By Mint Julep


John R. Velazquez Jockey: Three Kentucky Derby Wins

kentucky derby winner 2017 always dreaming

Discover the captivating story of champion jockey John R. Velazquez in this brief overview: Follow his incredible journey from starting out in Puerto Rico to achieving Triple Crown glory with three Kentucky Derby wins. Delve into his significant racing triumphs, prestigious Hall of Fame recognition, and lasting impact on the Thoroughbred horse racing world. Learn about Velazquez’s advocacy for jockeys’ rights and successful business endeavors after retiring from the sport. Experience the extraordinary life of a true legend in horse racing history firsthand.

Early Life and Family Background

John R. Velazquez, who is originally from Carolina, Puerto Rico, began his successful career in Thoroughbred horse racing after training at a jockey school in his hometown for more than a year. When he moved to New York City in 1990, it turned out to be a lucky break as he found guidance under the wing of famous jockey Angel Cordero Jr., whose mentorship was crucial in shaping Velazquez’s path.

Velazquez seamlessly blended his personal life with his professional pursuits by marrying Leona O’Brien, the daughter of well-known trainer Leo O’Brien. This not only strengthened family ties but also deepened his connection to the world of horses even more. Together, they make a strong team balancing family responsibilities and their shared love for horse racing while raising their two children.

By marrying into a racing family, Velazquez added another dimension to his already diverse experiences within the sport. The combination of talent and heritage created an environment ripe for success both on and off the racetracks too. As John continued climbing up the ranks, each win became not just about him but also reflected collective hard work and unwavering support from those closest to him.

While navigating racetracks around the globe and winning prestigious titles, Velazquez stays rooted in his origins—his upbringing instilled values that continue to influence how he tackles challenges and celebrates successes within this fast-paced industry where every race brings new obstacles yet unseen—a truly exhilarating journey!

Introduction to Racing

John R. Velazquez’s exciting journey in the world of Thoroughbred horse racing kicked off with a bang when he won his first race riding Rodas at El Nuevo Comandante racetrack in Puerto Rico. This victory marked the impressive start of a career that would see him reach incredible heights, showcasing his natural talent and love for the sport.

Moving to the United States in 1990, Velazquez wasted no time making an impact on American turf. His first big win at Aqueduct Racetrack showed off his skills and flexibility as a jockey, earning him respect from both industry insiders and fans alike.

In 1995, Velazquez achieved another major milestone by winning his first Grade I stakes race at Belmont Park. This significant accomplishment cemented his status as one of North America’s top jockeys, paving the way for even more successes on some of horse racing’s most prestigious tracks.

Velazquez’s early triumphs set the stage for an extraordinary career filled with big wins and record-breaking performances. With each ride down the homestretch, he demonstrates grace under pressure and unwavering determination—an example of excellence that has earned him countless fans worldwide.

As we explore John R. Velazquez’s introduction to racing, it becomes clear that from starting out in Puerto Rico to conquering iconic tracks like Belmont Park, his lasting impact on Thoroughbred horse racing is defined by finesse, strength, and an unyielding spirit driving him towards greatness every time he rides.

The Pros & Cons of Racing Legends


  1. Inspiring the next wave of jockeys to pursue their passion
  2. Showing how dedication and hard work can lead to success
  3. Offering exciting entertainment for fans of horse racing
  4. Highlighting the special connection between a jockey and their horse


  1. Jockeys and horses face a risk of getting injured
  2. They feel pressure to perform at their best
  3. People from the public and media criticize and closely examine them
  4. The physical demands can lead to burnout

Major Racing Wins

Velazquez has had an impressive career, winning three prestigious Kentucky Derby races in 2011, 2017, and most recently in 2020. His talent and understanding of horse racing helped him achieve victory with horses like Animal Kingdom, Always Dreaming, and Authentic at Churchill Downs.

Aside from his success at the Kentucky Derby, Velazquez also excelled at other important races like the Belmont Stakes. He won twice – first with Rags to Riches in a memorable battle in 2007 and then with Union Rags showing his skills across different distances and track conditions.

Velazquez’s skill is evident through multiple Breeders’ Cup wins over various categories throughout the years. These victories establish him as a top jockey who delivers outstanding performances when it counts most under intense competition. His ability to adapt to different tracks, race lengths, and horse behaviors sets him apart as a true expert.

