I grew up a Leafs fan and still consider them to be my favourite team — although that means a lot less to me at age 57 than it did when I was 17 … or 7! It’s been a long time since I would say I’ve bled blue and white. It was probably in 1989 (I’d have been 25 at the time) when I made my peace with the fact that the Montreal Canadiens were actually the greatest franchise in hockey history. (Though I’ve yet to make similar peace with baseball and the New York Yankees, whom I still despise!)

So, it’s only with a sense of history — not jealousy — that I consider the Canadiens’ amazing run through the playoffs so far this summer. What’s going to happen next, starting tonight against Tampa Bay? I don’t really like the idea of watching hockey in June, never mind July, but I’m too curious to turn away now!

Who are the most unlikely Stanley Cup champions in NHL history? Probably the 1937–38 Chicago Black Hawks. With a regular-season record of only 14-25-9 in a 48-game season, Chicago barely squeaked into the playoff but then upset the Canadiens, the New York Americans, and the Maple Leafs to win the Cup that spring. While 14 other sub-.500 teams have reached the Final (none since 1991), the only one to win the Stanley Cup was Toronto in 1948-49. The Leafs’ record was 22-25-13 that year, but they had won the Cup in each of the two previous springs, and almost seemed bored by the regular-season before coming to life in the playoffs.

“Anybody who knew us, knew the Leafs were much better than we showed.…” said Howie Meeker in his 1994 autobiography Golly Gee It’s Me. “We weren’t a below .500 club really. Anybody who considered us that was way out of their minds.”

Although the NHL likes to present Montreal’s record of 24-21-11 as if it’s actually over .500, overtime and shootout losses can distort what’s really a loss these days. Still, the Canadiens finished 18th in the league’s overall standings! Given that only 16 of the NHL’s 31 teams (soon to be 32) make the playoffs, there were two teams this year that didn’t qualify in their own divisions despite having better records than Montreal did. It’s kind of crazy that they’ve reach the Stanley Cup Final! There are not a lot of underdog stories in the history of this great franchise, but if Montreal pulls it off against the Lightning now, it’ll rank pretty highly among the NHL’s all-time unlikely winners. And pretty much be the most unlikely winner in Canadiens history.

I’m not analytical enough in my watching of hockey to offer any insight into how the Canadiens have done what they’ve done. So, instead, I’m just going to look back at the Montreal teams that have reached the Stanley Cup Finals 36 times now (twice before the NHL was even founded) and won it 24 times (once prior to 1917–18) to see how this year’s team stacks up.

Many people, it seems, are comparing this year’s Montreal team to 1993, which is the last time the Canadiens (or any Canadian team) won the Stanley Cup. But the comparison is only valid in the styles of those two teams. Montreal had 102 points in 1992-93. They were the fifth-best team in the NHL, although only the third best in their own division. Like this year, they fell behind in their first-round matchup (2-0 behind Quebec), but rallied to win. The fact that the fourth-place Buffalo Sabres (86 points) stunningly swept first-place Boston (109 points) certainly helped clear the path to a division title, and the New York Islanders’ shocking upset of the powerful two-time defending champion Pittsburgh Penguins cleared the way to a Conference championship. But once they reached the Stanley Cup Final, Montreal was hardly an underdog against Los Angeles and beat Wayne Gretzky’s Kings pretty easily.

The Canadiens won a record 10 games in overtime during the playoffs that year. It was a pretty remarkable run. As the team’s star goalie Patrick Roy told NHl.com in 2018 on the 25th anniversary of the 1993 Cup win: “The Canadiens didn’t always have the best team but they always had a team that was willing to work hard and put in the effort to win.”

Seven years earlier, in 1986, the Canadiens had also won an unlikely Stanley Cup title. That year’s team still had future Hall of Famers Bob Gainey and Larry Robinson from the 1970s dynasty, but the key playoff performer (as he would be in 1993) was goalie Patrick Roy, then in his rookie season.

The Canadiens were eighth overall in the NHL standings with 87 points (40-33-7) but a long way back of top teams Edmonton (119 points), Philadelphia (110), and Washington (107). A slew of upsets cleared the way for Montreal and Calgary to reach the Finals that year, and though Calgary had 88 points to and finished seventh overall that season, the only thing really surprising about the fact that the Canadiens beat the Flames to win the Cup was that it only took them five games. An unlikely win for sure, but not really an upset by the end. Still, the 1985-86 Canadiens are probably the weakest team in franchise history to win the Stanley Cup, so certainly an underdog story.

