At 72 years old, Puerto Rican jockey Jessu Guadalupe defied expectations by winning three races in 2023 at the Camarello racetrack, potentially making him the oldest jockey to win a race in North America—a title once believed held by 71-year-old Perry Uztz in Ohio. Guadalupe’s victories came aboard a horse named Digirade, owned by his son, Jesus Guadalupe’s Destiny Racing PR, marking a remarkable family achievement.
Born on November 6, 1950, Guadalupe remains active in racing, galloping 8-10 horses each morning for trainer Ramon Morales and occasionally competing at Canovanas tracks, with his most recent ride on January 24, 2025. His philosophy is simple: age should never be a barrier if you love what you do and continue to perform well.
Guadalupe’s journey into racing began near a now-closed track where he dreamed of becoming a jockey as a child. At 16, he pursued that dream by working in a stable and racing as an apprentice. Though initially promising, his career faced serious setbacks, including a criminal conviction in New Jersey during the 1970s, which led to 18 months in a youth correctional facility. Afterward, he trained as a barber to support himself before successfully applying to resume his jockey career in Puerto Rico.
Despite challenges in regaining his license in New Jersey and comparisons to figures like Pete Rose who struggled to reclaim their reputations, Guadalupe focused on his career in Puerto Rico. There, he achieved notable success, including guiding Prince Crystal to a St. Croix Triple Crown victory in 2009. He acknowledged the competitive environment in Puerto Rico, where many skilled jockeys must contend with a limited number of horses and races.
Throughout his long career, Guadalupe endured numerous injuries—from broken bones to a severe accident that left him unconscious and with multiple facial fractures. Remarkably, he continued racing through recovery, embodying resilience and determination.
In his 50s and 60s, Guadalupe scaled back his racing but stayed involved as a steward for several years before returning to galloping and eventually racing again. His son’s ownership of racehorses since 2020 revitalized his career, culminating in race wins penned with the support and encouragement of his family.
Guadalupe rides with care today, cautious about injuries at his advanced age but still maintaining fitness through regular jogging and a healthy lifestyle. His recent wins contribute to his career total of 755 victories in Puerto Rico, a testament to his enduring talent and passion for the sport.
Fan Take: Jessu Guadalupe’s story is an inspiring reminder that passion and perseverance can transcend age, encouraging both fans and aspiring jockeys to never give up. His remarkable career longevity enriches the sport by showcasing the depth of dedication behind every race and the enduring spirit of horse racing.
