By Mint Julep


Charley Kurtsinger Jockey: Two Kentucky Derby Wins

kentucky derby winner twenty grand 1931

Join us on an exciting journey as we dive into the remarkable career of Charles Kurtsinger, a renowned jockey celebrated for his exceptional skills in horse racing. Starting from his early days, where he learned the ropes from experienced riders, to his historic wins riding Twenty Grand and War Admiral at the Kentucky Derby – witness Kurtsinger’s strategic brilliance and unparalleled talent that propelled him to the peak of success in the racing world. Discover his enduring legacy filled with prestigious awards, iconic match races, and unwavering commitment to a sport that continues to inspire racing fans around the globe.

Early Life and Racing Beginnings

Charles Kurtsinger was born on November 16, 1906, into a family that adored horse racing. His father was a jockey and Charles grew up learning everything about the sport from him. He also had Mack Garner as his mentor, who taught him all about race riding. Even at a young age when most kids were still figuring out life, Charles dived headfirst into the exciting world of horse racing.

By the time he turned 21 years old—the legal drinking age for many—Kurtsinger was already making headlines in races that caught everyone’s attention. Winning the Oakdale Handicap and Bay Shore Handicap wasn’t just luck; it showed that he belonged with the best riders out there. People who truly understood horseracing saw these victories as glimpses of greatness in the making.

When Charles rode powerful horses on tracks across America, his confidence shone through every stride he took alongside them. The bond between man and mount was strong because they spent countless hours together training. Kurtsinger didn’t just ride horses; he worked like an artist creating masterpieces with each gallop over turf canvases.

In a time where skill mattered more than flashy displays alone, Charles stood out not only for his agility but also for his smart moves on racetracks that were like chessboards waiting to be conquered by skilled players. Every choice he made during races wasn’t impulsive but carefully planned steps taken amidst thundering hooves pounding rhythmically below like music celebrating pure speed itself.

As Kurtsinger raced across different courses nationwide—from Churchill Downs to Belmont Park—it became clear that he wasn’t chasing victory; destiny itself seemed to run towards him at incredible speeds known only to those brave enough to face fate head-on with unwavering determination etched deeply within their being.

Kentucky Derby Wins with Twenty Grand

In 1931, at the lively Churchill Downs, Charles Kurtsinger and Twenty Grand made history with their impressive speed and skill. The duo’s perfect teamwork captured everyone’s attention as they raced ahead to win the famous roses at the Kentucky Derby. Kurtsinger expertly guided Twenty Grand, leaving spectators amazed and establishing himself as an exceptional jockey.

The victory on Twenty Grand not only secured Kurtsinger a place in horse racing history but also paved the way for his successful career to continue flourishing. As they crossed the finish line together flawlessly, it was clear that Kurtsinger had a natural connection with his horse, enabling them to move in perfect harmony. This partnership between man and horse drove them to triumph over tough competition, showcasing their remarkable abilities.

With grace and determination evident at every step, Charles Kurtsinger rode Twenty Grand like a work of art towards another victory at Churchill Downs in 1936. The second Kentucky Derby win confirmed Kurtinger’s reputation as a masterful rider on Thoroughbreds—his legacy forever linked with stories of bravery under pressure and elegance on the racetrack.

The Pros & Cons of Jockeying Success


  1. Work closely with magnificent horses
  2. Potential to gain fame and recognition in the world of horse racing
  3. Thrilling and adrenaline-pumping career opportunities
  4. Opportunities to compete in prestigious events such as the Kentucky Derby
  5. Possibility of earning substantial prize money
  6. Forming strong relationships with trainers, owners, and fellow jockeys


  1. Racing involves a high risk of getting hurt from falls or accidents.
  2. It requires a lot of physical effort and you have to meet specific weight standards.
  3. Job stability is uncertain as success can vary.
  4. You’ll be traveling often and spending time away from loved ones.
  5. There’s pressure to do well in important races.
  6. The competitive atmosphere can cause stress and exhaustion.

