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Born and reared in Milwaukee, Wisconsin, Trimble taught himself the trombone at age five and later became a Wisconsin State champion trombonist. After serving in an Army band during World War II, Kenny played with various bands such as Tex Beneke, Ray Anthony and Glenn Miller prior to joining Welk in 1957. He appeared on the Maestro's weekly television show and toured with the band on their live concert tours for the next twenty-five years. His talents was not limited to the brass section, he also provided vocals in many group numbers that were featured on the show.
Kenny's son, Jimmy, became a professional musician in his own right and also plays the trombone. Trimble's grandson Jon plays the trumpet.