By Mint Julep

Jerry Bailey Jockey: 2 Kentucky Derby Wins From 8 Mounts

1993 sea hero kentucky derby winner

Key Takeaways

  • Jerry Bailey won 2 Kentucky Derby races out of 8 rides, demonstrating his exceptional talent and commitment in one of horse racing’s most prestigious events.
  • Throughout his impressive career, he achieved over 5,800 wins and earned $296 million. He also triumphed in Triple Crown races and the Breeders’ Cup Classic, cementing his position as one of the greatest jockeys ever.
  • Bailey didn’t just excel on the track; he also advocated for jockeys’ rights and smoothly transitioned to a successful broadcasting career after retiring. His impact on the sport is undeniable.

Early Life and Family Background

Jerry D. Bailey, a native of Dallas, Texas, was born on August 29, 1957. He was first introduced to the exciting world of thoroughbred racing at a young age when his father started working with claiming horses at Sunland Park Racetrack. In 1974, Jerry had his very first ride at Sunland which kickstarted an amazing career as a jockey. Growing up around horse racing allowed Jerry Bailey to develop his skills and passion for the sport from early on.

As years passed after that initial ride in 1974 at Sunland Park Racetrack, Jerry Bailey worked hard to become one of the most celebrated jockeys in history. His dedication and focus were evident in every race he participated in, leading him to incredible victories that amazed spectators with his talent and expertise while riding.

What set Jerry Bailey apart from other riders in the competitive world of horse racing was not only his exceptional abilities but also his determination to succeed against all odds. Going from watching races with his dad as a kid to winning the Kentucky Derby twice showcased how persistence combined with natural talent can guide someone towards extraordinary achievements no matter their background – serving as an inspiration for aspiring riders worldwide.

Career Accomplishments

Jerry Bailey, a legendary figure in horse racing with an impressive record of 5,893 career wins and earnings totaling $296 million over his remarkable 31-year career, has firmly established himself as one of the all-time greats. His impact goes beyond just winning races; he has made a lasting mark on the sport through his exceptional talent and unwavering dedication. Bailey’s unmatched ability to handle different tracks and horses sets him apart as a formidable competitor every time he mounts up.

His double victories in each Triple Crown race showcase Jerry Bailey’s extraordinary skill and adaptability as a jockey. These prestigious wins are not mere luck but rather reflections of his strategic approach, precise timing, and deep understanding of horse behavior. The Breeders’ Cup Classic is highly esteemed within the racing community, where Bailey shines brightly with five triumphs under his belt. His consistent success at such high-stakes events speaks volumes about his unparalleled talent on the racetrack.

In an industry as competitive and demanding as horse racing, Jerry Bailey’s accomplishments stand out like guiding lights amid turbulent waters. His legacy surpasses mere statistics; it embodies resilience, passion for excellence, and an unyielding commitment to mastering this intricate dance between man and beast known as horse racing. Fans reflecting on Bailey’s illustrious career filled with unforgettable moments etched into history books know they witnessed greatness personified whenever he adorned those silks and stepped onto that hallowed turf or dirt track alike.

The Pros & Cons of Racing Legends


  1. Jerry Bailey is known for his exceptional skills and expertise in horse racing.
  2. He won two Kentucky Derby victories in just 8 mounts, showcasing his impressive record.
  3. Bailey has a talent for forming strong partnerships with horses, leading to successful races.
  4. His dedication and commitment to the sport of horse racing are unwavering.
  5. Aspiring jockeys look up to Bailey due to his influence and significant contribution to the racing community.
  6. His remarkable achievements serve as inspiration for many.


  1. Being a jockey involves intense physical demands and risks.
  2. Injuries can happen during races, affecting both the jockey and the horse.
  3. Horse racing is highly competitive, creating pressure for jockeys like Bailey.
  4. Jockeys face challenges in staying at their best throughout their careers.
  5. Pursuing a career in horse racing requires sacrifices in personal life and time with family.
  6. Top jockeys like Jerry Bailey may deal with scrutiny and criticism from the public.

Hall of Fame Induction

In 1995, Jerry Bailey proved himself as one of the greatest jockeys in horse racing history by winning two Kentucky Derbies out of eight mounts. His exceptional talent and dedication to the sport were on full display every time he hit the track. Bailey skillfully maneuvered through tough competition in prestigious races with a mix of finesse and expertise.

Beyond his Derby wins, Bailey’s success extended far and wide; he clinched the Eclipse Award for Outstanding Jockey an impressive seven times. This recognition highlighted his unmatched skills and consistent top-notch performances. What set Bailey apart from others was his ability to build strong partnerships with both horses and trainers.

