By Mint Julep


Harry Payne Whitney Trainer: Two Kentucky Derby Winners

1915 kentucky derby winner regret

Key Takeaways

  • Harry Payne Whitney, a member of a wealthy and influential family, left his mark on Thoroughbred horse racing by excelling as both a breeder and owner.
  • Whitney stood out in the racing scene for owning two Kentucky Derby winners – Regret in 1915 and Whiskery in 1927. This showcased his talent in selecting top-notch horses with excellent breeding potential.
  • Besides achieving success on the racetrack, Whitney’s impact is felt internationally through accolades such as being honored at the Hall of Fame. His philanthropic work also continues to shape today’s world of Thoroughbred horse racing.

Early Life and Family Background

Harry Payne Whitney, born on April 29, 1872 in the bustling heart of New York City, was set for greatness from day one. Being the first child of Flora Payne and William C. Whitney meant he inherited a name steeped in history and a legacy rooted deeply in business and politics.

Growing up surrounded by luxury and privilege, young Harry immersed himself in a world where success felt like second nature. When his father passed away, Harry inherited an immense fortune that opened doors to leave an unforgettable mark across various fields far beyond anyone’s expectations.

As he entered adulthood, it became evident that Harry wasn’t content with just coasting on his family’s wealth or reputation. He had a drive and ambition that separated him from others of similar background—a fiery determination to carve out his own path in the world.

Year after year, Harry Payne Whitney’s renown continued to rise—not only among elite social circles but also among those who admired his work ethic and resolve. His journey stands as inspiration for all dreamers who dare to think big and strive relentlessly toward their goals against all odds.

Introduction to Racing

Harry Payne Whitney, a man with a wide range of interests in sports and business, delved into the world of thoroughbred horse racing after finding success in polo and yacht racing. Transitioning from his academic pursuits to follow his love for sports displayed his strong determination and adaptability.

Whitney shook up the horse racing scene with his sharp breeding strategies, leading him to own two Kentucky Derby champions. His keen eye for picking top bloodlines and nurturing young talent made him stand out as a significant figure in the sport.

His influence extended beyond borders through participation in international races, where his horses not only excelled on American tracks but also left their mark on prestigious events worldwide. This solidified Whitney’s reputation as a powerful force in the equestrian realm.

Whitney’s unwavering dedication to horse racing earned him recognition when he was inducted into the Racing Hall of Fame. This honor celebrated not just his victories on racetracks but also underscored his lasting legacy as a breeder and owner who influenced Thoroughbred history significantly.

Apart from making an impact on horse racing, Harry Payne Whitney’s philanthropic efforts endeared him to many outside the sporting community. With great generosity rivaled by few, he used his resources to support various charitable causes that uplifted communities far beyond racetracks—a testament both to his sporting abilities and compassionate nature.

The Pros & Cons of Racing Legacy


  1. Having a family or individual with a strong history in racing can elevate their status and lead to increased respect.
  2. It helps foster a feeling of tradition and ongoing connection within the racing world.
  3. A notable racing legacy has the potential to draw in sponsors, investors, and chances for partnerships.
  4. The expertise and wisdom handed down through generations play a key role in sustaining success within the field.


  1. A family’s history in racing can put a lot of pressure on someone to match the achievements of their ancestors.
  2. This might make it hard for them to be recognized for what they achieve as an individual, with everyone always comparing them to those who came before.
  3. When success is handed down through generations, it could lead to feeling too comfortable or not having enough drive to set new goals and strive for personal growth.
  4. Arguments within the family about how to handle the racing legacy could cause tension, affecting relationships and business decisions.

Triple Crown Triumphs

Harry Payne Whitney was a standout breeder and owner in the world of Thoroughbred horse racing, achieving impressive victories at the renowned Kentucky Derby. The win by Regret in 1915 not only made her the first filly to triumph in this historic race but also established Whitney as a formidable presence on the racetrack. Nearly ten years later, Whiskery raced to victory for Whitney in 1927, showcasing his ongoing pursuit of excellence and success.

Apart from his notable successes at the Kentucky Derby, Harry Payne Whitney’s horses dominated other prestigious races like the Preakness Stakes and Belmont Stakes. These wins highlighted Whitney’s firm commitment to breeding and owning top-notch Thoroughbreds that excelled on some of horse racing’s biggest platforms. Each triumph demonstrated both his ability to spot talent and his strategic approach to developing champions who could outshine their rivals with skill and agility.

As these victories echoed throughout the horse racing community, Harry Payne Whitney solidified himself as more than just a successful breeder and owner; he became a prominent figure whose influence transcended borders. His legacy extended far beyond American shores, leaving an enduring mark on international horseracing circles. It came as no surprise when he was posthumously honored with induction into the National Museum of Racing Hall of Fame, securing his position among legends whose contributions continue shaping equestrian sports today with significant impact.

Major Stakes Wins

Whitney’s horse farm in Lexington, Kentucky bred many winning horses that triumphed in high-stakes races like Equipoise and Johren. His horses won prestigious events, showcasing his skills as a breeder and owner in the racing world.