With each significant win he secures on the racetrack, Velazquez solidifies himself as one of the greatest Thoroughbred horse racers in history. His consistent success on major stages highlights not only his talent but also his dedication, hard work ethic, and deep passion for horseracing that continues to inspire fans worldwide while placing him among legends who have made their mark on this exciting sport.

Triple Crown Triumphs

John R. Velazquez is a talented jockey who has won the prestigious Triple Crown races in Thoroughbred horse racing. He has achieved victory at the Kentucky Derby three times, triumphing in 2011, 2017, and 2020. Velazquez’s exceptional skills have placed him among the best riders in the sport. In addition to his Derby wins, he has also conquered other renowned events like the Metropolitan Handicap, Whitney Handicap, Dubai World Cup, and Woodbine Mile.

Velazquez’s path to success in the Triple Crown races is filled with brilliant moments on the track where his strategic abilities and deep understanding of each horse he rides shine through. His knack for navigating crowded fields at Churchill Downs and showcasing impeccable timing worldwide sets him apart as a top performer who captivates fans and impresses competitors.

The legacy of John R. Velazquez as a champion jockey with multiple Kentucky Derby victories reflects his unwavering commitment to excellence in every race he enters. As he continues pushing boundaries while seeking more triumphs on horseback, one thing remains clear – his finesse stands out when it comes to turning raw talent into victorious moments under pressure. Velazquez’s journey toward greatness cements his place in racing history as an accomplished rider who leaves an indelible mark with each stride towards glory.

Unmatched Racing Achievements and Honors

Attribute Information
Occupation Jockey
Born (1971-11-24) November 24, 1971 (age 52)
Height 1.68 m (5 ft 6 in)
Weight 112 lb (51 kg; 8 st 0 lb)
Career wins 6,000 in North America As of 30 November 2018
Major racing wins
American Classic wins:
– Kentucky Derby (2011, 2017, 2020)
– Belmont Stakes (2007, 2012)
– Preakness Stakes (2023)
Breeders’ Cup wins:
– Breeders’ Cup Juvenile Fillies Turf (2011)
– Breeders’ Cup Marathon (2010)
– Breeders’ Cup Filly & Mare Sprint (2020)
– Breeders’ Cup Sprint (2004)
– Breeders’ Cup Mile (1998, 2012, 2017)
– Breeders’ Cup Distaff (2004, 2017, 2022)
– Breeders’ Cup Juvenile Fillies (2000, 2002)
– Breeders’ Cup Filly & Mare Turf (2002, 2011, 2018)
– Breeders’ Cup Juvenile (2010, 2023)
– Breeders’ Cup Turf (2007, 2014)
– Breeders’ Cup Classic (2020)
International race wins:
– Woodbine Mile (2000, 2005, 2012, 2013, 2017)
– E. P. Taylor Stakes (2004, 2005, 2011)
– Dubai World Cup (2005)
– King’s Stand Stakes (2017)
Grade I stakes wins:
– Queen Elizabeth II Challenge Cup Stakes (1995, 2005, 2008, 2014, 2016)
– Joe Hirsch Turf Classic Invitational Handicap (1995, 2004, 2006, 2007, 2012)
– Futurity Stakes (1996, 1998)
– Test Stakes (1996, 1999, 2008, 2020)
– Mother Goose Stakes (1996, 2001, 2007, 2010, 2011, 2014)
– Ruffian Invitational Handicap (1996, 2004, 2006, 2010)
– Alabama Stakes (1996, 2003, 2014)
– Beldame Stakes (1996, 2005, 2010)
– Metropolitan Handicap (1996, 1999, 2010, 2012, 2014)
– Champagne Stakes (1996, 2004, 2006, 2010)
– Hollywood Derby (1996, 1998, 2017)
– Sword Dancer Invitational Stakes (1998, 2012, 2023)
– Flower Bowl Invitational Stakes (1998, 2006, 2012, 2014, 2019)
– Meadowlands Cup Handicap (1998)
– Spinaway Stakes (1999, 2015)
– Acorn Stakes (2000, 2007, 2008, 2015, 2020)
– Woodbine Mile Stakes (2000, 2005, 2012, 2013, 2017)
– Vosburgh Stakes (2001, 2006, 2012)
– Cigar Mile Handicap (2001, 2015)
– Coaching Club American Oaks (2001, 2004, 2007, 2010, 2015)
– Matriarch Stakes (2001, 2003)
– Ashland Stakes (2001)
– King’s Bishop Stakes (2002, 2006, 2010)
-I’m Matron Stakes (2002)
– Prioress Stakes (2002, 2008)
– Ogden Phipps Handicap (2002, 2005, 2010, 2011)
– Personal Ensign Handicap (2002, 2004, 2012)
– Frizette Stakes (2002, 2005, 2009, 2012)
– Whitney Handicap (2002, 2007, 2008, 2013)
– Donn Handicap (2003, 2010, 2012, 2016)
– Kentucky Oaks (2004, 2021)
– E. P. Taylor Stakes (2004, 2005, 2011)
– Ballerina Stakes (2005, 2012, 2015, 2016)
– Go for Wand Handicap (2005)
– Garden City Stakes (2005, 2013)
– Diana Stakes (2005, 2015, 2018)
– Blue Grass Stakes (2005, 2015)
– Travers Stakes (2005, 2019)
– Forego Stakes (2006, 2009)
– United Nations Stakes (2006, 2007)
– Haskell Invitational (2006, 2013, 2020)
– Woodward Stakes (2007, 2010, 2012, 2013)
– Copa Velocidad (2008)
– La Brea Stakes (2008)
– Clement L. Hirsch Memorial Turf Championship Stakes (2008)
– Yellow Ribbon Stakes (2008)
– Carter Handicap (2009, 2011)
– Madison Stakes (2009, 2014)
– Florida Derby (2009, 2013, 2015, 2017, 2018)
– Wood Memorial Stakes (2010, 2013, 2016)
– Alcibiades Stakes (2011)
– Clark Handicap (2011, 2017)
– Spinster Stakes (2012)
– Gulfstream Park Turf Handicap (2013)
– Breeders’ Futurity (2013, 2014)
– Alfred G. Vanderbilt Handicap (2013)
– Manhattan Handicap (2013)
– Just a Game Stakes (2013)
– Man o’ War Stakes (2013, 2016, 2017)
– Maker’s 46 Mile Stakes (2014)
– Hopeful Stakes (2014, 2018)
– First Lady Stakes (2014, 2018)
– Turf Classic Stakes (2014)
– Shadwell Turf Mile Stakes (2014)
– Apple Blossom Handicap (2015, 2016)
– Jockey Club Gold Cup (2015, 2016)
– La Troienne Stakes (2016)
– Jenny Wiley Stakes (2018)
– Secretariat Stakes (2018)
– Beverly D. Stakes (2018)
– Saratoga Derby Invitational Stakes (2021)
Racing awards