The Kentucky Derby is famously known as “The Most Exciting Two Minutes In Sports,” making a single win a remarkable feat on its own. To triumph in this race twice showcased Jerry Bailey’s mastery on horseback like no other achievement could have done. His victories represented not just crossing that finish line first but also years of hard work, determination, and unwavering passion for excellence within horse racing.

Bailey’s induction into the United States Racing Hall of Fame wasn’t just a formality—it stood as proof of his significant impact on the sport. His legacy continues to inspire young jockeys worldwide who aspire to greatness both on and off the racetrack. By joining other legends in horse racing history, Jerry Bailey cemented himself as an icon whose influence will resonate for generations ahead.

Reflecting back on Jerry Bailey’s incredible journey—from humble beginnings to becoming a household name in horse racing—inspires admiration among fans across the globe today at age 40! His relentless pursuit of excellence serves as motivation for all those dreaming big within such a competitive industry where victory or defeat hinges precariously – much akin to navigating tight turns during high-stakes races!

Major Racing Wins

Jerry Bailey achieved an impressive feat by winning the Kentucky Derby twice out of 8 attempts during his illustrious career as a top jockey in horse racing history. His exceptional skills, dedication, and precision on the track have cemented his legacy as one of the greatest in the sport. He didn’t just excel in one race but showcased his talent across various prestigious events like the Preakness Stakes and Belmont Stakes.

The Kentucky Derby is known worldwide for its rich heritage and fierce competition, making victory there a significant accomplishment. Winning this iconic race not once but twice required immense skill, strategic thinking, and nerves of steel. Jerry Bailey’s ability to navigate through a crowded field with perfect timing demonstrates his expertise as a skilled jockey.

In horse racing, where every second counts, succeeding at high-stakes events like the Derby demands more than luck – it requires unwavering commitment to excellence honed over years on tracks around the globe. Bailey’s triumphs against tough competitors reflect not only his exceptional talent but also his relentless pursuit of perfection with each ride.

Another highlight in Jerry Bailey’s list of major wins is conquering first place at the Dubai World Cup two years consecutively (1996-1997), showcasing both consistency and adaptability on an international stage known for fierce competition. His versatility shines through as he excels under different conditions without missing a beat.

Looking back at Jerry Bailey’s unforgettable moments riding champion horses to victory at legendary races such as The Kentucky Derby or Dubai World Cup serves as inspiration for young riders everywhere – proof that determination and perseverance can overcome any obstacle one race at a time.

Legendary Jockey: Jerry Bailey’s Racing Achievements

Jerry Bailey Occupation Broadcaster, former jockey
Born August 29, 1957 Dallas, Texas, United States
Career wins 5,893
Major racing wins
New York Handicap Triple (1984)
Jaipur Stakes (1984, 1991, 1993, 1998, 2001, 2002)
Bonnie Miss Stakes (1993, 1996, 2000, 2001, 2005)
Dubai World Cup (1996, 1997, 2001, 2002)
Prince of Wales’s Stakes (2000)
Hollywood Gold Cup (1992, 1995, 1998, 1999, 2003)
Pacific Classic Stakes (2004)
Del Mar Futurity (2000)
Palomar Breeders’ Cup Handicap (2005)
Madison Stakes (2005)
Arkansas Derby (1988)
Pimlico Special (1995, 1997, 2001)
Jockey Club Gold Cup (1995, 1997, 2001)
Arlington Million (2000, 2002)
Kentucky Oaks (1993, 2001, 2005)
American Classics wins:
Kentucky Derby 1996 and 1993
Preakness Stakes (1991, 2000)
Belmont Stakes (1991, 2003)
Breeders’ Cup wins:
Breeders’ Cup Juvenile Fillies (1995, 1999)
Breeders’ Cup Juvenile (1996, 1998, 2000)
Breeders’ Cup Filly & Mare Turf (1999, 2000)
Breeders’ Cup Sprint (2001, 2002)
Breeders’ Cup Mile (2003)
Breeders’ Cup Classic (1991, 1993, 1994, 1995, 2005)
Racing awards
George Woolf Memorial Jockey Award (1992)
Mike Venezia Memorial Award (1993)
United States Champion Jockey by earnings (1995, 1996, 1997, 2001, 2002, 2003)
Big Sport of Turfdom Award (1996)
Eclipse Award for Outstanding Jockey (1995, 1996, 1997, 2000, 2001, 2002, 2003)
Honours United States Racing Hall of Fame (1995)
Significant horses Black Tie Affair, Sea Hero, Fit to Fight
Cigar, Arcangues, My Flag, Skip Away
Royal Anthem, Hansel, Real Quiet
Six Perfections, Dubai Millennium, Grindstone, Concern
Congaree, Victory Gallop, Medaglia d’Oro
Candy Eclair, Empire Maker, Saint Liam
Jockeys’ Guild President Bill Shoemaker (Preceded by), 1989–1996, Gary Stevens (Succeeded by)

