The Boston Bruins were the favourites to beat the banged-up Toronto Maple Leafs that spring in the Stanley Cup semi-finals but (retroactive spoiler alert) that’s not what happened: the Leafs won. It was early April in 1933. Four of the five games in the series the teams played went into overtime, including the famous last one, which continued on at Maple Leaf Gardens 164 minutes and 46 seconds before it finally came to end, at ten to two on a Tuesday morning, when Boston superstar Eddie Shore made a mistake and the Leafs’ Ken Doraty took a pass and plunked an ankle-high shot past Tiny Thompson.

Toronto 1, Boston 0.

This was, at the time, the longest game in NHL history. The crowd of 14,539 also registered as the biggest crowd in NHL and Canadian history to that date. A new overtime mark — the one that stands to this day — was set just a few seasons later, when the Detroit Red Wings outlasted the Montreal Maroons in March of 1936. (Lorne Chabot was Toronto’s winning goaltender in 1933; in that record-setting ’36 game, he was on the losing end for Montreal.)

Toronto’s reward 91 years ago was joy, no doubt, and relief — for sure — but not much rest: within hours of dismissing the Bruins, the Leafs were boarding a chartered train and tracking down to New York to get the Stanley Cup Final underway against the Rangers.

As for Shore, he did what you do when your season comes to an abrupt end in Toronto in the middle of the night: he headed for the farm.

“Boys, you deserved that one,” Leaf managing director Conn Smythe told his team in the aftermath, “you kept coming and coming and coming.”

 

Doraty was 27 that year, a third-line right winger who can fairly be described as a fringe player — earlier that season the Leafs had demoted him to the IHL Syracuse Stars because he was considered too small to stand the pace of the NHL. But the man summoned to replace him, Dave Downie, didn’t work out, so Doraty was recalled. He was not large, it’s true: 5’7” and (as Baz O’Meara of the Montreal Star put it) “128 pounds soaking wet” were his specs.

A son of Stittsville, Ontario, he spent much of his life, hockey-focussed and otherwise, in Saskatchewan. With the Leafs in 1933 he was — like coach Irvin and teammates Andy Blair and King Clancy — living in the Royal York Hotel, paying (he later recalled) $1.10 a night for his room — about $25 in 2024 dollars. (Doraty’s salary that hockey season was $3,300 — about $74,000 or so in today-money.)

Boston did score a goal in the third period, by way of defenceman Alex Smith, but referee Odie Cleghorn said he’d already blown the play dead. The goaltenders, Thompson and Chabot, went on stopping everything that came their way. The NHL didn’t keep a record of shots on goal at that time, but some newspapers did, and while the puckstopping that went on that night may not constitute an official record, it deserves its due: Chabot deterred 93 shots on the night, Thompson 114.

 

As the game clocked on, later and later, the fans sagged along with the players. “The ice was about gone,” a Boston paper recorded.

Boston Globe writer Victor Jones maybe put it best: “It wasn’t hockey after the first hour of overtime, but it was Homeric nevertheless.”

After the fifth overtime, the restart was delayed a further 20 minutes as officials considered their options. Bruins coach manager Art Ross thought the teams should flip a coin to decide the outcome, and Smythe agreed. NHL president Frank Calder was on hand: he didn’t like the idea. Smythe suggested they should replay the game. Calder’s idea was to play on with no goaltenders, but neither Ross nor Smythe wanted to do that. So they continued into a sixth overtime.

The Daily Boston Globe: “Eddie Shore had the puck just inside his blue line and was wearily trying to get up steam for another trip down the ice.” Blair of the Leafs intercepted him —

 “the long-legged pokechecker.” He passed to Doraty, who was on his right, coasting, he and beat Tiny Thompson with a sharply angled forehander into the far corner.

The Toronto papers, as might be expected, made more hay. Here’s Lou Marsh, from the Daily Star:

The goat of the sensational upset is the greatest hockey player of them all … Eddie Shore … highest paid and most feared foeman in all hockey … the pride of Boston … of the Great West … and of all Canada, for that matter … wonder man of hockey.

That is the irony of fate!

Lady luck kisses the lowly and turns her back on the mighty!

And etcetera. Marsh eventually gets to the goal itself, relishing every moment, giddied, too, maybe, from watching all that hockey:

Shore, weak and weary from a terrific effort, gets the puck down at his own end on a despairing Leaf shot from mid-ice … circles and dodges to and from … looking for a place to break through as the spearhead of another of Boston’s power thrusts.

Shore weaves to and fro behind his own blue line trying to dodge that long-armed, long-legged, mid-ice checking limpet, Andy Blair. Suddenly Blair reaches out with a stick that seems as long as a fishing-pole … hooks the puck away just inside the blue line. Down the right boards comes the smallest man on the ice … the lightest and tiniest man in that grim struggle … scuttering and hopping along like a little bow-legged terrier. Blair shoots the puck back of the leg weary Shore as Doraty comes chop, chopping in like a man with club feet … he isn’t even a good free skate … but he gets there … strongest man on the ice at the moment.

Doraty picks the puck up.

Doraty shoots!

Doraty scores!! He scores!!!

Pandemonium. Shore’s head dropped. “Slowly and idly batted loose pieces of paper to and fro and then climbed wearily over the boards and staggered to the dressing room.”

All over. The Leafs caught their train to New York and were out on the ice at Madison Square Garden that same night — losing by a score of 5-1 to Lester Patrick’s Rangers. “Ten minutes of dazzling speed and they were ice-drunk,” was how one wire service summed it up.

“What could you expect from a team barely out of 164 minutes of play,” wondered Conn Smythe.

The game was over on this night by 10.45 p.m. By 11.30, the Leafs were back on the train and headed home for Toronto. The next three games played out at Maple Leaf Gardens, where it didn’t end well for the Leafs, with the Rangers taking the series 3-1 and captain Bill Cook collecting the Stanley Cup from Frank Calder.