From Churchill Downs to Serenity Ranch

For more than 150 years, the Kentucky Derby has stood as one of the most iconic and prestigious traditions in American history.

Established in 1875 at Churchill Downs in Louisville, Kentucky, the Derby quickly became known as ‘The Most Exciting Two Minutes in Sports’.

Yet, its significance reaches far beyond the race itself. It represents discipline, legacy, culture, and the pursuit of excellence at the highest level.

Unknown to many, however, is that black excellence lies at the very foundation of the Kentucky Derby’s early success. Enslaved African-Americans were the original trainers, caretakers, and jockeys who built the sport into a national institution.

Black jockeys dominated the early years of the Derby, winning 15 of the first 28 races. Their expertise, courage, and mastery helped define thoroughbred racing in America. Despite systemic barriers that later excluded many of these pioneers, their contributions remain permanently etched into the sport’s legacy.

Today, that legacy is not only being honoured; it is being elevated and reclaimed.

Jamaica-born entrepreneur Dr Trisha Bailey has created the Orlando Derby Soirée, an extraordinary cultural and equestrian experience designed to celebrate legacy, inclusion, and excellence with the ultimate level of class and sophistication.

On May 2, the second Orlando Derby Soiree will be held at the Serenity Ranch in Orlando, Florida, bringing together not just lovers of horses, but the fine art of the equestrian experience.

The cultural aspect of the Orlando Derby Soiree will be headlined by R&B artiste KEM, bringing his timeless voice and soulful presence to an evening already defined by elegance and purpose. His performance will serve as a celebration of culture, resilience, and excellence, values that define both the history being honoured and the future being built.

Hosted at the magnificent Serenity Ranch, the Soirée represents what a Derby should be: elegant, inclusive, empowering, and deeply rooted in cultural truth. It brings together distinguished guests, cultural leaders, entrepreneurs, philanthropists, and visionaries in an environment that reflects refinement, unity, and pride.

Bailey said the connection between the historic Kentucky Derby and the Orlando Derby Soirée is both symbolic and powerful.

“The Kentucky Derby represents the foundation, the tradition, the endurance, and the brilliance of those who built the sport. The Orlando Derby Soirée represents the evolution, the ownership, the inclusion, and the rightful elevation of that legacy into the future,” she said.

One of the oldest horse farms in the state of Florida, Serenity Ranch is more than a place of beauty and elite equestrian excellence. It is a symbol of ownership, empowerment, inclusion, and the continuation of a legacy long deserving of recognition.

Beacon of progress

Serenity Ranch itself stands as a beacon of progress.

Under Bailey’s stewardship, she says it has become a place where tradition meets transformation and where excellence is not only celebrated, but owned. It is a space where young men and women of colour can see themselves reflected in leadership, in ownership, and in possibility. It affirms that striving for greatness is not limited by circumstance, but enabled by vision and executed with excellence.

Bailey, a renowned philanthropist and visionary, has emerged as a transformative leader in the equestrian world through her ownership of Serenity Ranch, widely recognised as one of the most prestigious equestrian estates in Orlando, Florida.

Bailey’s leadership represents a profound shift in the narrative of equestrian sport. Her presence affirms that black excellence is not new to this world; it has always existed. What is new is ownership, representation, and the ability to curate spaces where excellence is elevated with intention and dignity.

In honouring this powerful history and ensuring its validation for future generations, the Orlando Derby Soirée is more than an event. It is being hailed as a living tribute, a declaration that greatness is not accidental; it is systematically curated, cultivated, and realised through vision, courage, and purpose.

Through Serenity Ranch and the creation of the Orlando Derby Soirée, Bailey has illuminated the true depth of inclusion. She has created not just an event, but a movement, one that aimes to validate history, celebrate excellence, and ensure that future generations understand that they belong in spaces of prestige, leadership, and influence.

She describes the soiree as her “fun project”.

Bailey said that the Orlando Derby Soiree is giving back to the people of the community.

“It is a way to experience the life you may dream about. It is for a community of people, both Caribbean and others, to experience the highest level of excellence,” she said.

Bailey noted that part proceeds from the Soiree will go towards her Foundation to support single mothers, students’ education and well as to support other charities that support similar causes.

She said ticket sales for this year’s event are ahead of where they were last year.

editorial@gleanerjm.com