Calypso

Scores of people gathered at the John A. Osborne Airport Monday to welcome home Keithroy “De Bear” Morson, after he secured his 5th crown at the 2026 Leeward Islands Calypso Competition over the weekend. He was met on arrival by a delegation including Deputy Premier Veronica Dorsett-hector, Minister of Agriculture Honourable John P. Osborne, and Parliamentary Secretaries Honourable Crenston Buffonge and Honourable Dwayne Hixon. He was also greeted by a group of young masquerade dancers. Throngs of his supporters gathered outside the arrivals area as the champion calypsonian emerged gripping the trophy in one hand, and waving the Montserrat flag with the crown resting proudly on his head. Speaking on the Breakfast Show, De Bear said the most exciting part for him was representing Montserrat and being an inspiration to others. With his commanding performances of the songs “When Will We Learn” and “Gi Dem Licks”, De Bear outpaced his competitors, amassing a total of 866 points.  Anguilla’s Roxxy claimed first runner up with 784 points while Antigua’s Destroyer was second runner up with 746 points. De Bear, previously won in 2007, 2012, 2015, and 2023. Peter W. A. White served as a judge and while Adena Johnson was a back-up vocalist. The competition featured performers from St Kitts, the US Virgin Islands, Nevis, St Maarten, the British Virgin Islands, Antigua and Barbuda, Anguilla, and Montserrat.