Montserrat’s calypso monarch De Bear has won the 2026 Leeward Islands Calypso Monarch Competition, reclaiming the regional crown three years after his previous victory.
In the early hours of Sunday morning, host Fernando Clark of St. Maarten, announced that De Bear topped the competition with 866 points following performances of “Gi Dem Licks” and “When Will We Learn”.
Roxxy of Anguilla secured first runner-up with 784 points, while Antigua’s King Destroyer placed second runner-up with 746 points.
De Bear entered the regional competition as Montserrat’s reigning calypso monarch. His victory marks his fourth Leeward Islands crown, having also captured it in 2007, 2012, and 2023.
He was supported during his performances by backing vocalists who included Montserrat’s Adena Johnson.
Trinidad and Tobago calypsonian Tameika Darius also made a special guest appearance at the event.
The 2026 competition featured representatives from St Kitts, the US Virgin Islands, Nevis, St Maarten, the British Virgin Islands, Antigua and Barbuda, Anguilla and Montserrat.
Results
Winner: De Bear, Montserrat. 866 points
First runner-up: Roxxy, Anguilla. 784 points
Second runner-up: King Destroyer, Antigua. 746 points
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