When Calgary and Montreal met again three years later in 1989, the Flames were the NHL’s top team with 117 points and the Canadiens were second with 115. Calgary won the Cup that year, winning the finale at the Forum. It marks the only time the Canadiens lost the Stanley Cup on home ice, which was no doubt upsetting … but the series wasn’t an upset.

In terms of Montreal Stanley Cup surprises, 1971 was certainly unexpected. But, really, the biggest shock came in the first round. The Boston Bruins set all sorts of single-season records that year, leading the NHL with 121 points on a record of 57-14-7. Phil Esposito had 76 goals and 152 points. Bobby Orr had 102 assists. The Bruins had won the Stanley Cup the previous year, and they were ever better now. The Canadiens were actually the NHL’s fourth-best team that season with 97 points, but were decidedly the underdog in their quarterfinal series with Boston. Rookie goalie Ken Dryden, and veteran captain Jean Beliveau in his final season, spearheaded a stunning upset. Beating the 28-34-16 Minnesota North Stars in the semifinals was as it should have been. Defeating a star-studded Chicago team that had 107 points in the regular season to win the Stanley Cup was certainly an upset, although not on the scale of beating Boston. But that year’s Montreal roster was loaded with future Hall of Famers who’d mostly won several Stanley Cup titles already. They were, in actual fact, a very good team.

Interestingly, an earlier Montreal Stanley Cup surprise had also come at the expense of a powerhouse Boston team under remarkably similar circumstances. The Bruins won their first Stanley Cup in 1928–29, and followed up with a record-setting season. Boston went 38-5-1 during the 44-game schedule in 1929-30 for an .875 winning percentage that is still the best in NHL history. (In a modern 82-game season, the mark would translate into 70 wins and 144 points!) Eddie Shore was that team’s Bobby Orr, and Cooney Weiland smashed scoring records just as Phil Esposito would later. Boston had not lost two games in a row all season, yet when the Bruins met the underdog Canadiens in the best-of-three Stanley Cup Final, Montreal swept the series. Having Howie Morenz — probably the greatest player of his era — certainly helped. Montreal also had a few other future Hall of Famers and previous Cup winners that time too.

Mostly, though, throughout their history, the Canadiens have been hockey’s most dominant team and their many championships don’t hold a lot of surprises. Nor do their few losses. Read on, if you care to…

The Canadiens won their first Stanley Cup in 1916. Back then, the champions of the National Hockey Association (forerunner to the NHL) played the champions of the Pacific Coast Hockey Association. Because it could take six days to travel across the continent by train, the entire series was played in the East one year and the West the next. Vancouver had so dominated Ottawa in winning the Cup in 1915 that many thought the calibre of play in the PCHA was above that in the NHA. So, perhaps Montreal was considered an underdog against the Portland Rosebuds in 1916. But they did get to play the entire series at home, and the Canadiens won the best-of-five series in five games. If this was an upset, it was only a minor one.

A year later, Montreal visited Seattle for the 1917 Stanley Cup Final. The Metropolitans beat the Canadiens in four games. Seattle’s win may have been a little easier than experts expected, but Montreal’s loss was hardly a shock. Then again, the Canadiens beat the Mets two games to one in an exhibition series in San Francisco a week later, and team owner George Kennedy felt it proved that his Canadiens were better. When the two teams met again in Seattle in 1919, the series was even with two wins and a tie for each team when the final game was cancelled because of The Spanish Flu.

By 1924, it was pretty clear the calibre of play in the NHL was better than that in the western pro leagues. It was also clear that the home team had a pretty strong advantage in these East-West matchups. So the fact that the Canadiens took two straight games from both the Vancouver Maroons and the Calgary Tigers meant the Stanley Cup probably went to the team that deserved it. By the same token, Montreal’s loss to the Victoria Cougars in British Columbia in 1925 can hardly be considered an upset.

After beating Boston in 1930, the Canadiens eliminated the Bruins again in perhaps a minor upset in their semifinal series in 1931. Chicago battled Montreal harder than expected in the Stanley Cup Final, but the Canadiens won the series as expected.