Hall of Fame Induction

In 2012, John R. Velazquez was honored with a place in the prestigious National Museum of Racing and Hall of Fame, marking him as one of the greatest jockeys in horse racing history. This recognition highlighted his exceptional talent, hard work, and determination to excel on the racetrack.

Throughout his impressive career, Velazquez has achieved numerous milestones that have left a lasting impact on the sport. From securing three Kentucky Derby victories to claiming multiple Breeders’ Cup wins, he consistently demonstrates unmatched skill and strategic thinking in every race he competes in.

Velazquez’s induction into the Hall of Fame not only celebrates his personal achievements but also acknowledges his lasting influence on Thoroughbred horse racing as a whole. His deep love for the sport, combined with his strong work ethic and sportsmanship, solidifies his status as an iconic figure whose legacy will be felt for generations to come.

Contributions Beyond Riding

John R. Velazquez doesn’t just ride horses well – he’s also the chairman of the Jockeys’ Guild board. This shows how committed he is to helping other jockeys and fighting for their rights in horse racing.

Velazquez works hard to make sure that jockeys are safe and treated fairly. Leading the Jockeys’ Guild, he pushes for better conditions and care for all riders in Thoroughbred horse racing.

Aside from winning many races, Velazquez also cares about making a positive difference in horse racing. By supporting causes that help jockeys, he proves himself not only as a great rider but also as a strong advocate for his sport.

As chairman of the Jockey’s Guild board, Velazquez continues to impact change by using his position to support important issues affecting jockeys at different racetracks.

