By Mint Julep


J. K. L. Ross Owner: One Kentucky Derby Winner

1919 kentucky derby winner sir barton

Explore the incredible life of J.K.L. Ross, a Canadian legend celebrated for his wide array of passions including business, philanthropy, and triumphs in thoroughbred racing. Dive into his exceptional sportsmanship, generosity, and lasting impact that extends beyond horse racing to influence diverse areas across Canada and around the world.

Early Life and Family Background

J.K.L. Ross was born in Lindsay, Ontario in 1876 to parents James Leveson Ross and Annie Kerr. He grew up in a family linked to the Canadian Pacific Railway, with his father being instrumental in its construction and known for his impressive art collection. This environment fueled J.K.L.’s entrepreneurial drive from an early age.

Being exposed to both business acumen and cultural interests during his upbringing, J.K.L. developed a strong passion for diverse fields beyond railways such as real estate development and mining operations.

Despite starting from a privileged background, J.K.L.’s success did not come easily; he had to work hard and remain determined throughout his journey from Lindsay to becoming one of Canada’s most respected figures. His story highlights not only his perseverance but also his commitment to making a lasting impact across different areas of influence.

Business Ventures

J.K.L. Ross made a big splash in the business world, teaming up with Sir Herbert Holt in 1911 to create Côte St. Luc Realties. This move set the stage for developing Hampstead, Quebec and marked his entry into real estate—an area where he would make a lasting impact.

Venturing beyond just property development, Ross also took charge of managing his family’s coal and steel businesses after his father passed away. Embracing this responsibility not only showcased his skills but also highlighted his dedication to carrying on the legacy left by previous generations.

While juggling multiple businesses, J.K.L. Ross wasn’t afraid to get hands-on with projects close to home—literally! Building his own house on Peel Street in Montreal was more than just a smart investment; it was a personal touch that added character to the cityscape.

Ross tackled business endeavors with enthusiasm and commitment, showing resilience even during tough times. His ability to navigate financial challenges while keeping various ventures running smoothly demonstrated both sharp entrepreneurial skills and unwavering determination.

From laying the groundwork for new towns to steering family enterprises towards success, J.K.L. Ross displayed versatility that went beyond just making money—a savvy businessman whose impact reached far beyond mere numbers on financial statements.

The Pros & Cons of Equine Legacy and Influence


  1. A long history of being the best in horse racing
  2. Shaping the growth of the Canadian horse racing scene
  3. Setting an example for upcoming generations of riders
  4. Giving back through charity work and philanthropy


  1. Narrowing the attention to a particular area within the horseback riding community
  2. Risk of outshining other significant individuals in the history of horse racing
  3. Debates or objections regarding business strategies or personal affairs
  4. Difficulties in staying current and influential as time goes on

Tuna Fishing

In 1911, J.K.L. Ross’s passion for deep-sea fishing bloomed while he was at St. Anns Bay in Nova Scotia. He made history by catching a massive 680-pound tuna, setting a new world record and showcasing his exceptional skills on the open waters.

But Ross didn’t stop there – driven by his love for angling, he developed innovative techniques that transformed tuna fishing into the sport we know today. His dedication paid off when he surpassed himself by reeling in an even bigger 720-pound behemoth from the ocean depths.

The thrill of battling such powerful creatures like tunas deeply resonated with Ross, inspiring him to push boundaries and explore uncharted territories in deep-sea fishing. Each expedition wasn’t just about breaking records; it was about immersing in nature’s beauty and experiencing firsthand the raw might of these majestic marine giants.

Ross’s remarkable achievements weren’t just personal triumphs; they embodied his unwavering spirit and resilience against challenges both on land and sea alike. His legacy goes beyond numbers or statistics; it reflects a strong bond between humans and nature, showing what can be achieved through dedication to one’s craft.

By capturing breathtaking moments beneath vast skies and seas, J.K.L. Ross left an unforgettable mark on angling – a legacy that continues to inspire fishermen young at heart to appreciate our oceans’ wonders for years ahead.

