Turmoil was always part of an Imlach team and things were no better during the 1968-69 season. In December 1968, Imlach was asked by Maple Leaf President Stafford Smythe to give the coaching job to John McLellan, but Imlach refused and told Smythe to fire him or leave him alone. During the season, Mike Walton walked out on the team, saying he wouldn't play for Imlach again. He returned about a week later. Imlach picked up Brit Selby and Forbes Kennedy late in the season for a playoff drive.
The Leafs finished in 4th place in the East and played the Bruins in the quarterfinals. Toronto did rebound to make the playoffs in the 1968-69 season, but were thoroughly dominated by the ultra aggressive, Bobby Orr-led Boston Bruins and lost in four straight games - the Leafs being humiliated in Boston by 10-0 and 7-0 scores. The Leafs lost 4 straight to the Boston Bruins by a combined score of 24-5. During the series the famous Pat Quinn hit on Bobby Orr took occurred. Quinn was a slow hulking defenseman for the Maple Leafs who caught Orr with his head down and knocked him out. Quinn was assessed a 5 minute major for elbowing on the play, but ultimately referee John Ashley was penalizing him for hitting the game's greatest player, or at least for causing the resulting donnybrook. Forbes Kennedy, playing in what proved to be his last game, was front and center in the aftermath of the hit. When all was said and done he had set NHL records for most penalties in a game (8), most minutes (38 - since bettered), most penalties in a period (6) and most penalty minutes in a period (34). He was also suspended for three games, reportedly for punching a linesman en route to the locker room.
On April 6, 1969, minutes after the embarrassing playoff elimination at the hands of the Bruins, Imlach was fired by the Leafs. He still had a year remaining on his contract, which paid him about $35,000 a year. In the dressing room after the announcement was made, veteran Leafs Johnny Bower and Tim Horton both said they would leave with Imlach (they both returned the following season, although neither would remain with the Leafs for long). Imlach's assistant, Clancy, had previously said that he would walk away if Imlach was fired, but he was persuaded to stay with the team. Jim Gregory was immediately announced as Imlach's replacement as general manager.
Stafford Smythe announced that ‘the Imlach era is over’. And indeed it was for now.
There was also turmoil off ice. The Leafs were controlled by Stafford Smythe, John Bassett and Harold Ballard. Following an RCMP raid at the Gardens in 1968, Smythe was charged with income tax evasion and accused, along with Ballard, of illegally taking money from Maple Leaf Gardens Ltd. to pay for renovations of their houses and other personal expenses. Just before the charges were laid Bassett argued to the Gardens board that Smythe and Ballard should be removed from their posts. On June 26, 1969; Smythe and Ballard were both fired, and Bassett was appointed president of the Gardens.
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