Saratoga Success

Jerry Bailey had a remarkable run at Saratoga Race Course. He totally dominated the competition by winning seven riding championships between 1994 and 2001, showing off his skills and talent on one of America’s top race tracks. With a grand total of 693 wins at Saratoga, Bailey set a record that held strong for over ten years until it was finally beaten in 2013.

Bailey’s legacy at Saratoga Race Course truly shows how exceptional he was as a jockey. His consistent performance and smart tactics allowed him to outperform his rivals time after time during those exciting racing seasons. The sheer number of victories he achieved at such an esteemed venue really speaks volumes about his dedication to the sport and incredible skill in the saddle.

In history, very few jockeys have been able to leave such an unforgettable mark on a racetrack like Jerry Bailey did at Saratoga. His record-breaking success not only proved that he belonged among the best but also inspired others who dreamt of making their own impact in horse racing. Bailey’s achievements stand as proof of hard work, perseverance, and unwavering love for the sport—a true example of excellence in the world of horse racing.

Contributions Beyond Riding

Jerry Bailey didn’t just excel on the racetrack – he also championed for the rights of jockeys during his time as President of the Jockeys’ Guild from 1989 to 1996. Even after retiring, his involvement in horse racing continued through his role as a television commentator. Bailey’s impact went beyond riding; he possessed leadership and communication skills that not only helped fellow riders but also educated viewers about the sport.

As President of the Jockeys’ Guild, Bailey tirelessly worked to enhance safety standards, insurance coverage, and overall working conditions for jockeys across the industry. His efforts led to significant improvements that are still benefiting riders today, proving his influence extends far beyond the racetrack.

After hanging up his saddle in 2005, Jerry Bailey transitioned into a television commentator where he provided valuable insights and analysis during major horse races broadcasts. He had a unique ability to explain complex race tactics in an understandable way that resonated with audiences worldwide, solidifying his reputation not just as an outstanding rider but also an exceptional communicator within the sport.

Jerry Bailey’s roles both as a top jockey and influential advocate highlighted his diverse talents in horse racing. Whether guiding horses towards victory or sharing wisdom from behind the microphone, he consistently showcased grace under pressure coupled with profound knowledge – leaving behind a lasting legacy that shaped competitive dynamics on race days while influencing public perceptions of this beloved sport.

By recognizing Jerry Bailey’s contributions off-track – advocating for better conditions for jockeys alongside providing insightful commentary – we can see how much more impactful he was than simply winning prestigious races like Kentucky Derby victories. Through unwavering dedication shown through actions and words across various aspects of horse racing culture, he has left behind an enduring mark impacting generations past and present significantly shaping those yet-to-be-written chapters awaiting future enthusiasts eager to absorb their wisdom around tracks globally.”

Legendary Jockey: Derby Triumphs and Racing Myths

  1. Title: The Exciting Journey of a Winning Jockey
  2. Jerry Bailey, an accomplished jockey, clinched victory at the Kentucky Derby twice in his esteemed career. His first triumph was in 1993 aboard Sea Hero, followed by another win on Grindstone in
  3. Although Jerry Bailey only secured two wins at the Kentucky Derby, he boasted an impressive track record with numerous victories in prestigious races like the Breeders’ Cup Classic and the Belmont Stakes.
  4. A fascinating legend about Jerry Bailey suggests that he possessed a unique talent for understanding horses’ personalities and preferences to lead them to success – as if he could “talk” to them. While this claim may be exaggerated, it is true that Bailey had exceptional communication skills and built strong connections with the horses he rode.
  5. Known for his strategic race-riding approach, Jerry Bailey earned the nickname “The Ice Man” because of his calm composure under pressure. He was admired for making quick decisions during races that often resulted in triumphs.
  6. Even after retiring from professional racing, Jerry Bailey remains active in the horse racing industry as a television analyst and commentator. Through sharing his insights and expertise with audiences worldwide, he continues to stay connected to his passion for horse racing.

