After five years in the Detroit organization, The Windsor Star's Jim McKay reported on July 6, 1985 that Smith had turned down a one-year contract offer to test the free-agent market. Signed instead by Toronto for two years, "Motor City Smitty", as he was nicknamed by then Leafs' radio man Bill Waters, enjoyed his most productive years on hockey's biggest stage, Maple Leaf Gardens. During the 1985–86 season, Smith registered a career NHL high 17 assists to go along with his five goals over 42 games. As reported by Rick Fraser of The Toronto Star on March 19, 1986, Smith was nominated for the Bill Masterton Memorial Trophy, awarded annually to the NHL player best exemplifying perseverance, sportsmanship, and dedication to the game. He also had an excellent playoff showing, scoring twice (one of which involved a lesson in geometry as he shot from the corner, banking the puck off St. Louis Blues goaltender Greg Millen's pads and into the net for Toronto's only goal in the game seven Norris Final 2-1 loss) and adding an assist in six post-season games.