
Keithroy “De Bear” Morson wins 2026 Leeward Islands Calypso Monarch Competition
Antigua and Barbuda’s King Young Destroyer secured a third-place finish in the 2026 Leeward Islands Calypso Monarch Competition, placing second runner-up in the regional showdown held in the early hours of Sunday.
Montserrat’s Keithroy “De Bear” Morson emerged as the 2026 Leeward Islands Calypso Monarch, delivering two commanding performances to capture his fourth regional crown.
De Bear amassed 866 points with his renditions of “Gi Dem Licks” and “When Will We Learn,” comfortably securing the top position.
The victory adds another title to the Montserrat calypsonian’s impressive record in the regional competition. He previously won the Leeward Islands crown in 2007, 2012 and 2023.
Anguilla’s Roxxy claimed the first runner-up position with 784 points, while King Young Destroyer represented Antigua and Barbuda strongly, finishing with 746 points to take second runner-up.
The annual competition brought together some of the region’s leading calypsonians, with representatives from St. Kitts, the United States Virgin Islands, Nevis, St. Maarten, the British Virgin Islands, Antigua and Barbuda, Anguilla and host island Montserrat competing for the coveted title.
King Young Destroyer’s podium finish ensured Antigua and Barbuda remained among the top performers in one of the Leeward Islands’ major regional calypso competitions.





Huhhhhh wasn’t the competition held in Anguilla?
Congratulations