Best and worst moments from the Maple Leafs-Bruins rivalry

Auston Matthews, Morgan Rielly, John Tavares and Coach Babcock discuss the team's mindset heading into their first round playoffs series against the Boston Bruins.

Because of the tightly contested seven-game playoff series between the Toronto Maple Leafs and Boston Bruins in 2013 and 2018, it is assumed that the pair of Original Six franchises have a hot and full rivalry.

But that actually hasn’t been the case.

Today, let’s run down the highlights from Leafs-Bruins history prior to their last two playoff meetings (and the 2009 Phil Kessel deal, which I’m sure you’re aware of).

Oct. 3, 1958: New Leafs general manager (and coach) Punch Imlach quickly put his imprint on the team with the first in a series of four trades that would add veteran players to complement his up-and-coming young team full of recent graduates from the Toronto Marlboros and St. Michael’s College. This blend would culminate in the Leafs winning four Stanley Cups in the 1960s.

On this day, Imlach added 32-year-old defenceman Allan Stanley from the Boston Bruins in exchange for Jim Morrison.

In a sign of what a different era it was, Stanley found out he had been traded just before practice, but he went out to practice with the Bruins anyway. When he decked a teammate coming down on a rush and other shouted at him to take it easy, he shouted back, “Not anymore — I’m a Toronto Maple Leaf now!”

That season Imlach would also acquire 33-year-old Johnny Bower from the New York Rangers and 32-year-old Bert Olmstead from Montreal. A year later he would add 32-year-old Red Kelly from Detroit.

April 7, 1959: The Leafs won Game 7 of their first-round playoff series with Boston by a 3-2 score, kicking of a sad-sack period for the team. After this playoffs, the Bruins would finish out of the playoffs the next eight consecutive seasons, coming in fifth on two occasions and finishing dead last at sixth the other six times.

But Toronto hasn’t beaten the Bruins in a playoff series since. It’s the longest current drought — 60 years, to be exact — that the Leafs have against any Original Six team.

April 7, 1960: Ironically, exactly one year after eliminating the Bruins in the playoffs, the Leafs were guilty of an “inaction” that would eventually help kick off an era of NHL success for the Bruins.

The Leafs had held the advantage of basically getting first crack at any quality young player that lived in the province of Ontario. That is how they had developed a team that was on the verge of great things that decade. Anthony Gilchrist, a bird-dog scout for the Leafs located in Parry Sound, had written to Punch Imlach in early 1960 advising the team of a young local player named Bobby Orr. He suggested that Imlach take a serious look at the 12-year-old, and also let him know that the boy’s father and grandfather, Doug and Robert, respectively, were diehard Leaf fans.

In what would be his greatest error as a hockey man, Imlach didn’t respond himself. Instead, he passed the note to his chief scout. In a letter dated April 7, 1960, the chief scout thanked Gilchrist for the information, but declined to follow up on Orr, writing that “the boy is a little too young to be put on any list for protection.” He added: “I will keep his name on file and when he gets to be fourteen or fifteen we will contact him and, if he is good enough, I would recommend a hockey scholarship for him here in Toronto.”

The four-paragraph letter ended with a haunting remark: “I hope that some day Bob Orr will be playing for the Toronto Maple Leafs.”

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Jan. 18, 1964: On the way to winning their third consecutive Stanley Cup, the Maple Leafs were worried very little about the Bobby Orr they had allowed to escape from their clutches. Also, while Orr was showcasing his skills with the Bruins’ OHA-affiliate Oshawa Generals, his eventual NHL club was set to finish dead last once again.

On this night, however, the Bruins shut out Toronto by an 11-0 margin. It’s still the most lopsided shutout ever recorded against the Leafs.

June 9, 1965: The old NHL Intra League Draft rarely saw an elite player switch teams. It generally provided a journeyman player from one of the better NHL teams a chance to be claimed by — and get playing time with — one of the weaker NHL teams.

On this day, though, Imlach had a predicament. His top minor-league goaltender was 25-year-old Gerry Cheevers, who had to be protected by the Leafs or he’d become eligible to be claimed. Should Imlach risk exposing one of his two veterans (Johnny Bower, 40, or Terry Sawchuk, 36) in order to protect Cheevers even though many thought it was doubtful that either veteran goaltender would be claimed because of their ages (particularly Bower)?

Initially Imlach tried to sneak Cheevers onto the Leafs’ protected list as a skater (rather than a goaltender). That maneuver was quickly disallowed by NHL president Clarence Campbell. So Imlach decided to be loyal to his veterans and made Cheevers eligible for claim.

The dead-last Bruins quickly claimed Cheevers and add another future Hall of Famer to their roster. Cheevers would be their No. 1 goaltender for their Stanley Cup victories in the 1970s.

Dec. 4, 1966: Having tallied 13 points in his first 18 NHL games, Orr’s rookie seasons was off to a strong start. But his Hall of Fame career would unfortunately be plagued by a number of knee injuries, which all began on this night.

In what wound up being an 8–3 win for Toronto, Leafs defenceman Marcel Pronovost caught Orr (and his knee) with a hard hit as the rookie tried to go around him. Orr would miss seven games.

The Pronovost hit would lead to Orr eventually having his first knee surgery. With the lack of orthopedic knowledge back then, that surgery is blamed for inflicting more damage on the knee than actual repair, leading to Orr’s knee woes becoming an ongoing career reality.

