After winning consecutive calypso monarch crowns in Montserrat in 1992 and 1993, De Bear relocated to Antigua and continued his calypso career. He threw himself into the extremely partisan and divisive elements of Antigua politics and sang scathing commentaries each year. He was near-flawless in 2004, pouring his heart out in his two compositions -- I'm Here To Stay, a defiant song proclaiming that Antigua is now his home and his detractors should stop wishing for his departure, and While We Rejoice, a song reminding Antiguans that although there's a new prime minister, the country's problems are far from over. Nonetheless, De Bear finished fourth -- behind winner Ivena, Edimelo and Singing Althea. Though small in stature, De Bear isn't afraid to take on all comers -- "I may be small but my back is strong" he says in I'm Here to Stay. But despite consistent performances each year, he couldn't snare the crown until 2007 with the songs I Say No and Support Party. Just a week later, he traveled to Anguilla to compete in the Leeward Islands Calypso Competition and also won. He again sang I Say No, but for his second song he chose Man Is Dust, which he had recorded some years earlier.