Triple Crown Triumph with War Admiral

In the world of horse racing history, Charles Kurtsinger’s famous ride on War Admiral during the U.S. Triple Crown in 1937 is a shining example of top-notch horsemanship. With each gallop, Kurtsinger and War Admiral moved gracefully towards victory, impressing everyone with their perfect teamwork on the track.

The powerful sound of War Admiral’s hooves echoed through time as Charles Kurtsinger skillfully steered him to success at Churchill Downs, Pimlico Race Course, and Belmont Park. At the Kentucky Derby, spectators marveled at how expertly Kurtsinger led his horse through a crowded field with accuracy and elegance – setting up an unforgettable journey for that year’s Triple Crown competition.

During their final stretch at Belmont Stakes, Kurtsinger’s determination matched by War Admiral’s sheer willpower culminated in a moment of pure glory. Their coordinated movements seemed almost as if they were destined to win – showcasing both jockey and horse achieving perfect unity amidst fierce rivals.

Through his deep love for what he does and strong connection with his equine companion, Charles Kurtsinger embodied what it takes to be a masterful figure in horse racing. His impressive wins in securing the prestigious U.S. Triple Crown alongside War Admiral aren’t just victories; they are timeless achievements crafted on turf where speed meets destiny harmoniously.

Notable Stakes Wins and Earnings

Charles Kurtsinger dominated the racetrack, showcasing his skills in prestigious races like the Lawrence Realization Stakes and Jockey Club Gold Cup. He guided horses to an impressive 721 career wins, establishing himself as one of the top jockeys of his time. Winning the U.S. Champion Jockey titles in 1931 and 1937 based on earnings was not luck but a result of Kurtsinger’s exceptional talent and unwavering dedication to racing.

Kurtsinger’s victories were more than just numbers; they were stories filled with determination, finesse, and sheer grit that captivated audiences. Every win was a masterpiece orchestrated by his expert hands and deep understanding of each horse he rode. Whether dashing towards victory at the finish line or navigating sharp turns, Kurtsinger showed a natural bond with his equine partners that set him apart from other riders. His triumphs echoed through racetracks near and far, cementing his name in racing lore as a master of speed and strategy.

The impact of Charles Kurtsinger’s successes still resonates in horse racing history today, serving as timeless examples of excellence in horsemanship. His legacy goes beyond wins; it inspires generations to pursue greatness while respecting the grace and power of their noble steeds beneath them. Looking back on Kurtsinger’s remarkable career reminds fans that true champions don’t just pursue victory – they embody it every step along the legendary tracks where new heroes are born daily

Legendary Jockey’s Record-Breaking Career Achievements

Attribute Information
Name Charles Kurtsinger
Occupation Jockey
Born November 16, 1906
Shepherdsville, Kentucky, U.S.
Died September 24, 1946 (aged 39)
Louisville, Kentucky
Resting place Saint Michael Cemetery, Louisville, Kentucky
Career wins 721
Major racing wins Oakdale Handicap (1929)
Bay Shore Handicap (1930)
Cowdin Stakes (1930)
Huron Handicap (1930)
Chesapeake Stakes (1931, 1937)
Lawrence Realization Stakes (1931)
Hawthorne Gold Cup Handicap (1931)
Wood Memorial Stakes (1931)
Jockey Club Gold Cup (1931, 1934)
Ladies Handicap (1931, 1937)
Philadelphia Handicap (1931)
Saratoga Handicap (1931, 1938)
Champagne Stakes (1932, 1937)
Great American Stakes (1934)
Saratoga Cup (1934)
Clark Handicap (1936)
Belmont Futurity (1937)
Pimlico Special (1937)
Remsen Stakes (1937)
Wilson Stakes (1938)
Withers Stakes (1938)
U.S. Triple Crown series:
Kentucky Derby (1931, 1937)
Preakness Stakes (1933, 1937)
Belmont Stakes (1931, 1937)
Racing awards U.S. Champion Jockey by earnings (1931, 1937)
Honors United States’ Racing Hall of Fame (1967)
Significant horses Twenty Grand, Head Play, Sun Beau, War Admiral, Menow

Legacy Through Hall of Fame Induction

Charles Kurtsinger, a legendary figure in horse racing, received a posthumous induction into the United States’ Racing Hall of Fame back in 1967. This prestigious honor recognizes his exceptional contributions to the sport and firmly establishes him as one of its most revered icons.

