By Mint Julep

Kentucky Derby Winner Twenty Grand 1931

kentucky derby winner twenty grand 1931

In 1931, the Kentucky Derby witnessed a historical victory as Twenty Grand, owned and bred by the prestigious Greentree Stable of Helen Hay Whitney, emerged triumphant. This exceptional race marked a significant moment in horse racing history due to Twenty Grand’s outstanding performance. The unique ownership and breeding legacy that distinguished Twenty Grand are worth exploring further in this narrative. Key figures such as owner Helen Hay Whitney, jockey Charley Kurtsinger, and trainer James G. Rowe Jr., all played crucial roles in securing the triumph of Twenty Grand at Churchill Downs during this unforgettable event back in time.

Kentucky Derby Winner Twenty Grand 1931

The 1931 Kentucky Derby was the 57th edition of the prestigious horse race, a historic event that will always be remembered in books for its remarkable winner, Twenty Grand. This majestic colt, owned and bred by Helen Hay Whitney’s Greentree Stable, captured everyone’s attention with his outstanding victory. Guided by the spirited jockey Charley Kurtsinger, Twenty Grand showcased a perfect mix of skill and determination that left fans in awe.

This triumph wasn’t just about winning; it symbolized years of careful breeding and training under James G. Rowe Jr.’s expert guidance. With an impressive finishing time of 2:01.80, this dynamic duo broke previous records at Churchill Downs on that memorable day, proving their dominance without question. It was more than a race; it embodied perseverance, passion, and unwavering dedication to the sport.

As Twenty Grand raced towards victory at the 1931 Kentucky Derby, he carried not only speed and strength but also the hopes and dreams of all those who had supported him along his journey. The thunderous sound of hooves challenging tradition echoed through time as spectators watched history being made before their eyes. In that monumental win lay not just fame but also a powerful reminder that greatness has no limits when talent seizes opportunities on racing’s biggest stage.

Precedence in Racing Schedule

The 1931 Kentucky Derby had an interesting twist – it came right after the Preakness Stakes, which was held a week earlier on May 9. This was pretty rare since usually, the Kentucky Derby takes place before the Preakness.

Moreover, until races were rescheduled in 2020 due to COVID-19, this event was one of those few times when the Kentucky Derby wasn’t set as the first race of the Triple Crown initially.

The Pros & Cons of Racing Legends


  1. Racing enthusiasts are amazed and inspired by the skill and talent displayed by both horses and jockeys.

  2. Spectators experience a thrilling and exciting time at horse races.

  3. Horse racing showcases its rich history and tradition.

  4. Valuable lessons in perseverance, determination, and sportsmanship are offered through the sport.


  1. Racing can cause injuries or accidents for both horses and riders

  2. Racing may continue to raise animal welfare concerns in the industry

  3. Sometimes intense competition overshadows true sportsmanship

  4. High stakes in races can pressure fair play

  5. Focusing on winning might distract from enjoying the beauty and grace of the sport

Full Results and Payouts

In the race results, jockey Charley Kurtsinger rode Twenty Grand to a thrilling victory. Sweep All came in second place, with Mate finishing third. Twenty Grand earned an impressive $48,725 prize money and also received a $5,000 Gold Cup for clinching first place. The other horses that placed were awarded varying amounts for their positions from second to fourth.

The 1931 Kentucky Derby witnessed an outstanding display of talent by the iconic horse Twenty Grand. Owned by Helen Hay Whitney and trained by James G. Rowe Jr., this exceptional horse demonstrated unmatched skill on the track that day. With Charley Kurtsinger expertly guiding him through the competition, Twenty Grand made history as one of Churchill Downs’ most celebrated champions.

Twenty Grand’s victory went beyond just winning a prestigious race; it symbolized a legacy of excellence in breeding and horseracing expertise. The combination of Whitney’s focus on top-tier bloodlines, Rowe’s years of training experience dedicated to the sport, and Kurtsinger’s superb riding abilities resulted in an unforgettable triumph at the 1931 Kentucky Derby. This win set a benchmark that would be remembered for generations—a testament to how passion and dedication can shape sporting greatness.

