Montserrat's Keithroy "De Bear" Morson is presented the winner's trophy by committee chairperson Katrina Richardson.
On a warm Saturday night in The Valley, Montserrat’s most decorated calypsonian proved he’s still at his peak.
Three years after he delivered the island’s first Leeward Islands calypso title, Keithroy “De Bear” Morson duplicated the feat, scoring a lopsided victory in Anguilla for the 2026 crown. He accumulated 866 points, a whopping 82 more than first runner-up and local favorite Roxanne “Queen Roxxy” Webster. Second runner-up was Leston “Young Destroyer” Jacobs of Antigua & Barbuda, who earned 746 points.
“This crown was more about answering whether I could do it again,” said De Bear, adding that he wanted to “solidify” his historic 2023 Leewards victory for Montserrat. “I was fulfilling a request.”
In the first round, De Bear sang When Will We Learn, a song he first performed in 2022 that stressed the importance of Caribbean unity and cooperation. He then closed the show with Give Dem Licks, lashing out (literally) at any detractors who feel he’s past his prime. De Bear sang last (No. 8) in both rounds, giving him a headliner appeal.
After claiming his record fifth Leewards crown and performing Give Dem Licks one final time, De Bear – who earned EC $10,000 – thanked the Landsome Bowl audience and then asked: “Do you think it’s time for me to retire?”
When the crowd responded with an emphatic “No!” he said, chuckling: “Oh Lord, ayu a go kill dis old man ya.”
De Bear belts out the song “Give Dem Licks” on Saturday, August 8, 2026 at Landsome Bowl in The Valley, Anguilla.
RE-WRITING HISTORY
De Bear reconstructed the lyrics of both songs, especially Give Dem Licks, to make them more appealing and appropriate for the Anguilla crowd. And he didn’t miss a beat. His ability to adjust and improvise gave him a distinct advantage over his opponents.
De Bear said his first-round performance of When Will We Learn was challenging.
“It’s a very difficult song and it almost knocked the wind out of me,” he said. “In the third verse I got tired and wasn’t sure I could do the fourth verse. So I had to pace myself.”
Once he crossed that hurdle, De Bear said the scathing, uptempo Give Dem Licks was easy because he was in his element. “Now that song is me,” he said.
The victory capped a whirlwind two weeks for De Bear, who performed at Montserrat Festival UK in London on July 18 then sang as a guest artist during Antigua’s calypso monarch show July 31 before heading to Anguilla.
De Bear celebrates with Adena Johnson, his backup singer and cousin.
LARGE FOLLOWING
A few days before the show, De Bear told Radio Montserrat that he expected strong support in Anguilla, where he has performed for two decades. The crowd Saturday night included a small contingent of Montserratians.
“I have a large following in Anguilla,” De Bear said. “When I walk into the bandhouse the whole place lifts up and everybody runs in to see what’s happening.”
Calypso committee chairperson Katrina Richardson said she was pleased with the show.
“The turnout was reasonable and the calypsonians were well-received,” she said, adding that she felt the crowd was happy with the judges’ final decision despite Roxxy falling short. “You saw it in their actions and their responses.”
The panel of five judges included two from Anguilla and three from around the region, including Peter White of Montserrat. Asked if that format was utilized to alleviate any suspicions of judging bias, Richardson said, “Definitely.”
MONTSERRAT CONNECTION
De Bear’s backup singers included cousin Adena Johnson, who sang for all the calypsonians as part of the All-Star Band for the second year in a row.
“It was a challenge because we had to learn 16 songs in just three days,” she said. “But I’m always excited and ecstatic to represent Montserrat.”
Watching her cousin don the oversized winner’s crown was the perfect capper.
“De Bear is an exceptional calypsonian,” she said. “For me, De Bear represents a standard of excellence, and I hope this victory inspires our calypsonians to aspire to the same level.”
PAYING IT FORWARD
Asked about his career going forward, De Bear said his focus is no longer about proving whom he can defeat on stage, but how he can assist the next generation of calypsonians in Montserrat.
“I’m hoping Montserrat doesn’t make the same mistake they made with Arrow,” he said. “They got caught up in his legacy and didn’t look for a replacement. They cannot wait until I’m taken down by illness or death to look for a prodigy to take over and keep Montserrat on top. We need to help the children coming up, help them write their songs, even if they need help from A.I.”
▪ The other performers were Richie Buntin (U.S. Virgin Islands), Eklund “Officer” Adams (BVI), Edsel “Mighty Yard Fowl” Eusebius (St. Maarten), Tariq “Drewzy” Drew (St. Kitts) and K-Jel “Kairo” Smithen (Nevis). Defending Leewards champion Ge’Eve Phillip of Antigua did not participate due to illness, organizers said.
– Keithroy “De Bear” Morson
Calypso crowns by De Bear (De Voice)
| Year | Event | Songs |
|---|---|---|
| 1985 | Montserrat Jr. Calypso | Slavery (one song) |
| 1992 | Montserrat Festival | Back to Basics & Face The Truth |
| 1993 | Montserrat Pilgrimage | Come Home (one song) |
| 1993 | Montserrat Festival | The Time Has Come & Show Respect |
| 2002 | Antigua Independence | Man Is Dust & Help |
| 2007 | Antigua Carnival | I Say No & Support Party |
| 2007 | Leeward Islands Competition | I Say No & Man Is Dust |
| 2010 | Antigua Carnival | Leopard Come Home & Don’t Sing Bout de Judgment |
| 2011 | Antigua Carnival | Melee For Sale & We Get The Change Ivena |
| 2012 | Antigua Carnival | Time To Take Our Place & Freedom for Mandela |
| 2012 | Leeward Islands Competition | Time To Take Our Place & Freedom for Mandela |
| 2014 | Montserrat Festival | Don’t Forget Your Juliet & Got To Go |
| 2015 | Antigua Carnival | Can’t Stop The Bear & Sing A Different Song |
| 2015 | Leeward Islands Competition | Can’t Stop The Bear & Sing A Different Song |
| 2019 | Antigua Carnival | Let The Master Show You & On A Ray Of Hope |
| 2020 | Montserrat Carnival | By Faith & Call Daddy |
| 2021 | Montserrat Carnival | Let Us Rebuild & Don’t Wake The Bear |
| 2022 | Montserrat Carnival | Hard Like A Diamond & Ah Shoulda |
| 2023 | Leeward Islands Competition | Hard Like A Diamond & Don’t Wake The Bear |
| 2025 | Montserrat Carnival | Come Serve Your Country & Give Dem Licks |
| 2026 | Leeward Islands Competition | When Will We Learn & Give Dem Licks |
Montserrat Notable Regional Titles
| Year | Event | Winner |
| 1951 | Leeward Islands Cricket | Montserrat |
| 1953 | Leeward Islands Cricket | Montserrat |
| 1986 | OECS Calypso Monarch | Justin “Hero” Cassell |
| 1987 | Caribbean Talented Teen | Stacy Richards |
| 1987 | OECS Queen Show | Pauline Wall |
| 1988 | OECS Queen Show | Jemma Neptune |
| 2015 | Caribbean Jaycees Queen | Sharissa Ryan |
| 2023 | Leeward Islands Calypso | Keithroy “De Voice” Morson |
| 2026 | Leeward Islands Calypso | Keithroy “De Bear” Morson |
