Montserrat’s De Bear Reigns Supreme Again at The Leeward Islands Calypso Monarch Competition in Anguilla

THE VALLEY, ANGUILLA — Montserrat’s legendary calypsonian, De Bear, has once again proven his dominance on the regional stage by capturing the prestigious Leeward Islands Calypso Monarch title in Anguilla with a commanding performance.

Delivering a masterclass in commentary, lyricism, and stage presence, De Bear thrilled both the judges and the packed audience, amassing a massive total of 866 points to secure the coveted crown. His victory marks another historic milestone in his illustrious calypso career.

Anguilla’s own Roxxy delivered a sensational performance to claim the 1st Runner-Up position with 784 points, keeping the home crowd energised throughout the night. Antigua’s King Destroyer rounded out the top podium spots as 2nd Runner-Up, putting on an exceptional display to score 746 points.

Organisers, fans, and regional delegates extended warm congratulations to De Bear and all participating monarchs for elevating the art form and delivering a night of high-calibre Caribbean culture and musical excellence.

OFFICIAL RESULTS & PODIUM FINISHERS
Winner (Monarch): De Bear (Montserrat) — 866 points

1st Runner-Up: Roxxy (Anguilla) — 784 points

2nd Runner-Up: King Destroyer (Antigua) — 746 points