Impactful Breeding Legacy

In 1931, Twenty Grand made an impressive win at the Kentucky Derby thanks to Greentree Stable’s strong breeding legacy. The horse was owned by Helen Hay Whitney and had been bred for success, living up to its pedigree with a fantastic victory at Churchill Downs. With Whitney’s foresight and trainer James G. Rowe Jr.’s expertise, Twenty Grand showed remarkable speed and stamina on the race day.

This triumph not only secured Twenty Grand’s place in racing history but also showcased the important connections between key individuals involved in his victory. Jockey Charley Kurtsinger played a crucial role in guiding Twenty Grand to glory by displaying exceptional skill during their standout performance at the Kentucky Derby. The teamwork among Kurtsinger, Rowe Jr., and Whitney demonstrated how dedication can lead to achieving extraordinary results in horse racing.

The 1931 Kentucky Derby win of Twenty Grand is a great example of how careful breeding practices combined with expert training can produce champions capable of making a lasting impact on the sport. This significant event not only reflected Greentree Stable’s commitment to excellence but also emphasized their enduring influence on shaping future generations of top-notch racehorses destined for success worldwide

1931 Kentucky Derby Top Finishers Snapshot

Finished Post Horse Jockey Trainer Owner Time / behind
1st 5 Twenty Grand Charley Kurtsinger James G. Rowe Jr. Greentree Stable 2:01.80
2nd 1 Sweep All Frank Coltiletti Clyde Van Dusen Dixiana 4
3rd 10 Mate George Ellis James W. Healy Albert C. Bostwick Jr. 1
4th 6 Spanish Play Charles E. Allen George Land Knebelkamp & Morris 4
5th 7 Boys Howdy Gilbert Riley Loyd Gentry Sr. Harry C. Hatch 1+1/2
6th 12 Insco Steve O’Donnell Charles E. Durnell Griffin Watkins 6
7th 9 Pittsburgher Charles Corbett James H. Moody Shady Brook Farm Stable 1
8th 3 The Mongol James McCoy William Reed Hamburg Place Head
9th 4 Ladder Louis Schaefer Jack R. Price Walter J. Salmon Sr. 1
10th 2 Anchors Aweigh Earl Steffen James G. Rowe Jr. Greentree Stable Head
11th 8 Surf Board Clarence Watters James G. Rowe Jr. Greentree Stable 2
12th 11 Prince d’Amour Eugene James Nathaniel K. Beal Joseph Leiter 8

Uniqueness in Owner-breeder Dual Role

In the 1931 Kentucky Derby, Helen Hay Whitney’s Greentree Stable achieved a remarkable feat with Twenty Grand. This victory showcased an exceptional combination of ownership and breeding expertise in horse racing history. Helen Hay Whitney was a prominent figure known for her ability to breed top-tier racehorses and courageously enter them into prestigious events like the Kentucky Derby. She played a dual role that highlighted her deep involvement in various aspects of horse racing, from nurturing bloodlines to owning successful contenders at esteemed races like the Kentucky Derby.

Twenty Grand’s win wasn’t just another triumph at Churchill Downs; it demonstrated how meticulous planning, expert training, and exceptional talent could converge on one glorious day in May. Under the guidance of renowned trainer James G. Rowe Jr., Twenty Grand entered the starting gate ready to showcase his skills and meet high expectations.

Adding to this winning team was jockey Charley Kurtsinger who rode Twenty Grand with skill and finesse that seemed destined for greatness. Kurtsinger’s adept handling of Twenty Grand around the track solidified their partnership as they surged past their competitors towards victory.

As they raced down the homestretch amid cheers echoing through Churchill Downs, it wasn’t just a horse crossing the finish line; it was history galloping forward on four powerful hooves. The legacy created by Twenty Grand’s triumph went beyond mere statistics—it became a symbol of dedication, passion, and unwavering belief against all odds.

