The 2026 edition of the highly anticipated Leeward Islands Calypso Monarch competition wrapped up on a high note last night, with Montserrat’s own De Bear emerging victorious over a field of top-tier performers from across the Caribbean subregion. Held as a headline feature of the annual Anguilla Summer Festival, the contest brought together the most celebrated calypso artists from Leeward Islands nations and territories, each vying for the region’s most prestigious calypso title.
After a night of dynamic performances that highlighted the rich cultural heritage and creative prowess of regional calypso, De Bear’s standout set earned him the top spot. Event organizers characterized his winning showcase as a high-energy, electrifying display that encapsulated the soul of modern calypso while honoring its traditional roots, captivating both the live audience and the panel of competition judges.
Following De Bear in the final rankings, Queen Roxxy, representing host island Anguilla, claimed the first runner-up title. King Young Destroyer from Antigua and Barbuda rounded out the top three, securing the second runner-up position after his own memorable performance.
In post-competition remarks, event organizers extended congratulations to all placed winners and every participating calypsonian who stepped onto the stage to represent their home islands. They emphasized that the 2026 contest served as a powerful reminder that the art of calypso remains an enduring, dynamic, and vibrant cultural force across the entire Leeward Islands region, connecting communities through shared musical tradition.
Organizers also confirmed that the beloved regional competition will take a one-year break and is scheduled to return for its next installment in 2027, where a new crop of calypso talent will once again compete for the coveted monarch title.