Kurtsinger’s entry into the Racing Hall of Fame shines a spotlight on his incredible career that spanned more than two decades. His outstanding skills and unwavering commitment to horse racing propelled him to legendary status within the industry.

The legacy left by Kurtsinger continues to inspire jockeys today, showcasing not only his prowess on the track but also his character off it. Being inducted into such a respected institution immortalizes not just an individual but an entire era marked by determination, elegance, and excellence in the realm of horse racing.

Iconic Match Race with Seabiscuit

Charles Kurtsinger reached the peak of his successful career when he participated in the famous match race between War Admiral and Seabiscuit. The thrilling event took place at Pimlico Race Course and attracted over 40,000 excited spectators eager to witness history being made in 1938. George Woolf’s skillful handling of Seabiscuit, a horse known for its determination and spirit, demonstrated the jockey’s exceptional talent as he guided the legendary horse towards victory.

The atmosphere was tense as George Woolf  confidently steered Seabiscuit down the final stretch against War Admiral, showing remarkable composure under immense pressure. Despite doubts initially surrounding Seabiscuit’s chances against the strong competitor War Admiral, George Woolf’s strategic moves played a crucial role in achieving an impressive upset win. The crowd erupted with cheers as George Woolf led Seabiscuit across the finish line first, securing his place alongside racing legend forever.

Laura Hillenbrand captured this historic moment vividly in her book “Seabiscuit: An American Legend,” highlighting Charles Kurtsinger’s pivotal role in shaping this unforgettable chapter of horse racing history. The legacy of that iconic match race continues to stand as a tribute to Kurtsinger’s extraordinary talent and unwavering commitment to his profession. Looking back on it now serves as an inspiration not only for fans of horse racing but for anyone who appreciates stories of triumph against all odds.

The Legendary Jockey’s Derby Triumphs Unveiled

  1. ### Revealing the Triumphs of a Legendary Jockey at the Derby
  2. **Starting Out:** Charley Kurtsinger, a jockey hailing from Kentucky, kicked off his professional career in the 1920s when he was just getting started.
  3. **First Victory at the Derby:** Back in 1931, Kurtsinger clinched his inaugural win at the Kentucky Derby while riding Trenty Grand. This achievement marked him as one of the youngest jockeys to conquer this esteemed race during that period.
  4. **Unique Training Approach:** Rumor has it that Kurtsinger had an unconventional training regimen which included sleeping in a coffin to enhance focus and visualize success on the racetrack.
  5. **Second Triumphant Moment:** Fast forward to 1931, where Kurtsinger secured his second triumph at the Kentucky Derby by guiding War Admiral across the finish line – cementing his reputation as a leading jockey of his time.

Transition to Training and Retirement

After retiring from competing in 1939, Charles Kurtsinger smoothly transitioned into training, showcasing his unwavering dedication to the world of horse racing. Despite stepping away from riding, Kurtsinger’s love for horses burned brighter than ever as he immersed himself in coaching and conditioning racehorses.

His shift from jockeying to nurturing future champions highlighted not just his versatility but also his deep affection for these majestic animals. Kurtsinger’s expertise in horse racing became evident in his training techniques, earning him respect and admiration from fellow trainers, owners, and enthusiasts alike.

Guiding young talents towards success on the racetrack, Charles Kurtsinger brought a blend of experience and intuition honed over years at the forefront of competitive racing. His ability to spot promising prospects and enhance their skills underscored his exceptional connection with horses—a skill that distinguished him in an industry where every advantage matters.

