In a stunning debut that captivated the Caribbean racing community, Jamaican architect and businesswoman Isiaa Madden secured a spectacular victory in the prestigious Supreme Ventures Mouttet Mile invitational at Caymanas Park. Her American-bred colt Rideallday delivered a breathtaking performance, overcoming 5-2 odds to claim the US$300,000 prize—the largest purse in English-speaking Caribbean racing.
The three-year-old grey/roan colt, under the expert training of legendary Philip Feanny and ridden by internationally acclaimed jockey Javier Castellano, produced a jaw-dropping stretch run to triumph by an impressive nine-length margin. Clocking in at 1:36.40, Rideallday’s victory was characterized by Madden as ‘nothing short of epic’ following a race that saw the colt initially fall behind before mounting an extraordinary comeback.
Madden, a first-time visitor to the racetrack, expressed equal measures of shock and exhilaration following her unexpected triumph. ‘I was asked to join the racing fraternity, and I took a leap, and I’m so glad I did,’ she told the Jamaica Observer, acknowledging the potential significance of her victory for women in the male-dominated sport.
Beyond the racetrack, Madden carries a distinguished 90-year family legacy through Madden’s Funeral Home, while simultaneously establishing herself as one of Jamaica’s most accomplished architects. Her portfolio includes major Caribbean developments such as RIU, Hyatt, and Half Moon properties, with her most ambitious project—The Pinnacle—set to become Jamaica’s tallest residential estate. Her professional excellence has earned her the Howard University IMPACT Award, recognizing both her architectural achievements and community leadership.
The Mouttet Mile’s electrifying atmosphere and dramatic finish cemented its status as a marquee regional event, while Madden’s victory marked a significant breakthrough in another traditionally male-dominated arena for the multifaceted business leader.