Bester spent parts of 11 seasons in the NHL, beginning in 1983–84. He spent eight years in Toronto, and then was traded to the Detroit Red Wings in 1991. He spent most of his career moving between the NHL and American Hockey League (AHL). In 1992, Bester won a Calder Cup with the Adirondack Red Wings. He was awarded the Jack A. Butterfield Trophy as playoff MVP. Bester made a short return to the NHL after a four-year absence, playing ten games for the Dallas Stars in the mid-1990s.