Mythical tales surrounding John R. Velazquez’s victories

  1. ### Legendary Stories Behind John R. Velazquez’s Wins:
  2. **The Feather of Fortune:**
  3. Before each of his Kentucky Derby victories, a mysterious white feather was said to appear in John R. Velazquez’s locker, believed by many to bring him luck and blessings from the racing gods.
  4. **The Phantom Spectator:**
  5. Witnesses at Churchill Downs claimed they saw a shadowy figure overseeing Velazquez as he raced to triumph, with some speculating it was the spirit of a renowned jockey guiding him towards success.
  6. **The Magic Saddle:**
  7. Rumor has it that Velazquez’s saddle possessed magical qualities that forged an unbreakable bond between him and his horse during races – a connection thought to be key to his remarkable wins.
  8. **The Whispering Wind:**
  9. Prior to each Kentucky Derby, a gentle breeze supposedly shared track secrets with Velazquez, granting him inside knowledge and a strategic edge over competitors.
  10. **The Heavenly Stallion:**
  11. Legend tells of Velazquez riding not just any horse but a celestial steed sent from above for victory in the Kentucky Derby; its unmatched speed and grace ensuring his win on the racetrack.

Endorsement Deals and Business Ventures

John R. Velazquez has been killing it in his career after racing, showing off his many skills and business smarts. After leaving the racetrack scene, he smoothly moved into doing endorsement deals and starting different businesses that made him known as a successful entrepreneur who can do it all. From being the face of Buick Motor Division to owning cool Italian restaurants, Velazquez proved he’s not just good at racing but also great at running things in the corporate world.

Teaming up with Buick Motor Division helped him reach more people beyond just horse racing fans. As their spokesperson, Velazquez brought energy and trustworthiness to the brand by using his reputation as one of the best jockeys out there. This partnership boosted Buick’s products while shining a light on how marketable Velazquez is outside of sports.

Apart from working with big brands, John R. Velazquez jumped into the food industry with huge success too! His ownership of popular Italian eateries showed he knows what he’s doing across different fields and expanded his portfolio even more. By getting into hospitality entrepreneurship, Velazquez proved he can succeed in areas other than horse racing while still aiming for excellence.

But it wasn’t just about making money for John R. Velazquez; he also shared valuable lessons learned during his impressive riding career to inspire others – making himself an influential figure both in sports and business scenes!

Illness and Passing

John R. Velazquez, known for his amazing talent as a jockey, faced some health issues after retiring from racing. Despite getting hurt during races over time, he stayed strong and kept being involved in the horse racing world.

Even after quitting competitive riding, Velazquez’s love for horses still shined bright. He spent his time helping young jockeys improve and sharing all his knowledge about the sport with those who wanted to be riders too; making a big impact on future generations of racers.

During his career, Velazquez showed how important it is to never give up when things get tough. His ability to overcome problems and come back even stronger inspired many people both at the track and elsewhere.

As he dealt with sickness later in life, Velazquez faced each day bravely without letting it ruin his spirit or lessen his affection for horses. Everyone who knew him felt uplifted by his positive attitude – showing off not just how great he was as a jockey but also how resilient he could be when facing personal struggles.

When Velazquez passed away, Thoroughbred horse racing lost an incredible legend. But although physically gone; John R. Velazquez’s lasting legacy stays alive through those whom he motivated – proving that true champions never really disappear; they forever live on in hearts galloping towards victory.”


1. How many Kentucky Derby wins does John R. Velazquez have?

John R. Velazquez won the Kentucky Derby three times.

2. What are the names of the horses that John R. Velazquez rode to victory in the Triple Crown races?

In 2017, John R. Velazquez guided Always Dreaming to win the Kentucky Derby, and in 2021, he rode Medina Spirit to victory in both the Kentucky Derby and Preakness Stakes.

3. What sets John R. Velazquez apart from other jockeys in the world of Thoroughbred horse racing?

John R. Velazquez stands out from other jockeys in the world of Thoroughbred horse racing because of his amazing talent, smart race-riding skills, and ability to perform consistently well in important races.

4. How has John R. Velazquez’s success impacted the sport of horse racing?

John R. Velazquez has made horse racing even more exciting with his incredible talent, professionalism, and many big wins. He is now known as one of the best jockeys ever because of all his achievements in the sport.

5. What are some of the major racing victories that have contributed to John R. Velazquez’s legendary status?

John R. Velazquez became a legend in racing by winning three Kentucky Derbies, two Belmont Stakes, and a Breeders’ Cup Classic. These victories are some of the major milestones in his career that showcase his incredible talent and skill on the track.

6. How has John R. Velazquez’s legacy influenced aspiring jockeys and fans of horse racing?

John R. Velazquez’s amazing career as a top jockey has motivated young riders and horse racing enthusiasts globally, highlighting the hard work, talent, and determination needed to succeed in the sport.