Looking back at that historic day in 1931 when owner-breeder roles seamlessly merged under Whitney’s leadership—producing champions like Twenty Grand—we see more than just a race won; we witness an inspiring tale of perseverance, excellence, and determination resonating through time itself.

Noteworthy Time Record Set

When Twenty Grand won the Kentucky Derby in 1931, he set a new record time that stood out in derby history for many years. Other competitors eventually broke or equaled his records later on. This amazing achievement highlighted Twenty Grand’s exceptional speed and endurance, solidifying his place as a true champion in horse racing history.

As Twenty Grand thundered across the finish line, joining legendary horses, it marked an unforgettable moment in the sport. Spectators cheered and applauded as they witnessed this incredible feat unfold before their eyes. It was clear that Twenty Grand had surpassed mere competition to become one of racing’s greats.

The sound of hooves pounding against the turf echoed through Churchill Downs, symbolizing triumph over tough odds. In that split second captured forever, jockey Charley Kurtsinger expertly guided Twenty Grand towards glory with skill and determination.

Amidst all the celebrations and praise showered upon them both, owner Helen Hay Whitney watched proudly from afar. Her vision combined with trainer James G. Rowe Jr.’s expertise led Twenty Grand towards greatness where champions are remembered for eternity.

Breaking records was not just about numbers; it was rewriting narratives woven into racing lore—a tale where perseverance met pedigree under bluegrass skies filled with dreams galloping towards unseen horizons.

The Mystique Surrounding a Champion's Victory

  1. ### The Fascination Surrounding a Champion's Triumph

  2. **Unbeaten Streak**: Back in 1931, Twenty Grand emerged victorious at the Kentucky Derby with an impressive record of 11 wins out of 15 races throughout his career. This outstanding feat firmly established him as a true champion within the realm of horse racing.

  3. **Legendary Lineage**: Sired by the renowned stallion St. Germans, Twenty Grand boasted a prestigious bloodline known for producing exceptional racehorses. His impressive family background added to the allure surrounding his triumph at the Kentucky Derby and secured his place in racing lore.

  4. **Memorable Comeback**: Despite encountering setbacks and injuries earlier on, Twenty Grand staged a remarkable comeback to clinch victory at the 1931 Kentucky Derby. His triumphant return to the track captivated audiences, showcasing both his resilience and unwavering determination as a champion.

  5. **Historic Winning Margin**: The memory of Twenty Grand’s win at the 1931 Kentucky Derby remains etched due to his remarkable eight-length lead over his closest rival upon crossing the finish line – solidifying his supremacy and leaving spectators awestruck.

  6. **Everlasting Impact**: Decades following his historic triumph at Churchill Downs, Twenty Grand’s legacy continues to captivate fans and enthusiasts in horse racing circles alike.. His tale stands as an enduring testament to perseverance, skill, and dedication required for achieving greatness in this sport; thus making him an iconic symbol of excellence among champions that transcends time barriers.

Jockey Charles Kurtsinger’s Triumph

At Churchill Downs, where the crowd roared and horses thundered past, Charles Kurtsinger’s bond with Twenty Grand was unmistakable. The way he expertly guided the spirited colt during the 1931 Kentucky Derby left everyone in awe. His precise timing and strategic moves led Twenty Grand to a historic win that would be remembered for years.

Kurtsinger’s connection with Twenty Grand wasn’t just about skill; it was like watching a perfect dance between man and horse on the track. They moved as one, responding intuitively to each other’s signals. This incredible teamwork propelled them ahead of their rivals with grace and determination, resulting in an impressive victory at one of America’s most prestigious races.

As they raced towards victory that unforgettable day, Kurtsinger must have felt an exhilarating rush unlike anything else. Navigating Twenty Grand through those heart-pounding moments demanded nerves of steel and unwavering focus – traits that set him apart as a top jockey in a competitive era filled with talent. His sharp decision-making under pressure further solidified his reputation as an exceptional rider.

