his family on what he described as an extensive racing journey across the United States.
Alonso will retain a significant ownership stake in the horse after the transition to stud. He also plans to breed at least 10 mares to Skippylongstocking during the 2027 season.
According to the published announcement, Alonso pointed to the horse’s victories across Florida, California, Arkansas and West Virginia, as well as his ability to compete over distances ranging from one mile to 1¼ miles.
Alonso also linked the decision to New York’s wider racing and breeding environment. He referred to the renovation of Belmont Park and the state’s purse parity for New York-breds, along with breeders’ and stallion owners’ awards, as factors supporting the decision to launch Skippylongstocking’s stud career in New York.
The comments place the stallion decision within the broader context of New York’s attempt to maintain and develop its Thoroughbred breeding sector.
What Has Trainer Saffie Joseph Jr Said About Skippylongstocking?
Trainer Saffie Joseph Jr. has emphasised the consistency of Skippylongstocking’s racing career.
Joseph said the horse’s ability to compete at the highest level had made him the type of horse trainers want in their stables. He also highlighted a sequence of 32 consecutive starts against graded stakes company.
Joseph added that he looked forward to training the horse’s offspring, referring to the possibility of Skippylongstocking’s first crop reaching the racetrack in the years ahead.
The 32-start figure is significant within the context of the announcement because it illustrates the length of the horse’s exposure to graded stakes competition rather than representing a single-season campaign.
The Breeders’ Cup points information also records Skippylongstocking’s 2026 campaign, including his Pegasus World Cup victory, an Essex Handicap win and graded stakes results later in the year.
What Makes Skippylongstocking’s Pedigree Relevant To Breeders?
Skippylongstocking is by Exaggerator and out of Twinkling, a mare by War Chant.
Michael Slezak, who brokered the stallion agreement with Matt Bowling and will handle marketing for Skippylongstocking, said the horse’s pedigree was an important element in Amsterdam Two’s decision.
Slezak pointed to Twinkling’s record as a producer. According to the announcement, four of her first six foals of racing age have earned graded black type on dirt surfaces. The announcement also identified a $1 million Not This Time juvenile in the pipeline for Repole Stable.
Slezak also placed Skippylongstocking within the broader bloodline of Exaggerator, who is described in the announcement as a Preakness-winning son of Curlin.
The report referenced several young Curlin sons and grandsons, including Cody’s Wish, Elite Power, Journalism, Golden Tempo, Dornoch, Mage, Muth and Blazing Sevens, when discussing the bloodline’s presence within contemporary Thoroughbred breeding.
These comments represent Slezak’s assessment of the pedigree rather than an established outcome for Skippylongstocking’s future progeny.
When Will Breeders Be Able To See Skippylongstocking?
Amsterdam Two plans to display Skippylongstocking to interested breeders and racing industry participants on Sunday, October 11.
The scheduled viewing is from 4:30pm to 5pm outside the horse’s barn near Saratoga’s Oklahoma Training Track. The location is across the street from the Fasig-Tipton Saratoga Fall Mixed Sale grounds.
The showing provides breeders with an opportunity to inspect the stallion before his first breeding season.
The timing also places the appearance shortly before the November 1 date associated with the current breeding contracts. Amsterdam Two has stated that contracts signed before that date will be honoured at their current rates.
Who Brokered The Skippylongstocking Stallion Agreement?
The agreement was brokered by Michael Slezak and Matt Bowling of Bowling Bloodstock.
Slezak is also expected to handle marketing for Skippylongstocking as the horse begins his stud career.
The role involves presenting the horse’s racing record, physical characteristics and pedigree to prospective breeders. The published reports identify Slezak’s comments about Twinkling’s production record and the Exaggerator-Curlin bloodline as part of the rationale surrounding the stallion’s commercial positioning.
The involvement of Bowling Bloodstock completes the commercial arrangement that will move Skippylongstocking from his racing partnership into the breeding operation at Amsterdam Two.
What Does The Move Mean For New York Breeding?
Skippylongstocking’s arrival gives Amsterdam Two a Grade 1-winning, multimillion-dollar racehorse for its 2027 stallion roster.
For New York breeders, the horse’s presence adds another stallion option with an established record in graded dirt racing. His victories across different tracks and distances form the principal racing evidence being presented to prospective breeders.
Alonso’s decision to retain an ownership stake and breed at least 10 mares to the horse also establishes a direct connection between his racing ownership and his first breeding season.
The move also comes against the backdrop described by Alonso concerning the renovated Belmont Park and New York’s breeding incentives. Those incentives include purse arrangements for New York-breds and awards for breeders and stallion owners, according to the announcement.
The commercial value of the arrangement, however, will depend on the horse’s final racing performances, the number and quality of mares booked to him and the subsequent performance of his offspring. Those outcomes have not yet been established.
What Is The Background To Skippylongstocking’s Retirement Plan?
Skippylongstocking is a 2019-born son of Exaggerator and Twinkling, by War Chant. His career has developed over several seasons and has included repeated appearances in graded stakes races.
His 2026 season brought his most prominent victory when he won the Grade 1 Pegasus World Cup Invitational at Gulfstream Park. The horse has also accumulated victories in the Charles Town Classic, Oaklawn Handicap, Hollywood Gold Cup and several Grade 3 races.
His earlier career included third-place finishes in the 2022 Belmont Stakes and the 2023 Breeders’ Cup Dirt Mile. His racing record therefore includes both major wins and placings in some of North America’s established graded stakes contests.
The move to Amsterdam Two follows a pattern common in Thoroughbred racing in which successful racehorses transition to breeding after their competitive careers. In Skippylongstocking’s case, the transition is planned rather than immediate, because he is expected to race in the Breeders’ Cup Classic and then attempt another Pegasus World Cup appearance.
How Could The Development Affect Breeders And New York Racing?
For breeders considering Skippylongstocking for the 2027 season, the immediate factors will include his final racing results, the $3,500 initial fee, his pedigree and physical characteristics, and the terms offered by Amsterdam Two.
The farm has explicitly connected the potential fee structure to his Breeders’ Cup Classic result. A win or placing could lead to an increase, while agreements made before November 1 are set to remain at their existing rates.
For New York racing, the development brings a Grade 1 winner into the state’s stallion population and aligns with the breeding incentives cited by Alonso. However, the long-term contribution of the horse to the New York breeding programme cannot yet be measured.
The principal future test will be the performance of Skippylongstocking’s progeny once they begin racing. Until then, the available evidence consists of his own racing record, pedigree, physical characteristics and the commercial terms announced by Amsterdam Two.
What Could Happen Next For Skippylongstocking?
The immediate sequence is clear: Skippylongstocking is scheduled to compete in the Breeders’ Cup Classic at Keeneland on October 31, followed by an intended attempt to defend his Pegasus World Cup title in January. After those races, he is expected to enter the breeding programme at Amsterdam Two for the 2027 season.
His Breeders’ Cup result could affect his advertised stud fee, according to Amsterdam Two. A win or placing could lead to higher fees, while existing contracts signed before November 1 will be honoured at their agreed rates.
For breeders and New York racing participants, the longer-term significance will depend on factors that remain unresolved, including the level of demand for his services, the mares booked to him and, eventually, the racing performance of his offspring.
At present, the confirmed development is that a horse with more than $6 million in earnings and 12 graded stakes victories is scheduled to begin his stud career in New York in 2027, with Amsterdam Two setting an initial fee of $3,500.