The peak of Whitney’s remarkable career arrived when he was rightfully honored with induction into the National Museum of Racing and Hall of Fame. This recognition celebrated his impactful contributions to the sport through his outstanding achievements both as a breeder and an owner.

Key Life Events and Achievements

Information Details
Born April 29, 1872
New York City, U.S.
Died October 26, 1930 (aged 58)
Portland, Maine, U.S.
Resting place Woodlawn Cemetery,
The Bronx, New York
Education Groton School
Alma mater Yale University
Columbia Law School
Occupation(s) Businessman, racehorse owner/breeder, philanthropist
Political party Democratic
Board member of Long Island Motor Parkway
Hudson Bay Mining & Smelting Co.
Spouse Gertrude Vanderbilt (m. 1896)
Children Flora, Cornelius, and Barbara
Parent(s) William Collins Whitney
Flora Payne
Family Whitney
Honors Pillars of the Turf (2018)
U.S. Polo Hall of Fame (1990)

International Success

Harry Payne Whitney was a major player in the world of Thoroughbred horse racing, making a name for himself not just in America but around the globe. His horses were superstars on an international level, proving him to be an exceptional breeder and owner of top-notch equine athletes.

Whitney’s bloodlines showed their strength across different countries, with his horses consistently dominating prestigious races worldwide. Their wins captured the attention of audiences everywhere, establishing Whitney as a forward-thinking leader in the sport.

From England to France, Harry Payne Whitney made waves at some of the most famous racing events, leaving behind a lasting impact on Thoroughbred horse racing history. His talent for producing champions that excelled both at home and abroad highlighted his unmatched expertise and commitment to excellence.

Hall of Fame Induction

Harry Payne Whitney was recognized for his significant contributions to Thoroughbred horse racing after his passing. In 2018, he was voted as one of the Pillars of the Turf by the National Museum of Racing and Hall of Fame, and also inducted into the U.S Polo Hall of Fame. Whitney’s breeding program was top-notch, going beyond just winning the Kentucky Derby. His horses were known for their success both nationally and internationally, clinching major stakes wins that solidified his reputation as a skilled owner-breeder.

Whitney made a big impact on Thoroughbred horse racing worldwide; he wasn’t just famous locally but had influence globally in the sport. With an eye for exceptional bloodlines and a strong commitment to excellence, Whitney set a high standard felt throughout the industry. His horses weren’t just participants; they were dominant forces on racetracks from America to Europe with unmatched grace and speed.

Though faced with challenges and setbacks along the way, Harry Payne Whitney overcame them through perseverance and sheer determination, turning obstacles into stepping stones towards greatness. Each win at prestigious races like Belmont Stakes or Saratoga Race Course not only added shiny trophies to his collection but also entrenched him deeper into racing history.

Aside from triumphs on track, Harry Payne Whitney left behind a lasting legacy through philanthropy and stewardship within equestrian circles. By ensuring equine heritage preservation and supporting young talent, he paved the way for future generations to benefit from his wisdom long after his time passed away. In many ways, Whitney’s legacy acts as guidance for aspiring breeders and owners aiming not only for success but also longevity in this esteemed sport.

Being inducted into halls of fame isn’t solely about acknowledging accomplishments; it’s about immortalizing legends whose impact spans across generations. For Harry Payne Whitney entering these revered halls represents more than personal achievement—it stands as evidence of lifelong dedication toward elevating Thoroughbred horse racing into an art form appreciated by enthusiasts all over.

Legendary Stories Surrounding Derby Champion Trainers

  1. Legendary Tales of Derby Champion Trainers: Harry Payne Whitney Trainer – Two Victorious Kentucky Derby Colts
  2. Family Tradition: Harry Payne Whitney, a notable American entrepreneur and thoroughbred horse breeder, had strong ties to the world of horse racing thanks to his grandfather, William Collins Whitney. The family’s successful history in owning and breeding racehorses sparked Harry’s passion for the sport from an early age.
  3. Regrettable Choice: In 1915, Harry Payne Whitney made a controversial move by selling off his prized colt, Regret – who later went on to become the first filly ever to win the prestigious Kentucky Derby title. Reflecting back on this decision later on, he expressed deep regret as it meant missing out on having a winning Derby horse in his own stable.
  4. Maiden Derby Victory: Despite the disappointment over letting go of Regret, Harry Payne Whitney clinched his inaugural triumph at the Kentucky Derby as a trainer in 1927 with Whiskery – an impressive colt under his guidance. This victory marked just the beginning of what would be known as Whitney’s esteemed legacy within horseracing circles.
  5. Second Triumph at The Derby: A few years later in 1931 came yet another glory for Whitney when Twenty Grand surged ahead to claim victory at the prestigious Kentucky Derby event under both training by him and skilled riding by jockey Charley Kurtsinger. Twenty Grand’s dominating performance solidified Whitneys’ reputation as not only a seasoned trainer but also one capable of producing top-tier racehorses.
  6. Enduring Impact: Beyond being recognized for successes in breeding and training horses, Harry Payne Whitneys’ dedication and pursuit of excellence have left an enduring mark within horseracing communities worldwide inspiring future generations including trainers like yourself! His commitment continues shaping perspectives among owners and enthusiasts alike ensuring that his remarkable legacy lives vibrantly within every chapter penned down across derby history till date!


