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The Beginning: Skeets Holland’s Rise
In a time when Black jockeys were being pushed out of the sport due to the discriminatory policies of the Jim Crow era, Skeets Holland made his mark. While many of the earlier Black jockeys rode when the majority of the field was Black, Skeets’ success came during an era when Black riders were nearly erased from the sport. He wasn’t just a good jockey for his time—he was great in a time when people like him weren’t supposed to win.
Skeets’ tenacity and undeniable talent earned him a place among Maryland’s most celebrated jockeys, despite the doors that were closed to him. His crowning achievement was receiving the prestigious Frederico Tesio Award, presented by Governor William Donald Schaefer, which solidified his status as a Maryland racing legend. The state even honored him with the Skeets Holland Day at Pimlico and named a race in his honor.
A Legacy Built on Grit and Excellence
The story of Holland Stable is not just one of family tradition—it’s a testament to perseverance, skill, and a passion for Thoroughbred racing. What began with Skeets Holland, the first Black jockey to break barriers after Jim Crow, has evolved into a powerhouse operation led by his grandson, Troy Holland, whose vision and dedication have elevated the stable to first-class status.
Growing up just two blocks from Pimlico, Troy’s passion for racing was forged in the shadow of one of the most iconic tracks in Maryland. From a young age, he could hear the roar of the races from his backyard, already part of the winner’s circle with his grandfather and other family members. His uncle, James “Little Skeets” Holland, though too big to become a jockey like his father, was a legend in his own right as one of the best exercise riders and a fearless breaker of young horses.
But Troy’s journey didn’t stop with family connections. He worked his way up from the ground, starting as a groom for Tony Dutrow, Maryland’s leading trainer at the time. Tony recognized Troy’s potential, offering him hands-on mentorship that would later form the backbone of his expertise in preparing horses. Later, Troy was mentored by Dr. Tom Bowman at Northview Stallion Station, the premier stallion operation in Maryland. Despite family obligations that prevented him from taking a full-time role, Troy volunteered at Northview, gaining first-class knowledge from one of the most respected breeding experts in the world.
Troy’s journey wasn’t just about learning the ropes—it was about becoming a force in the Thoroughbred world. From insights shared by his cousin, the leading black trainer in the nation Michael Jones under the guidance of his grandmother and Troy’s trailblazing aunt, Sylvia Rideoutt Bishop, the first licensed Black female trainer in the U.S., to his work with top names in the industry, Troy’s career has been about shattering expectations. Sylvia herself has been immortalized in the Guinness Book of Records and honored with monuments and stakes races in her name. Troy’s experiences make him the perfect leader to carry Holland Stable forward with vision and innovation.
Holland Stable today is more than just a family operation—it’s a first-class establishment with the expertise, knowledge, and pedigree to compete at the highest levels. Troy’s hands-on experience working for Maryland’s top names, coupled with the family’s deep connection to the sport, ensures that the Holland Stable legacy will endure for generations to come.
This isn’t just about horse racing—it’s about breaking barriers and redefining what Black-owned stables can achieve in an industry that hasn’t always been welcoming. While many may operate below first-class standards, Holland Stable stands apart, built on a foundation of excellence, perseverance, and a commitment to winning at the highest levels.
Our goal isn’t just to compete—it’s to win. And as the future unfolds, we’re here to remind the world of the greatness that started with Skeets, lived through Jimmy, and now continues with Troy at the helm.
Honoring the Past, Racing Toward the Future
At Holland Stable, we remember where we came from, but we’re always looking ahead. From claiming our rightful place in the winner’s circle to training the next generation of champion horses, we are dedicated to writing the next chapter in our family’s racing history. And through our partnership opportunities, we invite you to be part of this journey, sharing in the victories and the heritage of a truly legendary stable.