During the early 1940s, Toronto and Montreal played catch, tossing two young players between them. The game ended on September 10, 1943 with Frank Eddolls going to the Canadiens in return for the Maple Leafs keeping Ted “Teeder” Kennedy. It has been called the best trade Toronto ever made, from which they created a dynasty.

Kennedy was born in Humberstone, Ontario, less than two weeks after his father died in a hunting accident. His mother worked at the local hockey arena, where he spent most of his time. From at least the age of 7, when he first saw No. 9 Charlie Conacher, Kennedy was a Maple Leafs fan. He later said, “It was a boyhood dream to play for Toronto.”

However, the first NHL team to show interest was Montreal. In 1942, they invited the 16-year-old to the training camp for their junior team, the Montreal Royals. The scout assured Kennedy’s mother that they would be paying for him to attend Montreal’s prestigious Lower Canada College. From the moment he arrived without anyone from the team to greet him or assist him, Kennedy had bad feelings about continuing with the team. After three weeks, Kennedy grew homesick enough to head home.

Back in Ontario, Kennedy played for the Port Colborne Sailors senior team. Their coach was none other than Nels Stewart, a record-setting NHL goal-scorer (who would be inducted into the Hockey Hall of Fame in 1952). As the season ended in February 1943, a scout negotiated with Kennedy to sign a contract with the Montreal Canadiens. Kennedy declined, explaining, “It wasn’t a bluff for more money, I simply had no intention of going to Montreal.” The scout warned that the only way to turn pro was with the Canadiens. 

Meanwhile, Stewart had other ideas, considering Kennedy “a coming great.” He told the Maple Leafs about his protégé and got him a meeting. On February 28, Kennedy traveled to Toronto, was met at the train station, and by that evening, signed a contract with interim GM Frank Selke. As the youngest player ever to dress for the team, he debuted with the Maple Leafs on March 7 and impressed all of the coaches.

As Kennedy was still “officially” owned by the Canadiens, Toronto had to make a trade to obtain clear rights. Once that was done on September 10, Kennedy spent his inaugural season with the Leafs in 1943-44. Coach Hap Day said at the time, “We know we are giving up a strong defence player to deal with Kennedy, but we won’t be shy of defence material after the war and we do need attack strength now.” Selke said much the same. “We are taking a gamble. We think Kennedy is a coming star.”

On the other end of the trade, Eddolls was actually returning to Montreal. The defenseman grew up in Lachine, Quebec and had an arrangement with the Canadiens while playing in juniors. After his Oshawa Generals won the 1940 Memorial Cup, the Maples Leafs wanted to sign him. On June 7, 1940, Montreal traded Eddolls’s rights to Toronto in return for the rights to Joe Benoit. The following year, Eddolls began playing for the AHL Hershey Bears, but he soon left for military service. The trade happened while he was serving, so he returned home to find himself at the Canadiens’ training camp.

Eddolls remained with the Habs for three partial seasons, winning the Stanley Cup in 1946. He was traded to the New York Rangers in August 1947 and finished out his NHL career there in 1952. On October 8, 1952, Eddolls was actually sold back to Montreal, to serve as playing coach of the AHL Buffalo Bisons. Eddolls had one last NHL hurrah, as coach to the Chicago Blackhawks for the 1954-55 season.

Though the trade has widely been praised as one of Toronto’s best, it came at the cost of a schism in management. At the time, Selke was only covering for GM Conn Smythe, who was serving overseas during the war. As Selke himself said (in 1962), “I told Dick Irvin that the Maple Leafs were desperate for bodies to fill the lineup, and that we could give up the rights to [Frank] Eddolls for the rights to Ted Kennedy. After weeks of negotiation and a lot of hesitation, Gorman and Irvin finally consented to make the trade. Fearing they might change their minds … Happy Day and I completed the transfer of Eddolls to Montreal without taking the time to consult Smythe … [We] received a cable from France ordering us to cancel the deal. It was ignored, and Ted Kennedy developed into as effective a hockey player as the Maple Leafs ever owned. But the deal spelled finis to my usefulness as an assistant to Conn Smythe.”

Smythe was so furious when he returned, in 1946 Selke decided to go to Montreal himself. During Selke’s 18 years managing the Canadiens, they beat Toronto’s dynasty by winning five consecutive championships. Meanwhile, back in Toronto, Smythe ended up praising Kennedy as the “greatest competitor in hockey.”

Kennedy had a Hall-of-Fame career in which he only ever played for Toronto, leading to him being called the “quintessential Maple Leaf.” Coach Day made him into the best faceoff man in the league and earned a reputation for making important goals during playoffs. The Leafs won five championships during his first seven seasons, including three consecutively. Having become captain in 1948, he accepted the Stanley Cup on the third win by telling the crowd, “We must have been an awful strain on you because there were times when even we didn’t think we were going to get into the playoffs. But here we are – and there’s the Cup.” At the end of his career, as something of a lifetime acknowledgement, in 1955 he was awarded the Hart Trophy as league MVP. After a brief return to assist his struggling team, Kennedy retired for good in 1957.

Having worn No. 9 throughout his junior career, Kennedy finally received the prized number in the NHL at the start of the 1946-47 season, when Conacher himself presented the number to him. Thus began Toronto’s tradition of having a player pass down his number to another great player. In 1993, the Leafs retired No. 9 for Kennedy and No. 10 for Syl Apps. Kennedy was inducted into the Hockey Hall of Fame in 1966.

Additional Sources:
In her personal history, Kyle Hurst hated her toe picks and wanted to skate on a hockey team like her brother. With age comes wisdom, and realizing how poorly she skates, she now much prefers watching the professionals. Writing about history for her day job, Kyle enjoys combining her two loves by writing hockey history. She still hates toe picks.

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