Harry Payne Whitney didn’t just focus on horse racing – he also supported scientific research in a big way. One of his major contributions was funding the Whitney South Seas Expedition, led by Rollo Beck, which made significant strides in botanical studies during its time.

Besides his success in horse racing, Harry Payne Whitney used his wealth and influence to make important impacts across different fields. For example, he generously funded expeditions that helped advance scientific exploration, such as the well-known Whitney South Seas Expedition under Rollo Beck’s guidance.

Whitney’s legacy goes beyond just horse racing; it includes significant achievements in areas like scientific discovery and philanthropy. His support for projects like the groundbreaking Whitney South Seas Expedition with Rollo Beck at the helm played a crucial role in advancing botanical knowledge during their era.

In addition to excelling on racetracks with champion horses, Harry Payne Whitney had a lasting impact through his commitment to supporting valuable scientific initiatives. By financing ambitious projects like the renowned Whitneysouthseas Expedition led by Rollo beck; he contributed to advancements in botanical studies still recognized today.

Personal Life and Legacy

Harry Payne Whitney, who was married to Gertrude Vanderbilt from the famous Vanderbilt family, had three children – Flora Payne Whitney, Cornelius Vanderbilt Whitney, and Barbara Vanderbilt Whitney. He continued his family’s legacy both in horse racing and beyond. His impact on Thoroughbred horse racing is still felt today because of his successful breeding program that not only shaped American polo ponies but also produced champion racehorses that left a lasting mark on the sport.

Whitney showed his skills as a breeder through two standout horses: Regret and Whisk Broom II. In 1915, Regret made history by becoming the first filly to win the Kentucky Derby under Harry’s ownership. This victory not only showcased her talent but also highlighted Harry’s ability to choose top-quality bloodlines. Meanwhile, Whisk Broom II achieved success in multiple prestigious races such as the Metropolitan Handicap and Brooklyn Handicap during an impressive career that solidified Harry’s reputation as a breeder of champions.

Harry Payne Whitney expanded his influence internationally by acquiring French-bred stallions which improved the quality of American Thoroughbreds. This strategic decision raised American racing standards while strengthening connections between European and US breeding programs. By incorporating diverse bloodlines into his breeding stock, he played a crucial role in shaping modern pedigrees worldwide.

In honor of his remarkable achievements within horseracing circles, Harry Payne Whitney was posthumously inducted into the National Museum of Racing Hall of Fame in 1955 for leaving an enduring legacy through generations of exceptional racehorses descended from those bred under him – showcasing his lasting impact on equestrian excellence globally.

Outside horseracing pursuits, Harry Payne Whitney engaged in philanthropic efforts showing dedication towards making meaningful contributions beyond sports arenas.. From supporting various charitable causes to investing in art collections later forming part of renowned museums like The Met Cloisters – it is evident that he viewed success not just measured by wins at racetracks but by enriching society through cultural preservation efforts.


1. What were the names of the two Kentucky Derby champions owned by Harry Payne Whitney?

In 1915, Harry Payne Whitney was the proud owner of the Kentucky Derby champion Regret and repeated his success in 1927 with Whiskery.

2. How did Harry Payne Whitney’s breeding program contribute to his success in Thoroughbred horse racing?

Harry Payne Whitney carefully bred horses by combining the best bloodlines and choosing exceptional broodmares. This process helped him create champions like Regret and Whisk Broom II, establishing his reputation as a key figure in Thoroughbred horse racing.

3. What other major stakes races did Harry Payne Whitney’s horses win besides the Kentucky Derby?

Harry Payne Whitney won the Kentucky Derby with Regret in 1915 and Whiskery in 1927. His horses also conquered top races like the Belmont Stakes, Preakness Stakes, and Travers Stakes. This success made him a key figure in Thoroughbred horse racing history.

4. How did Harry Payne Whitney’s impact on horse racing extend beyond the United States?

Harry Payne Whitney not only influenced horse racing in the United States but also made a mark internationally with his breeding program. By producing champions in Europe, he established himself as a dominant figure in the sport worldwide.

5. What led to Harry Payne Whitney’s induction into the National Museum of Racing and Hall of Fame?

Harry Payne Whitney earned his spot in the National Museum of Racing and Hall of Fame because he was an outstanding breeder and owner. He had two Kentucky Derby champions, Regret and Whisk Broom II, as well as many other big wins in important races. His influence on Thoroughbred horse racing was huge.

6. In what ways did Harry Payne Whitney use his wealth and influence for philanthropic endeavors related to horse racing and beyond?

Harry Payne Whitney actively used his wealth and influence to back a range of philanthropic projects connected to horse racing. He financed the building of the Belmont Park racetrack and also donated to charitable causes like hospitals, universities, and the arts.