 On March 3, 1943, Kennedy signed a professional contract with the Toronto Maple Leafs, but management of the Leafs still wished to see Kennedy playing in an NHL game. Late in the 1942 – 43 season, they received permission from Kennedy's mother to take him out of school so he could accompany them on a road trip. He played in two of the final three games of the regular season, but did not continue with them into the playoffs. Making his NHL debut March 7, 1943, against the New York Rangers at Madison Square Garden, he was put on the Leafs' third line on rightwing, instead of his customary centre position, on a line with Bud Poile and Gaye Stewart. He was told by coach Hap Day to simply "stay with your check and keep him from scoring." Kennedy's line scored three goals and he picked up one assist in a 5 – 5 tie. He then picked another assist in the next game in Boston. Kennedy had impressed the Leaf coaches, but his rights were still "officially" owned by the Montreal Canadiens.