World War I Contributions

During World War I, J.K.L. Ross demonstrated his strong sense of generosity and patriotism by generously donating three large yachts to the Royal Canadian Navy. This act showcased his unwavering commitment to supporting his country in times of need. Not only did he provide resources, but he also personally led one of the vessels himself, showing his hands-on approach and dedication to the cause. His remarkable actions earned him a prestigious appointment as Commander of the Order of the British Empire for his exceptional service—a well-deserved recognition for someone who gave so much during such challenging times.

Ross’s involvement in naval operations during World War I not only highlighted his philanthropic spirit but also underscored his versatility and adaptability across different fields. Transitioning from successful business ventures to commanding a vessel at sea exemplified Ross’s ability to excel outside conventional realms—a true testament to his courage and leadership qualities under pressure. His willingness to step up when duty called speaks volumes about his character, showcasing an individual whose contributions extended far beyond financial support or professional success into realms where true heroism resides.

Reflecting on J.K.L. Ross’s extraordinary legacy intertwined with World War I history reveals that he was more than just a businessman or sports enthusiast—he was a multifaceted individual whose impact reverberated through various spheres of influence. From navigating high-stakes business deals to steering naval vessels towards victory, Ross embodied resilience, determination, and selflessness throughout challenging times—qualities that continue inspiring admiration today.

His enduring legacy serves as a reminder that one person’s actions can ripple through time leaving behind an indelible mark on history—an inspiring tale woven into Canada’s rich tapestry of heroes past and present.”

J.K.L. Ross: Life in Brief

Category Data
Born John Kenneth Leveson Ross
31 March 1876
Lindsay, Ontario, Canada
Died 25 July 1951 (aged 75)
Montego Bay, Jamaica
Education Bishop’s College School
Alma mater McGill University
Occupation(s) Businessman, philanthropist and racehorse owner/breeder
Spouse(s) – Ethel Matthews (m. 1902; div. 1930)
– Iris de Lisser (m. 1931)
Children – James K. M. Ross
– Hylda A. M. Ross Hodgson
Parent(s) James Ross and Annie Kerr


During World War I, J.K.L. Ross made significant donations that had a lasting impact on educational and healthcare institutions. His generosity towards Bishop’s College School and McGill University in funding new buildings showed his dedication to creating better learning environments for future generations.

Ross gave an impressive $1 million to expand the Royal Victoria Hospital, improving medical care accessibility for many people in need. These large donations not only showcased his financial capability but also revealed his strong belief in giving back to society and supporting essential infrastructure for community well-being.

Amidst the chaos of war, Ross’s commitment to philanthropy highlighted not just his wealth but also his compassion and altruism. His legacy as a benefactor continues to inspire others today by emphasizing the importance of using resources for noble causes that can make a positive impact on society long after one is gone.

Thoroughbred Racing Success

After World War I, J.K.L. Ross made a legendary entrance into the world of Thoroughbred horse racing. His ownership of top racehorses led to his peak moment with Sir Barton, who won the prestigious U.S Triple Crown in 1919 – making him the American Horse of the Year. Ross’s stable wasn’t just successful once; other standout horses like Damrosch and Cudgel also excelled under his guidance.

J.K.L. Ross was all about winning in Thoroughbred racing success. His horses didn’t just participate; they dominated races with an aura of invincibility that left spectators amazed. The legacy he created on racetracks throughout North America went beyond trophies or awards – it focused on pushing limits, breaking records, and showing true sportsmanship at its best.

Ross’s love for horse racing wasn’t just a pastime; it was an art that he mastered with skill and commitment akin to a conductor leading a symphony. Every race became his canvas where he showcased excellence, turning competitions into grand displays worthy of admiration from fans everywhere.

In Thoroughbred racing circles, J.K.L. Ross stood out not only for victories but also for his unwavering dedication to fair play and integrity in an industry often filled with controversies and scandals. He embodied good sportsmanship by ensuring respect for fellow competitors remained crucial even amid fierce competition.

