The Kentucky Derby – Fame, Fashion and Family Business

by Allen Esrock | Apr 8, 2024 | Celebrating Family Business

The 150th Kentucky Derby, “The Most Exciting Two Minutes in Sports”, is set for May 4th in Louisville, Kentucky. Held on the first Saturday in May at Churchill Downs, the race is the first leg of the American Triple Crown. The Derby is more than a horse race, it is deeply rooted in the American experience.

G4 Hancock Walker, the President of Claiborne Farm which was established in 1910, discusses the importance of the race, “The Kentucky Derby is the pinnacle of horse racing.  Each spring as the new foals are born, the air is filled with hopes and dreams of one day winning the Derby.  We were fortunate enough to win the race in 1984 with a colt named Swale and we’ve been chasing another victory ever since.  The first Saturday in May is what brings national attention to our industry and it’s always fun and exciting each year to watch the best two minutes in sports.  The Kentucky Derby is the main reason most of our clients are involved, trying to one day win a Derby winner of their own.”

Kentucky Derby Facts

  • The Kentucky Derby has never been canceled and is the oldest continuously held sporting event in the United States. The first postponement was in 1945 due to WWII. In 2020, the race was moved to September 5 due to COVID.
  • Mint Julep is the official drink of the race. Attendees drink more than 120,000 of these things during their visit to the track.
  • The 2023 Kentucky Derby attendance topped 150,000. The 2015 Derby drew the largest crowd in the event’s history with 170,500 spectators in attendance.
  • In 1973, Secretariat, the only non-human is be listed as one of the top American athletes of the 20th Century, set the track record that stands to this day, running the race in 1:59.40.
  • The Kentucky Derby trophy is the only solid gold trophy that is annually awarded to the winner of a major American sporting event.
  • Queen Elizabeth II attended the Kentucky Derby five times between 1984 and 2007.

Shutterstock Diane Bondareff

What about those hats?

The tradition of wearing hats to the Kentucky Derby dates back to the early days of the event, where women would don their finest hats as a sign of sophistication and status. Over the years, this tradition has evolved into a vibrant display of creativity and individuality, with attendees looking to stand out from the crowd with their choice of headwear. The Kentucky Derby offers its own 2024 What To Wear style guide so fashionable attendees will find “inspirational looks, accessories and of course, headpieces!”

For true fashionistas, the Longines Kentucky Oaks is a most anticipated part of the Debry experience.  It is America’s premier and most lucrative race for 3-year-old fillies – female horses – held each year on the day before the Kentucky Derby. This feature race is a $1.5 Million Grade 1 stakes race and awards the winning filly a garland of lilies, appropriately named “lilies for the fillies.”

One of the highlights of the day is the Longines Fashion Contest invites spectators to “don your finest, frilliest ensembles, because on Oaks Day, sophistication knows no bounds.”  Despite the frivolity, the Longines Kentucky Oaks is an enormous supporter of women’s health.  The day also includes The Survivors Parade a moving tradition that celebrates breast and ovarian cancer survivors and encourages those still fighting their cancer battle as they march on Churchill Downs’ historic racetrack before the running of the Longines Kentucky Oaks.

Horse racing is the most family business of them all!!!

There are 1000s of industries in which family businesses dominate the market including manufacturing, HVAC, real estate, restaurants, death, fabricated metals, automotive dealerships, automobile manufacturing, trucking & warehousing, and printing & publishing.  What makes horse racing so unique is that almost everybody from across the spectrum of the industry has a connection to a family business.


Due to the tremendous costs of horse racing, there are not as many family business owners in horse racing as in the past.  Some of most successful family business owner/breeders include:

Winchell Thoroughbreds – Joan Winchell and her son, Ron, are partners in continuing the family’s prominent racing and breeding operation started by the late Verne Winchell, Joan’s husband and Ron’s father. Verne Winchell, who died in 2002 at the age of 87, founded the doughnut company Winchell’s and later was the CEO and chairman of the Denny’s restaurant chain.

Three Diamonds Farm – Diamonds Farm was established by Kirk Wycoff and his wife, Debra, in 2008. The name is a salute to their three children. Kirk serves as managing partner of the Philadelphia-based private equity firm Patriot Financial Partners. Jordan Wycoff manages the racing operation.

Gary and May West – The husband and wife have been involved in the Thoroughbred industry for more than 30 years and currently have dozens of horses in training in addition to several broodmares at Dell Ridge Farm in Lexington, Ky.  Their horse, Maximum Security was disqualified from winning the 2019 Kentucky Derby.

