Pay Billy

Connections

Owner: RKTN Racing LLC
Breeders: WinStar Farm, LLC
Trainer: Michael E. Gorham
Jockey: Raul E. Mena

Pay Billy: 2025 Preakness Stakes Contender Profile

Pay Billy, a 3-year-old bay colt by Improbable out of Harlington’s Rose, enters the 2025 Preakness Stakes with a formidable 4-for-8 record, including three stakes victories in 2025 at Laurel Park. Trained by Michael E. Gorham and ridden by Raul E. Mena, Pay Billy has shown consistent improvement, culminating in a gritty win in the Federico Tesio Stakes on April 19, 2025, earning a 93 speed figure. His front-running style and resilience in stretch duels, as seen in the Private Terms Stakes and Miracle Wood Stakes, make him a contender to watch. Sired by Improbable, a Grade 1 winner, and out of a Harlington mare with a sturdy pedigree, Pay Billy has the speed and stamina to tackle the 1 3/16-mile Preakness Stakes at Pimlico on May 17, 2025.

Pedigree

Pay Billy
├── Sire: Improbable
│   ├── Sire: City Zip
│   └── Dam: Rare Event
└── Dam: Harlington's Rose
    ├── Sire: Harlington
    └── Dam: A Rose For You

1st Generation Pedigree

• Sire: Improbable
  Improbable, a Grade 1 winner by City Zip, won the 2020 Hollywood Gold Cup (G1), Awesome Again Stakes (G1), and Whitney Stakes (G1). Standing at WinStar Farm for $15,000 in 2025, he has sired promising runners like Pay Billy, who inherit his blend of speed and middle-distance stamina. Improbable’s success at 1 1/8 to 1 1/4 miles, including a second in the 2019 Preakness, makes him a key influence for Pay Billy’s Preakness prospects.
• Dam: Harlington’s Rose
  Harlington’s Rose, by Harlington, was a stakes-placed mare who earned $420,772, winning at distances up to 1 1/16 miles and placing in the 2014 La Canada Stakes (G2). As a broodmare, she has produced multiple winners, with Pay Billy being her standout foal. Her Harlington lineage adds durability, complementing Improbable’s speed, which supports Pay Billy’s ability to compete in stakes races at 1 to 1 1/8 miles.

2nd Generation Pedigree

• Improbable’s Parents (Pay Billy’s Paternal Grandparents)
  Improbable’s sire is City Zip, a Grade 1 winner by Carson City who won the 2000 Hopeful Stakes (G1) and became a leading sire, producing Collected (2017 Pacific Classic) and Dayatthespa (2014 Breeders’ Cup Filly & Mare Turf). City Zip’s progeny excel at 6 furlongs to 1 1/8 miles, providing Pay Billy with tactical speed. Improbable’s dam is Rare Event, by A.P. Indy, an unplaced mare whose family includes Grade 1 winner Point of Entry. Rare Event’s A.P. Indy lineage adds stamina, enhancing Pay Billy’s suitability for the Preakness distance.
• Harlington’s Rose’s Parents (Pay Billy’s Maternal Grandparents)
  Harlington’s Rose’s sire is Harlington, a Tapit son who won at 1 1/8 miles and s personally for me has produced stakes winners like Synchrony (2018 King Edward Stakes). Harlington’s Tapit lineage contributes class and stamina, ideal for middle distances. Harlington’s Rose’s dam is A Rose For You, by Orientate, a winning mare who earned $93,688 and won at 6 furlongs. A Rose For You is a half-sister to stakes-placed runners, and her Orientate lineage adds speed, balancing Harlington’s stamina for Pay Billy’s versatile running style.

Additional Notes on Pay Billy’s Pedigree

• Paternal Line (Improbable): Improbable’s sire, City Zip, and grandsire, Carson City, provide a foundation of speed, with Carson City siring sprinters like City Zip and Five Star Day. Rare Event’s A.P. Indy lineage, with A.P. Indy’s 1992 Belmont Stakes win, adds classic stamina, as seen in Improbable’s Grade 1 wins at 1 1/4 miles. This line supports Pay Billy’s front-running style, evident in his Federico Tesio Stakes win (1:52.57).
• Maternal Line (Harlington’s Rose): Harlington, Harlington’s Rose’s sire, brings Tapit’s class, with Tapit siring four Belmont Stakes winners, including Tonalist (2014). Harlington’s Rose’s dam, A Rose For You, by Orientate, contributes speed through Orientate’s 2002 Breeders’ Cup Sprint win. Harlington’s Rose herself was a durable runner, competing in 24 races and placing in graded stakes, which supports Pay Billy’s consistency (6 of 8 in the money). The Improbable-Harlington cross combines City Zip’s speed with Tapit’s stamina, aligning with Pay Billy’s 4-for-8 record and stakes success at 1 1/16 to 1 1/8 miles.
• Pedigree Fit for the Preakness: Pay Billy’s 4-for-8 record, with three stakes wins in 2025 (Federico Tesio, Private Terms, Miracle Wood), and a 93 speed figure in his latest victory demonstrate his readiness for the 1 3/16-mile Preakness. His sire Improbable’s Preakness experience and Harlington’s Tapit lineage provide stamina, while City Zip’s influence ensures tactical speed. Pay Billy’s front-running style, as seen in his rail-hugging Tesio win, suits Pimlico’s tight turns, and his recent workouts (e.g., 4 furlongs in :49.00 at Delaware Park on May 8, 2025) indicate peak form.

Pay Billy’s Race Record

Notes:

• Career Record: 4 wins, 1 second, 1 third in 8 starts.
• Career Earnings: $234,475.
• Running Style: Front-runner with tactical speed, capable of leading from the start or pressing the pace, as shown in his Federico Tesio and Private Terms Stakes wins.
• Pay Billy debuted in September 2024, finishing off the board in his first two starts but broke his maiden decisively on December 15, 2024, at 6 furlongs. In 2025, he won three stakes races at Laurel Park, including the Federico Tesio Stakes by a head after a stretch duel, and showed versatility by rallying from second in the Miracle Wood Stakes. His consistent improvement and stakes success make him a live longshot for the Preakness.