Montserrat’s De Bear takes the Leeward Islands Calypso Monarch 2026 crown
De Bear from Montserrat has been crowned Leeward Islands Calypso Monarch 2026 following a lively night of competition in Anguilla.… The post Montserrat’s De Bear takes the Leeward Islands Calypso Monarch 2026 crown appeared first on Anguilla Focus | News.
Black News 
De Bear from Montserrat has been crowned Leeward Islands Calypso Monarch 2026 following a lively night of competition in Anguilla.
The regional event that brought performers from across the region to the stage at the Landsome Bowl Cultural Centre took place on 8 August.
In an online statement, Jayesh Sadhwani, marketing and communications coordinator at Montserrat Arts Council, said: “This victory is a win, not only for De Bear but for Montserrat.
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“Bear continues to set the standard across the Caribbean stage, proving time and time again why he remains a master of the art form.
“It is vital that we capitalise on his knowledge and ensure it is passed on to inspire and equip the next generation.
“We are extremely proud of him and look forward to his continued participation in both the local and regional competitions.”
Anguilla’s recently crowned Senior Calypso Monarch 2026, Queen Roxxy, finished as first runner-up while Antigua and Barbuda’s King Young Destroyer placed second runner-up.
In a Facebook post, Queen Roxxy said she is grateful, humbled and proud to stand among the best from across the Leeward Islands and walk away first runner-up.
“At some point, consistency has to speak for itself. You don’t build a journey of 21 crowns by accident. You don’t keep showing up, evolving, competing and placing across different stages by being a fluke,” she said.
“But I’ve learned that I don’t have to fight every opinion. My work will speak. My performances will speak and my record will speak volumes.”
Queen Roxxy thanked those who had supported and encouraged her throughout the competition, saying she was honoured to represent Anguilla.
“I’ll continue to rise above the noise, remain humble, keep evolving and allow the Almighty to direct my path,” she said.
The competition was part of the festivities during this year’s two-week-long Anguilla Summer Festival which celebrates the island’s cultural heritage and musical talent.
The festival team congratulated the winners and all of the participating calypsonians, saying they represented their islands with “pride, passion and exceptional talent”.
“You made the stage come alive and proved once again that Calypso across the Leeward Islands is strong and thriving,” they wrote in a Facebook post.
The organisers said the competition was “nothing short of amazing, electrifying, and spectacular”.
“The incredible talent from across the region was on full display, with every contender giving their all in an unforgettable calypso showdown,” they added.
De Bear takes the title from Ge’Eve Phillip from Antigua and Barbuda who won the title in 2025.
The festival team said they look forward to welcoming participants back for the Leeward Islands Calypso Monarch Competition 2027.
See the full schedule of the Anguilla Summer Festival events here.
The post Montserrat’s De Bear takes the Leeward Islands Calypso Monarch 2026 crown appeared first on Anguilla Focus | News.
