first team to approach Kennedy was the NHL's Montreal Canadiens, although for Kennedy "It was a boyhood dream to play for Toronto." Dinty Moore, also of Port Colborne, brought Kennedy to the attention Montreal General Manager Tommy Gorman and Kennedy was put on their negotiation list. In the fall of 1942, Montreal contacted the sixteen-year-old about joining the Canadiens. Kennedy's mother was wary of a career in hockey for her son as he was also headed towards studying business at the University of Western Ontario. She agreed to let her son attend the training camp when Montreal scout Dinty Moore assured her Ted was going to receive a good education at Montreal's prestigious Lower Canada College and they were going to cover the cost. Upon arriving in Montreal, foreshadowing future troubles, Kennedy discovered there was no one from the Canadiens to greet him at the train. The teenager was left to his own devices to check into a hotel and make his way around the new city. Then later, as he tried to combine hockey and school, he became concerned his studies were suffering and approached Canadien management to ask if they could find him accommodation closer to the school. He felt they were unresponsive and he soon became disillusioned with the experience in Montreal. After three weeks in Montreal he was feeling homesick and upon completing spring training with the Montreal Royals, he returned to Port Colborne in mid-November. Back home, Kennedy played with the Port Colborne Sailors of the OHA Sr. league for the 1942–43 hockey season. The Port Colborne coach was former NHL star and Hall of Fame inductee Nels Stewart who had been hired in November. Stewart became a mentor to Kennedy, working on his playmaking skills. Kennedy credits Stewart with teaching him how to "operate in front of the net". Kennedy finished the season second in the league, only one point behind scoring champion, Dillon Brady of Hamilton. It was during this time that Kennedy debuted as a player at Maple Leaf Gardens. OHA senior teams played at the Gardens on Friday evenings and this included Kennedy and the Port Colborne Sailors. At the end of the season, in early February 1943, in spite of his having abandoned the Royals, Montreal scout Gus Ogilvie was sent to induce Kennedy to sign a contract with the promise that if he signed, he would finish the season