The partnership between Kurtsinger and Twenty Grand went beyond just sports; it showcased trust, dedication, and sheer passion for winning races! Their seamless communication on the racetrack spoke volumes about their mutual respect and admiration for each other’s skills. Together, they painted an unforgettable picture of outstanding teamwork amid cheers from devoted fans who witnessed greatness unfold before their eyes.

Looking back at Charles Kurtsinger’s triumph aboard Twenty Grand isn’t merely about winning a race—it represents perseverance against all odds, self-belief when others doubt you, seizing opportunities when they arise. It stands as a lasting reminder that success is not only reaching the finish line first but also creating unbreakable bonds that transcend time—a legacy immortalized by their legendary victory at Churchill Downs in 1931.

Trainer James G. Rowe Jr.’s Expertise

Trainer James G. Rowe Jr. guided Twenty Grand to victory at the prestigious 1931 Kentucky Derby, showcasing peak performance under his expert care. This win wasn’t just luck – it was a testament to Rowe’s meticulous training tailored to each horse’s needs.

Rowe’s mastery shone through in every detail of Twenty Grand’s race prep – from diet plans to exercise routines, he left no stone unturned. His unwavering commitment to excellence distinguished him as one of the top trainers of his time. The powerful connection between trainer and horse drove Twenty Grand towards success on that memorable day at Churchill Downs.

The winning trio of owner Helen Hay Whitney, jockey Charley Kurtsinger, and Trainer James G. Rowe Jr., formed an unbeatable team that propelled Twenty Grand to triumph at Churchill Downs. Each played a vital role in shaping the champion – Whitney with her vision, Kurtsinger guiding on the track, and Rowe using his expertise behind-the-scenes seamlessly combined for racing history.

Twenty Grand’s impact extended beyond victories; it represented perseverance against all odds and showcased how passion paired with skill can lead to remarkable accomplishments in any field. In an era where horse racing reigned supreme as America’s favorite pastime, Twenty Grand stood out not only for speed but also for embodying unity among believers – a true champion both on and off the racetrack.


1. What made Twenty Grand's victory at the 1931 Kentucky Derby particularly significant in horse racing history?

The 1931 Kentucky Derby win by Twenty Grand made a huge impact in horse racing history. This victory was remarkable because of his outstanding lineage, being owned by the respected Helen Hay Whitney, and he set a new track record that remained unbeaten for more than twenty years.

2. How did owner Helen Hay Whitney's background and legacy contribute to the success of Twenty Grand?

Helen Hay Whitney, a well-known socialite and descendant from a prestigious family, significantly influenced Twenty Grand's triumph by offering the horse exceptional care, training, and genetic potential.

3. Who was the jockey that rode Twenty Grand to victory at the 1931 Kentucky Derby, and what was their role in this historic win?

In 1931, Jockey Charley Kurtsinger skillfully rode Twenty Grand to win the prestigious Kentucky Derby. Their remarkable teamwork and talent led to a historic victory that captured the hearts of many.

4. Can you elaborate on the breeding lineage of Twenty Grand and how it played a part in his success on the racetrack?

Twenty Grand came from a prestigious line of ancestors, including the famous horses Man o' War and War Admiral. This lineage gave him a winning combination of speed and endurance that helped him win the Kentucky Derby in 1931.

5. What distinguished trainer James G. Rowe Jr.'s approach in preparing Twenty Grand for the Kentucky Derby, and how did it impact the outcome of the race?

Trainer James G. Rowe Jr. paid close attention to every detail and focused on getting Twenty Grand in top shape for the Kentucky Derby. He really understood what Twenty Grand could do, which helped them win the race in 1931.

6. In what ways did Twenty Grand's record-setting performance at the 1931 Kentucky Derby influence future generations of racehorses and shape the sport of horse racing?

Twenty Grand made history at the 1931 Kentucky Derby with his record-breaking performance. His win not only established him as a legendary racehorse but also motivated upcoming horses to strive for greatness. This victory highlighted the importance of top-notch breeding, ownership, and training in achieving unparalleled success on the racetrack, leaving a lasting impact on the sport.