Claiborne Farm – For over a century, Clairborne Farm has embodied the history of American horse racing.  While Clairborne has one Kentucky Derby win, Swale in 1984, Claiborne stallions sired six of the thirteen Triple Crown winners the farm is famous for its breeding program which produced six Triple Crown Winners including Gallant Fox, Omaha, Whirlaway, Count Fleet, Seattle Slew and, most famously, Secretariat.

G4 Hanock Walker shares his story about growing up at Claiborne Farm, “Walker discusses life growing up in the family business, “I was lucky to grow up on Claiborne.  As a kid, I played in the creeks, streams and barns, not really understanding what all was around me.  I started working with horses at the age of eight and progressed through all positions on the farm, which helped me learn and gave me a better appreciation of all aspects of each job.  As I grew older, I realized what an honor it is to carry on the legacy that my great grandfather started.  Sometimes I am numb to my surroundings, but I try not to take my position for granted as I understand how blessed I am to be a part of this heritage.  I am doing my best to build upon our past for a successful future.”


The top five winning jockeys in 2023 all grew up in horse racing families:

Irad Ortiz, Jr. – Irad’s grandfather, also named Irad Ortiz, was a jockey, and so are his uncle, Ivan Ortiz, and brother, Jose Ortiz.  He was honored as 2023’s outstanding jockey by Eclipse Award voters for the fifth time in six years after besting his 2022 earnings mark with $39,192,585.

Tyler Gaffalione – Tyler has followed his father, Steve Gaffalione, and grandfather Bobby Gaffalione as jockeys. His grandfather competed in the 1984 Kentucky Derby aboard Rexson’s Hope, and 33 years later Tyler rode Patch in the race.

Flavien Prat – Prat never considered any career other than that of jockey. He grew up around horses with his father, Frederic Prat, who trained harness horses.

Luis Saez – Luis was the fourth-highest earning jockey in 2023 with $23,191,560.  He is also the brother of fellow American Thoroughbred jockey Gabriel Saez.  Their younger brother, Juan Saez, died of an horse racing injury when he was 17 years old.

Jose Ortiz – Jose is the younger brother of Irad Ortiz, Jr.  The pair made headlines on January 20, 2013, when they won the first seven races on Aqueduct’s card with Jose earning three of the wins.


Family business trainers don’t dominate the occupation in the same manner as jockeys.  Still, most of the trainers have family business roots.

Steve Asmussens – Steve started as a jockey and became the all-time leading trainer in North America.  His father, Keith, is a retired jockey and his mother Marilyn is a trainer who became the first woman to win a major quarter horse race.  His brother Cash Asmussens, was also a leading jockey turned trainer, and his sons, Erik and Keith, are jockeys.

Todd Pletcher – Todd was the third winningest trainer in 2023.  He’s the son of trainer Todd Pletcher.

William I. Mott – Bill was the fifth winningest trainer in 2023.  His son, Riley, worked with him for ten years before going out on his own.


What separates horse racing from every other industry is that the main product of the business is a family business.  While a horse’s lineage will play a role in its success on the racetrack, it is the only consideration when it comes to breeding horses.

Galileo (Ireland), the offspring of Sadler’s Wells and Urban Seat, is one of the most successful stallions in horse racing history. Galileo had a very successful racing career earning over $2,000,000.  However, Galileo was one of the greatest sires having sired 338 stakes winners for earnings of over $285-million.  When Galileo died when he was 21, it was reported that he had generated €40m a year in stud fees.

The Kentucky Derby is truly an important part of Americana.  As you settle in with your fancy hats and mint julips to watch “The Most Exciting Two Minutes in Sports”, remember that it’s all about the family business.


CLICK HERE to join us for our APRIL 15 WEBINAR: Family Business and the Kentucky Derby featuring Hall of Fame Jockey – Chris McCarron
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Allen Esrock is the Founder of NxtGen Nexus, a platform for the next generation of family business owners which is based on his experience of growing up in a family business. Prior to that he started Jitter Fingers, the first safe, social networking website for tween girls and their bffs with Jitter Finger clubs in 12+ countries and 250+ cities in the US.

About the Author

Allen Esrock is the Founder of NxtGen Nexus, a platform for the next generation of family business owners which is based on his experience of growing up in a family business. Prior to that he started Jitter Fingers, the first safe, social networking website for tween girls and their bffs with Jitter Finger clubs in 12+ countries and 250+ cities in the US.