Controversies and Challenges

Throughout Bailey’s career, he faced his fair share of controversies. One notable incident occurred during the 2004 Belmont Stakes when accusations swirled around him over his ride on Eddington, impacting Smarty Jones’ chance at a Triple Crown victory. The aftermath of that race brought intense scrutiny upon Bailey and somewhat tarnished his otherwise excellent reputation in the racing community.

In addition to this, legal battles arose concerning advertising patches on jockey pants, further complicating Bailey’s already demanding career as one of horse racing’s top figures. Despite these challenges, Bailey remained focused and committed to his craft, navigating through tough times with resilience and determination.

The controversies and obstacles that Jerry Bailey encountered were true tests of his character throughout his illustrious career. While criticism and legal disputes might have discouraged others, Bailey continued to handle pressure gracefully which is why he is considered one of the greatest jockeys in history. His ability to overcome adversities both on and off the track only added more layers to his remarkable legacy in horse racing world.

Retirement and Transition to Broadcasting

On January 19, 2006, Jerry Bailey announced that he was retiring from professional horse riding after a successful career filled with awards and achievements. After retiring, he started working as a racing analyst for ESPN and later moved to NBC when ESPN stopped covering horse racing.

Jerry Bailey quickly became a favorite among fans in his new role as an analyst due to his insightful commentary and deep knowledge of the sport. He was able to analyze races with great accuracy and provide unique perspectives that were well-received by both viewers and industry experts.

During his riding career, Jerry Bailey won the Kentucky Derby twice out of eight attempts. His expertise from being in high-stakes races like the Derby added valuable insights to his broadcasts. Drawing on his own experiences, he brought a level of understanding that fascinated audiences and helped them better appreciate the complexities of horse racing.

In addition to sharing information, Jerry Bailey’s love for horse racing shone through in every broadcast. His enthusiasm and genuine passion not only educated viewers but also created a stronger bond between fans and the exciting world of equine competition.

Lasting Legacy

Considered one of the greatest jockeys in history, Jerry Bailey’s amazing track record speaks volumes. Despite riding in just 8 races at the prestigious Kentucky Derby, he managed to win twice – a remarkable achievement that highlights his exceptional talent and ability to handle pressure on horse racing’s biggest stage.

Bailey’s triumphs at the Kentucky Derby not only cemented his status as a legend but also showcased his unwavering commitment to mastering the art of riding. His careful preparation and strategic approach set him apart, enabling him to tackle the challenges of high-stakes races with finesse and accuracy.

In addition to his wins at Churchill Downs, Bailey boasts an impressive career filled with numerous accolades and victories across various events. From conquering Breeders’ Cup races to earning multiple Eclipse Awards for Outstanding Jockey, he consistently raised the bar for excellence in horse racing during his time.

As fans look back on Jerry Bailey’s lasting impact, they are reminded not only of his two unforgettable Kentucky Derby wins but also of a broader story marked by passion, persistence, and an unyielding pursuit of greatness both on and off the racetrack. His influence goes beyond mere numbers; it stands as proof of what can be accomplished through skill honed by hard work and an enduring love for the sport.


1. How many Kentucky Derby wins did Jerry Bailey achieve in his career?

Jerry Bailey won the Kentucky Derby two times during his amazing career as one of the best jockeys in horse racing history.

2. What was Jerry Bailey’s win percentage in the Kentucky Derby?

Jerry Bailey had a strong record in the Kentucky Derby, winning 2 out of 8 races for an impressive win rate of 25%.

3. How does Jerry Bailey’s record of 2 wins in 8 mounts compare to other jockeys?

Jerry Bailey won 2 out of 8 races in the Kentucky Derby, showcasing his incredible talent and success. This solidified his position as one of the best jockeys in horse racing history.

4. What are some key factors that contributed to Jerry Bailey’s success in the Kentucky Derby?

Jerry Bailey has been incredibly successful in the Kentucky Derby because of his amazing talent, strong knowledge of race strategies, skill in forming great partnerships with trainers and horses, and his unwavering commitment to the sport.

5. Can you provide insights into Jerry Bailey’s approach and strategy when riding in the Kentucky Derby?

Jerry Bailey excelled in the Kentucky Derby by using precise tactics, deeply understanding his horses, and adjusting to the race’s challenges. He demonstrated great skill and experience as a jockey through his strategic approach.

6. How did Jerry Bailey’s victories in the Kentucky Derby impact his overall legacy as a jockey?

Jerry Bailey’s wins in the Kentucky Derby proved he was one of the top jockeys in horse racing history, displaying his amazing talent and skill on the biggest stage in American horse racing.