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May 15, 1967: The vivid memories of the Leafs’ last Stanley Cup win over the Montreal Canadiens remain today. But it was their first-round win over the Chicago Blackhawks that was the big upset. Chicago had finished the regular season with 94 points, a healthy 17 points better than the 77 accumulated by second-place Montreal. As such, the Blackhawks were the prohibitive favourites to win the Cup, but still got ousted in six by Toronto.

In a story I had recounted to me by both Bobby Hull and Phil Esposito, the Blackhawks had an end-of-season party a few days after getting eliminated by the Leafs. It was an agitated and disappointed group of players and management that consumed many beverages to try to ease the pain of their upset loss. Phil Esposito had just finished his third full season for the Hawks and had scored more than 20 goals in all three seasons, a very respectable total in those days.

But he hadn’t scored in the series against the Leafs and he felt the wrath of GM Tommy Ivan and coach Billy Reay. The bad feelings were mutual. As Esposito chatted with Hull while consuming beverages, he looked at Ivan and Reay and expressed an expletive-laden opinion about how the team could never win with them in charge. Hull says he was kidding when he suggested Esposito “tell them yourself what you think of them,” but minutes later he watched his young teammate give both bosses a boozy rendition of their shortcomings.

Esposito told me he went to the Hawks’ executive offices the next day hoping to mend fences. Ivan just yelled through his closed office door to his secretary: “Give him his travel money and tell him to get the hell out of here.”

Just a few weeks later, Chicago completed a very one-sided trade, sending Esposito, Ken Hodge and Fred Stanfield to Boston in exchange for Gilles Marotte, Pit Martin and Jack Norris. The cast for the Bruins’ two Stanley Cups in the 1970s was now pretty well complete.

There can be no question that this trade was in many ways a product of the disappointment of that first-round upset versus the Leafs. So in a roundabout way, the Leafs provided yet another big boost to the Bruins roster.

April 6, 1969: This is the day that the Punch Imlach era died. The Leafs were not only swept by Boston in their first-round playoff series — they were humiliated by a total margin of 24 goals to five. It was the first time the Bruins had eliminated the Leafs in the playoffs since 1940, when they won their first-round series in seven games.

The worst of the worst for the Leafs was that first game in Boston that they lost 10-0. While the only Leafs “highlight” from that game seems to be Pat Quinn’s devastating hit on Orr, it was actually a player named Forbes Kennedy who proved to be the side show for the Leafs on that night. In what would be his last NHL game, Kennedy picked up 38 minutes in penalties and incurred a five-game suspension for slugging linesman George Ashley.

Minutes after the fourth and final game of the series ended, Leafs president Stafford Smythe fired Imlach in his coaches’ office by the dressing room.

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March 3, 1972: The Bruins would actually do the Leafs a favour in a trade-deadline-type deal. Jacques Plante had played extremely well in his brief time with the Leafs, and the Bruins acquired him and a third-round draft selection in exchange for goaltender Ed Johnston and a first-round pick in the 1973 Amateur Draft.

The Leafs would use that pick on Ian Turnbull from the Ottawa 67’s. Turnbull would have a very solid career with the Leafs, often paired with another 1973 newcomer — future Hall of Famer Borje Salming.

April 11, 1972: A little over a month after the Plante trade, the Bruins (with the goaltending tandem of ex-Leafs Cheevers and Plante) eliminated the Leafs four games to one in their first-round playoff series. Toronto’s only win came in Game 2 when Jim Harrison (whom the Leafs had acquired a few years earlier from Boston for Wayne Carleton) scored in overtime for a 4–3 Leafs’ win.

The Leafs and Bruins would not meet in another playoff series until 2013.

Feb. 7, 1976: The NHL record that never will be broken was established — the one Wayne Gretzky was always aware of but could never match — as Darryl Sittler recorded his historic 10-point night (six goals, four assists) in an 11–4 win at Maple Leaf Gardens.

Dec. 30, 1989: On the cusp of a new decade, he Leafs staged their largest comeback for a win in their team history. Down 6-1 to the Bruins, the Leafs came back with six unanswered goals to defeat the Bruins 7–6 in overtime. After Mark Osborne had scored the early Leafs goal, the six-goal run was led by two from Eddie Olczyk and singles from Vincent Damphousse, Luke Richardson and Gary Leeman, and the overtime winner by Wendel Clark.

Jan. 3, 1996: In one of the stranger hockey scenarios, rookie Bruins head coach Steve Kasper sat out both Cam Neely and Kevin Stevens for an entire game at Maple Leaf Gardens, which ended in a 4-4 tie.

Kasper was angry with his team’s performance the previous night against Chicago. Both players had no idea as the game unfolded that they would be permanently glued to the bench. Bruins fans and especially Neely himself were outraged by Kasper’s puzzling actions.

Neely would end his Hall of Fame career that season at the age of 31, like Orr a victim of early retirement due to knee woes. He scored 26 goals in 49 games that season.

Kasper would coach just one more season with the Bruins. He later was a member of the Leafs’ front office for a number of years. Although he lives in Boston, Kasper remains an estranged member of the Bruins’ alumni, and will likely remain so as long as Neely is their president.

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