Beyond being recognized as a giant in Thoroughbred racing circles, J.K.L. Ross’s influence extended far beyond the track itself – leaving behind a lasting legacy marked by generosity towards charitable causes and an indomitable spirit that inspired many around him to strive for greater heights both within sporting arenas and outside them too

Legendary lore surrounding Kentucky Derby champion J. K. L. Ross

  1. Legendary stories about J. K. L. Ross, the owner of the 1914 Kentucky Derby champion Old Rosebud:
  2. **Unique Training Techniques**: J.K.L Ross had a reputation for using unconventional training methods with his horses, like having them swim regularly in a custom-made pool at his Maryland estate.
  3. **Record-breaking Win**: When Old Rosebud won the 1914 Kentucky Derby, he not only impressed but also set a new track record for the 1 and 1/4 mile race distance by finishing in just 2 minutes and 3/5 seconds.
  4. **Vibrant Personality**: Known for his vibrant personality in horse racing circles, J.K.L Ross stood out with his extravagant lifestyle, love of fast cars, and distinctive fashion sense – often seen donning brightly colored suits and hats at racetracks.
  5. **Good Luck Charm**: It’s believed that on race days, J.K.L Ross always kept a lucky silver dollar in his pocket which he would rub before big races to bring him good fortune – including during the prestigious Kentucky Derby.
  6. **Philanthropic Spirit**: Apart from excelling in horse racing, J.K.L Ross was recognized for his philanthropy work where he generously supported charitable causes dedicated to animal welfare and education alongside various other organizations.

Reputation for Sportsmanship

Known for his sportsmanship and generosity, despite facing financial ups and downs from splurging on racing operations, parties, yachts, and more. The media dubbed him “the best sportsman Canada has ever seen.” He was famous for giving back winnings when he noticed any irregularities, even though he could have legally kept them.

Struggling financially led to bankruptcy in 1928 after inheriting $16 million earlier but not seeing the expected returns on investments. High expenses from maintaining racing stables forced him to shut down all operations by 1928.

After a divorce from his first wife Ethel Matthews in 1930 following the bankruptcy struggles, Ross remarried Iris de Lisser in Jamaica. He spent his final years fishing until passing away at home in Montego Bay in 1951. His wish to be buried at sea was fulfilled as requested.

J.K.L.Ross was posthumously honored with induction into the Canadian Horse Racing Hall of Fame (1976). His legacy lives on through pioneering contributions to tuna fishing techniques and remarkable philanthropy. Notably known for Sir Barton’s Triple Crown win among other influences beyond horse racing across Canada and beyond that still endure today.


1. How did J.K.L. Ross first become involved in thoroughbred horse racing?

J.K.L. Ross got into thoroughbred horse racing because of his love for sports and ability to spot talent, which led him to create a top-notch racing stable that gained fame in the horse racing world.

2. What were some of the key business ventures that J.K.L. Ross was known for outside of horse racing?

J.K.L. Ross was not just a famous racehorse owner – he also delved into various business ventures like mining, real estate, and aviation.

3. Can you elaborate on J.K.L. Ross’s philanthropic efforts and contributions to society?

J.K.L. Ross made a name for himself not just in the business world and horse racing, but also through his philanthropy. His generous donations helped many different causes and communities, making him a Canadian icon known for giving back.

4. How did J.K.L. Ross’s sportsmanship and generosity shine through during his time as a prominent figure in horse racing?

J.K.L. Ross demonstrated remarkable sportsmanship and generosity by consistently backing the sport of horse racing, assisting fellow competitors, and contributing to various charitable causes. These actions have firmly established him as a beloved Canadian figure whose legacy endures today.

5. What challenges did J.K.L. Ross face during his career, and how did he overcome them?

J.K.L. Ross tackled financial difficulties head-on and conquered them through his strong sportsmanship, various business endeavors, and commitment to giving back. He has left a powerful legacy as a Canadian icon celebrated for excelling in thoroughbred racing and more.

6. In what ways has J.K.L. Ross left a lasting legacy beyond his success in thoroughbred racing?

J.K.L. Ross built a strong legacy that goes beyond just winning in horse racing. He did this by starting different businesses, doing charitable work, and always showing good sportsmanship. This made him a well-known Canadian figure admired for his outstanding achievements in various areas of life.