Levinsky played for the Toronto Marlboros juniors and seniors as well at the University of Toronto for a year. Levinsky won the Memorial Cup with the Marlboros in 1929, He debuted with the Toronto Maple Leafs late in the 1930-31 season. "Mine Boy" became a regular the next year and helped the franchise win its first Stanley Cup as the Maple Leafs. He spent two more years with the Leafs before he was traded to the New York Rangers for cash.