Despite later health challenges, Kurtsinger remained committed to shaping the next generation of equine stars. His legacy as both a champion jockey and revered trainer continues to inspire many within the racing community—emphasizing his enduring impact on this storied sport.

Honoring Charles Kurtsinger’s journey from triumphant jockey to esteemed trainer pays tribute not only to him but also captures an era defined by grit, grace, and unyielding passion for all things equestrian. His contributions echo through time; reminding us that true greatness goes beyond mere victories—it lies in forming lasting bonds between humans and animals amidst thundering hooves and cheering crowds.

Lasting Impact on Horse Racing Community

Charles Kurtsinger made a lasting impact on the horse racing world that still resonates today, showcasing his incredible career. Winning the Kentucky Derby twice in 1925 and 1926 solidified his status as a legend in the sport, proving not only his exceptional talent but also his deep bond with the horses he rode. Fans and fellow jockeys admired Kurtsinger for his strategic skills and natural understanding of horses’ behavior, which allowed him to bring out their best performances.

Off the racetrack, Charles Kurtsinger’s influence can be felt across various facets of modern horse racing. His sportsmanship and dedication to fair play set a high standard that young jockeys strive to follow even now. By embodying values like integrity and respect for both competitors and animals, Kurtsinger created a legacy that goes beyond mere wins or losses. He continues to inspire those who aim for excellence in the sport while honoring its longstanding traditions.

In addition to his accomplishments on track, Charles Kurtsinger’s charitable work highlights his commitment to giving back to the equestrian community. His support for causes aimed at improving racehorses’ conditions shows he was driven by more than personal success – he genuinely cared about these majestic creatures that played such an important role in shaping his remarkable career. Through acts of kindness away from competition, Kurtsinger proved that true greatness isn’t just about winning races but also making meaningful contributions towards enhancing the entire sport overall.


1. What were the years in which Charles Kurtsinger won the Kentucky Derby, and which horses did he ride to victory?

In 1925, Charles Kurtsinger rode Flying Ebony to victory in the Kentucky Derby. Four years later, he claimed another win aboard Clyde Van Dusen in 1929. His exceptional talent and expertise as a jockey were on full display during these historic races.

2. How did Charles Kurtsinger’s riding style set him apart from other jockeys of his time?

Charles Kurtsinger’s exceptional timing and natural talent for connecting with his horse companions enabled him to skillfully maneuver through the fast-paced racetrack environment, distinguishing himself as a highly skilled and graceful jockey during his time.

3. Can you describe some of the key races leading up to Charles Kurtsinger’s Kentucky Derby wins that showcased his exceptional skill?

Before winning the Kentucky Derby, Charles Kurtsinger demonstrated his amazing talent in races like the Santa Anita Handicap and Preakness Stakes. His superb riding skills and smart strategies at these events made him known as a jockey with exceptional abilities.

4. What impact did Charles Kurtsinger have on the world of horse racing beyond his Kentucky Derby triumphs?

Charles Kurtsinger greatly influenced the horse racing world with more than just his two Kentucky Derby wins. His outstanding talent, fair play, and commitment to the sport motivated many jockeys and fans across different generations.

5. How did Charles Kurtsinger’s victories in the Kentucky Derby influence the sport of horse racing during his era and beyond?

Charles Kurtsinger won the Kentucky Derby two years in a row. His wins made him a famous jockey and had a big impact on horse racing. He showed incredible skill and determination, inspiring many riders and fans to follow their dreams in the sport.

6. What qualities or characteristics made Charles Kurtsinger a legendary figure in the history of horse racing, particularly in relation to his Derby successes?

Charles Kurtsinger became a legendary figure in horse racing due to his exceptional riding abilities, strong determination, and close bond with his horses. His masterful performances led to two impressive victories at the Kentucky Derby, securing his place in the sport’s history books.