At the age of 33, Jim Gregory replaced Imlach as the Leafs' General Manager and he hired former Leaf player John McLellan as his head coach. It was a positive step forward. Gregory had moved up in the Leaf organization having had successful stints as coach and manager of the Toronto Marlies. McLellan had been coaching the Leaf affiliate in Tulsa. The first season after the Imlach era was a learning curve for both the rookie coach and general manager as the Leafs finished out of the playoffs. On March 3, 1970, Gregory traded Leaf legend, Tim Horton, to Rangers in exchange for future considerations which turned out to be Denis Dupere. Horton had played 20 seasons for the Leafs and began a long-term trend where Leaf stars were peddled off to finish their career elsewhere as part of a Leaf rebuild. At one point in the season, injuries to goaltenders forced the Maple Leafs to use an emergency call up from the Senior A Orillia Terriers. That goalie was Gerry McNamara who would play a more important role in frustrating Leaf fans in the future.
As a result of their low finish, the Leafs were able to draft a young centremen from the London Knights whose hero was Jean Beliveau of the Montreal Canadiens. With their first pick (8th overall), the Leafs selected Darryl Sittler who would prove to be one of the greatest Maple Leafs in the history of the Toronto hockey club.
That season Bobby Orr became the first defenceman in NHL history to win the NHL scoring championship. He did it by setting a new record for assists with 87 and totalling 120 points.
It was strange season because both Canadian teams missed the playoffs. The circumstances surrounding Montreal's 5th place finish were extremely bizzare. Entering their last games of the regular season, the New York Rangers were two points behind the Montreal Canadiens for the final playoff spot. A New York victory and a Montreal loss would have left them tied in points, but the Canadiens had a five-goal advantage in the "goals for" category. In their second-last game, the Detroit Red Wings had clinched a playoff spot and many of their players went out celebrating after the game, despite the fact that they were scheduled to face New York the next day to finish the season. Several Detroit players still had hangovers when they took to the ice against the Rangers.
The Rangers managed 65 shots on Detroit goalie Roger Crozier to amass a 9-3 lead early in the third period. Looking for even more goals, Coach Emile Francis repeatedly pulled goalie Ed Giacomin for the extra attacker though this failed to add to the Rangers' tally and the game ended 9-5. New York now had equal points with Montreal and had four more goals for the season. The Canadiens played the Chicago Black Hawks in their final game. But Chicago was playing for first place in the division. With nearly nine minutes left in the third period and down 5-2 to the Hawks, the Canadiens would make the playoffs if they scored three more goals regardless of the game's outcome, so Coach Claude Ruel pulled his goaltender for the extra attacker. Montreal failed to score while Chicago scored five times into the empty Montreal net, to win 10–2. The Canadiens, ending the season with two goals behind the Rangers, were out of the playoffs.
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