The 13-year gap between Canadiens Cups in 1931 and 1944 was the longest drought in team history prior to the 28 years Montreal has now gone since winning in 1993. The 1943–44 Canadiens had lost fewer players to military service in World War II than other NHL teams. (The number of military deferments due to essential service jobs away from the rink angered other NHL owners, particularly Conn Smythe in Toronto.) Montreal was a dominating 38-7-5 during the 50-game season. They beat Toronto in five games in the semifinals before sweeping Chicago in the Final. No surprises there. The Canadiens were nearly as dominant again in 1944-45, but were stunned by the Maple Leafs in the first round of the playoffs. An upset, for sure … but not in the Stanley Cup Final.

The War was over by the 1945–46 season. Montreal slipped some, but still finished first overall. No playoff upsets this year, as the Canadiens once again needed only nine games to win the Stanley Cup. A year later, Montreal finished on top of the standings again, but a rebuilt, post-War Maple Leafs team beat the Canadiens in a six-game Final for one of the few times in franchise history that an underdog team beat Montreal for a Stanley Cup upset.

Amazingly, the Canadiens reached the Stanley Cup Final for 10 straight years from 1951 through 1960. Montreal’s loss to Toronto in 1951 was as it should be; the Leafs were much stronger that year. Detroit was clearly the better team too when the Red Wings beat the Canadiens in 1952, 1954 and 1955. The biggest shock in Montreal defeating Boston in 1953 was that the Bruins had eliminated Detroit, while the Canadiens were definitely favourites during their record streak of five straight Cup victories when they beat Detroit (1956), Boston (1957, 1958) and Toronto (1959, 1960).

Montreal might have won five in a row again in the late 1960s, winning as they should have against Chicago (1965) and Detroit (1966) and then defeating St. Louis twice after expansion in 1968 and 1969. Only that pesky loss to Toronto in 1967 — which joins 1947 as the only two years the Canadiens reached the Final and then lost when they were definitely the favourite — upset that dynasty. And if 1971 marks one of the rare occasions when Montreal won the Stanley Cup in an underdog role, wins by the Canadiens in 1973, 1976, 1977, 1978 and 1979 stand as one of the most dominating stretches in hockey history.

All in all in Montreal, it’s a pretty remarkable history.

Just because this is a Stanley Cup story about teams from New York and Montreal, don’t go reading into it that I’m predicting the Islanders and Canadiens to reach the Final. (Then again, if it happens to be the two of them facing off against each other two weeks or so from now, remember where you read it!)

No, this is really just an excuse by me to spin a story out of a recent query about Lester Patrick’s sons, Lynn Patrick and Murray (Muzz) Patrick, scratching their names onto the Stanley Cup as kids when they found the trophy in the basement of their family home in Victoria, British Columbia. The questions was, had it happened in 1925 — when Lester’s Victoria Cougars had won it — or in 1928 — after Lester’s New York Rangers won it.

I’d always heard the story as 1925, and though some stories say 1928, the evidence turned out to be highly in favour of the earlier year, when Lester Patrick was the owner, coach, and general manager of the Cougars. Still, that didn’t stop me from doing plenty of poking around into 1928, when it seems extremely unlikely that as the coach and GM of the Rangers, he’d had the chance to bring the Stanley Cup home to Victoria.

Many of you know that Lester Patrick was a main character in the first book I ever wrote, an historical novel called Hockey Night in the Dominion of Canada. So, for me, any chance to read up on old stories about Lester is like reading letters from an old friend. Lester was quite a bit in the news when the Rangers won the Stanley Cup in 1928, so there was no shortage of stories.

The 1928 Stanley Cup Final between the New York Rangers and the Montreal Maroons was played entirely at the Forum in Montreal. (The Rangers, as would often be the case when the NHL playoffs rolled around, had to evacuate Madison Square Garden for the annual appearance of the Ringling Bros. and Barnum & Bailey Circus). After the Rangers won the best-of-five series with a 2–1 victory in the final game on Saturday, April 14, 1928, they brought the Cup back to New York with them. On April 16, the team was paraded “in motor cars, preceded and followed by a special corps of motorcycle cops,” from Madison Square Garden to City Hall, where they met with New York Mayor Jimmy Walker.

“There we sat,” Lester recalled with a laugh in a story in the Vancouver Sun on May 5, 1928, while visiting from Victoria, “with banners strung along the sides, roaring through the traffic jams, lords of the universe for the time, at least. They paraded us to the city hall and back again in one quarter the time ordinary traffic could have done. The boys got a great kick out of that.”

