The struggles by the Maple Leafs as a team, and by Macoun individually, early in the 1996–97 season led to his name being associated with trade rumours as Toronto contemplated moving one of their older defencemen. He finished the season with Toronto, and remained with the team into 1997–98. On November 8, 1997, Macoun played the 1,000 game of his NHL career, against the Phoenix Coyotes. However, with Toronto situated outside of a playoff spot late in the season, the Maple Leafs traded Macoun to the Detroit Red Wings on March 24, 1998, in exchange for a fourth round selection at the 1998 NHL Entry Draft.