Community Mourns Loss of Kelly “Pupa Kelly” Charleswell

Kelly Charleswell helps open the St. Thomas Carnival Village, which was named in his honor. (Photo by Michele L. Weichman)

Honored twice this year for his musical contributions to the territory, Kelly “Pupa Kelly” Charleswell was a “pillar whose legacy will continue to live on,” officials said upon Charlewell’s passing this week.

“Pupa Kelly was a beacon of light, love, and excellence for our beloved home,” Tourism Commissioner Joseph Boschulte said in a statement Thursday. The V.I. Division of Festivals recently named the St. Thomas Carnival Village in Charleswell’s honor and recognized his work as a teacher, talented guitarist and musician.

Charleswell studied classical trombone at the University of the Virgin Islands, but guitar was his first love. He played with the Puerto Rico Symphony, Eartha Kitt (the original Cat Woman), Milo’s Kings, Eddie & the Movements, and other iconic bands. He’s best known for singing and playing guitar with the Awesome Jam Band and teaching music at Joseph Gomez Elementary School.

In April, he was also honored during a perma-plaque presentation at the V.I. Legislature. Sen. Donna Frett-Gregory, who sponsored the bill recognizing Charleswell, said during the ceremony that he had “spent decades creating music that uplifts spirits and ignites crowds” and inspired future generations.

“We send our deepest condolences to the entire Charleswell Family and everyone jointly mourning this great loss,” Boschulte added in his statement.