Lester hadn’t had nearly as much fun getting out of the Forum after the Rangers’ victory over the Maroons.

“I had to fight my way through a yelling mob to the bus, 40 minutes after the game had concluded,” Lester said. “It was a very partisan crowd, naturally. They had figured the Maroons were a cinch, and they couldn’t take the defeat gracefully for the moment.”

Indeed, the crowd in Montreal had not been happy.

Heavy favourites over the Rangers, especially with all the games at home, Montrealers had not expected the series to go the limit, and when it did, the Maroons dominated play in game five, outshooting the Rangers 38-14. Still, they were beaten 2-1. The referees certainly didn’t put their whistles away in this one, with plenty of penalties called. But that wasn’t what upset the fans.

Early in the third period, with the Rangers up 1–0 thanks to a Frank Boucher goal late in the first period, the Maroons appeared to tie the score. Their goal was called back, however, because referee Mike Rodden ruled the play was offside. Montreal fans, according to the Gazette in its Monday recap of the game, “vented their ill-feelings against the arbiter by heaving everything that they could pry loose. The ice was littered as it has never been before.”

The Gazette detailed an “odd assortment of articles that was heaved on the ice.” There were pennies according to some sources, and bottles, one of which hit a player, but didn’t hurt him. “Winter hats were mingled with new spring felts,” said the Gazette, and “one young lady hobbled out after the game with only one silver slipper on, the other having been hurled out to the ice.”

It took a cleaning crew seven minutes to clear the mess, and they had “no sooner made the surface playable when a spectator hurled a chair from a box seat, narrowly missing those in front of the promenade.” The game was further delayed while the chair-tosser was removed from the rink.

The delay apparently took some wind out of the sails of the Maroons, and gave the Rangers a chance to catch their breath. With just under five minutes to go, Boucher scored again to up the lead to 2-0, and, despite a late Montreal goal, New York held on for the victory. But the fans weren’t finished being angry. When referee Rodden failed to pass through the lobby of the Forum on his way out (he apparently left quickly, through a side exit), a small mob turned its attention to NHL president Frank Calder instead. Calder was hustled safely into the Forum business office while a group of ushers “quickly terminated the display of rowdyism.” Lester Patrick had either fought his way through that same rowdy crowd in the lobby on his way to the team bus; or else they had taken their anger outside.

Later that evening, the Rangers and the Maroons shared a peaceful meal together at the Windsor Hotel, where the Stanley Cup was presented to the visitors.

Back in New York two days later, after being received by Mayor Walker at City Hall in the afternoon, the Rangers were dined at the apartment of William F. Carey, vice president of Madison Square Garden in the evening. Between engagements, wherever the players went, they were said to have been greeted by admirers all anxious to see the Stanley Cup.

A few days later, Lester Patrick left New York to return home to Victoria. The Stanley Cup stayed behind, being displayed for a few days in the window of the Fifth Avenue jewellers Cartier & Co., who would create a new silver band to add to the trophy to commemorate the Rangers’ first hockey championship.

Well, the Maple Leafs lost. Again. There was still a long way to go, but there will be no Stanley Cup win in Toronto this year. Again. Just like there hasn’t been since 1967. Haven’t even reached the Finals since then. The Leafs haven’t even won a playoff series since 2004. So, Toronto goes on to Year #55 without a Stanley Cup title, which is the longest drought in NHL history, surpassing the 54 years from 1940 to 1994 that the New York Rangers went without.

Still, when it comes to Stanley Cup droughts, the Leafs are a long way from the longest in hockey history. There’s another city that dwarfs even the drought of 71 years (1945 to 2016) the Chicago Cubs had between World Series appearances, and even the 106 years (dating back to 1908) between Cubs victories. That record drought belongs to … Winnipeg.

Sure, the city didn’t even have an NHL team for long stretches of time, but no team from the Manitoba capital has even played for the Stanley Cup since March of 1908, when (coincidentally) the Winnipeg Maple Leafs were crushed 11-5 and 9-3 by the Montreal Wanderers in a best-of-three-series. The Winnipeg Victorias were Stanley Cup champions in 1896 and 1901, and in that early challenge era when the prized trophy was open to leagues all across the country, they last won it in a successful title defense in late January of 1902. The Victorias defeated the Toronto Wellingtons. That 1902 series marks the first time a Toronto team ever played for the Stanley Cup and the last time a Winnipeg team ever won it. And with the Leafs loss to the Canadiens, it continues to mark the only time that teams representing Toronto and Winnipeg have met in a playoff at hockey’s highest level.

