Miff Mole was born in Roosevelt, New York. He became one of the most virtuosic of early jazz trombonists, and perhaps did more to expand the role of the trombone beyond the early New Orleans "tailgate" style than any other musician before Jack Teagarden. He recorded prolifically in New York City in the 1920s and 1930s, often in the company of trumpeter Red Nichols. He played with the bands of Nichols, Paul Whiteman, the Original Memphis Five, the radio orchestras of WOR and NBC, and led his own group, often called "Miff Mole and his Little Molers", in addition to playing and recording with numerous pick-up groups.
In the early 1940s he was a member of Benny Goodman's band. Mole then returned to the small jazz combo format, being a regular for many years at Nick's in Manhattan, where he played with Pee Wee Russell, Muggsy Spanier, Baby Dodds, and other jazz notables.
Miff Mole died in New York City.