Back at the turn-of-the-20th-century, Winnipeg was a major hockey hotbed. Second only to Montreal. Toronto had plenty of teams then, but the caliber of play in the Ontario Hockey Association was considered weaker than that of Manitoba and Quebec. (Ottawa played in the otherwise Quebec-based Canadian Amateur Hockey League.) Still, the Toronto Wellingtons were senior champions of the OHA in 1900 and 1901, and local backers of the team liked their chances against the Victorias.

Fans elsewhere felt otherwise.

“The Toronto press is still heaping honors on the Wellingtons at the rate of several columns per day and the Stanley Cup is all but on exhibition in the Queen City,” mocked the Ottawa Citizen on January 18, 1902. “There is going to be an unhappy period for those (Toronto) boosters when the Tin Dukes get up against real hockey players in Winnipeg.” (The “Tin Dukes” crack was a shot at the team’s nickname — the Iron Dukes — from the Duke of Wellington for whom they were named.)

Many hockey players — indeed, many athletes in all sports — in this era of amateurism came from well-off families. The Victorias were mainly the sons of Winnipeg’s business elite, with many prominent citizens among their backers. In Toronto, most of the Wellingtons worked in banks or for insurance companies. The OHA was the largest hockey league in the country and rigidly enforced the amateur code, so having money certainly helped! The OHA also seemed more determined than other provincial leagues to maintain a gentlemanly style of play, which, sadly, didn’t help from a competitive standpoint.

In these early days, the need for natural ice meant hockey seasons only stretched from late December to mid March. Train travel meant leagues had to be fairly local, so in order to make the Stanley Cup available to teams all across Canada, the senior champions of any recognized provincial association were able to challenge the current Cup champion. Games could take place before the season, after the season, and even right in the middle of a season. Hence the scheduling of the games in Winnipeg between the Victorias and the Wellingtons for January 21 and 23, with a third game, if necessary, on the 25th. When the Victorias requested that the Stanley Cup series be played later in January, the Wellingtons objected because the bankers on their team had to get back to Toronto in time to balance their books for the first of February.

Obviously, this was a different time … but hockey and the Stanley Cup were hugely popular!

There was, of course, no television or radio in those days, but it was already common for people to meet in public places to listen to someone read out play-by-play reports sent from rinkside by telegraph to newspapers, or for fans to make telephone calls to those newspapers’ offices for score updates. When the Wellingtons traveled to Winnipeg, the OHA’s Toronto-based president John Ross Robertson arranged a novel new way for the fans at home to know what happened.

With the time difference from the West, it was thought that final scores from the Stanley Cup games would be received by telegraph around 11 o’clock or 11:30 at night. When they were, the Toronto Railway Company would blow its big whistle to signal the results: two blasts for a win by the Wellingtons; three would mean victory for the Victorias.

Though few people outside of Toronto gave the Wellingtons a chance in Winnipeg, they surprised their critics by keeping the games close and playing pretty good hockey. Still, the Victorias took the January 21 game 5-3 and won the second game by the same score two nights later, giving Winnipeg a sweep of the series. “We played as hard as we ever played in our lives,” said Wellingtons captain George McKay, “but the checking … was much harder than we were accustomed to. It was fierce.” The players on the Victorias were also said to be faster skaters.

Despite losing their Stanley Cup series, the Wellingtons returned to Toronto and would end the 1901–02 season with their third straight OHA championship. They would win the title again the next year, but passed on another Stanley Cup challenge and withdrew from hockey suddenly and surprisingly just prior to the 1903-04 season.

As for the Victorias, playing a short four-game season in Manitoba against their only senior rival, the Winnipeg Hockey Club, the team went 4-and-0 to win its its tenth consecutive provincial championship in 1902. But after defeating Toronto in January, the Victorias lost the Stanley Cup to the Montreal Hockey Club from the Montreal Amateur Athletic Association that March.

So, while the Maple Leafs are going on to 55 years without the Stanley Cup, the Jets are looking to win Winnipeg’s first in 119 years.