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While winning a championship is tough in any sport, reaching the top of the NHL mountain is uniquely challenging. Not only is hockey a random game — between the ice, the lack of structured plays, and the speed of play, a bad bounce can make all the difference — but there’s a great deal of physical attrition. Whichever team wins the title will have survived 82 regular season games plus a minimum of 16 playoff contests. No wonder winning the Stanley Cup is such a special moment for everyone involved.

Even if lifting Lord Stanley’s chalice is considered one of the toughest feats in sports, there are still some lucky franchises that have accomplished that feat multiple times. Which team is the best of the best, at least when it comes to winning the most Stanley Cups?

Let’s break it down.

T-10. The St. Louis Eagles: 4 Stanley Cups

Even if you’re a diehard NHL fan, you probably haven’t heard of the St. Louis Eagles or their Stanley Cups. That’s probably for a good reason: the franchise didn’t make much of an impact, at least in Missouri.

The club began as the original Ottawa Senators and won four titles in Canada’s capital. The Senators eventually began to struggle, though, and found themselves facing financial difficulty. That facilitated a move to St. Louis, hoping the bigger market would sustain a new generation of success.

In reality, though, that didn’t happen. The St. Louis Eagles took flight in 1934 and only survived a single season. The club was bought by the NHL and folded, with the players being spread around the league.

If nothing else, though, the Eagles live on in the history books.

T-10. The New York Rangers: 4 Stanley Cups

There was a time when New York Rangers fans heard mocking chants of 1940 everywhere they went. While that insult is no longer valid, the Blueshirts still don’t have the greatest championship history.

Most of the club’s success came in the early days of professional hockey. The Rangers lifted the Stanley Cup in 1928, 1933, and 1940. Then, a massive drought began. There are various theories about a curse — some say the Blueshirts desecrated the Stanley Cup — but the result remained the same: postseason success didn’t return to Madison Square Garden.

In 1994, however, that all changed. Despite a dominant regular season, things weren’t easy — a Stephane Matteau goal prevented an untimely end to the campaign — the Rangers ultimately lifted the Stanley Cup.

Success hasn’t returned to MSG since, despite a series of close calls, but that most-recent victory will last a lifetime.

T-10. The New York Islanders: 4 Stanley Cups

Remember how I mentioned the chants of 1940? Many of those came from New York Islanders fans, who saw their team out-achieve the Rangers in a short period of time

The Islanders first took the ice in 1972 and, within a decade, had become the NHL’s dominant franchise. Behind a legendary core of Denis Potvin, Clark Gillies, Brian Trottier, Mike Bossy, Bobby Nystrom, and Billy Smith, the club rattled off an incredibly four-straight Stanley Cup wins in 1980, 1981, 1982, and 1983.

Those victories put them ahead of the Rangers until 1994, when the Blueshirts evened things up at four championships apiece.

Since those early years, the Islanders have endured some incredibly tough times. The memories of the dynasty years, though, will never fade.

T-7. The Pittsburgh Penguins: 5 Stanley Cups

At the risk of resorting to a cliche, Pittsburgh is a good sports town. The Penguins have pulled their weight, bringing five Stanley Cups to the Steel City.

The first two of those titles came in 1991 and 1992, as Mario Lemieux led the club to glory. After some lean years, another star, Sidney Crosby, came to town. He helped the Penguins reach the 2008 Stanley Cup Finals, but the Penguins fell to the Detroit Red Wings. The following year, though, things would be different.

In 2009, Sidney Crosby, Evgeni Malkin, and company lifted the Penguins’ third Stanley Cup. While that was expected to kick-start a dynasty, it took some time to return to the top of the mountain. Pittsburgh would win another championship in 2016 and then repeated the feat in 2017.

Who will be the next star to assume Lemieux and Crosby’s mantle? Only time will tell.

T-7. The Edmonton Oilers: 5 Stanley Cups

If you live in a city like Toronto, Montreal, or New York, it can be easy to look down on Edmonton. From a hockey perspective, though, there was a time when the Alberta city was on top of the world.

Thanks to Wayne Gretzky — in fairness, he did have a strong supporting cast, including Glenn Anderson, Jari Kurri, Mark Messier, Kevin Lowe, Grant Fuhr, and Paul Coffey — the Oilers displaced the Islanders dynasty as the NHL’s dominant force. The club won the Stanley Cup in 1984, 1985, 1987, and 1988.

While many thought trading the Great One would end Edmonton’s success, that wasn’t the case. Behind a Conn Smyth-winning performance from Bill Ranford and 31 postseason points from both Messier and Craig Simpson, the Oilers took home the title in 1990.

T-5. The Chicago Black Hawks: 6 Stanley Cups

When we discussed the New York Rangers, there was talk of a curse preventing the club from winning a championship. The Chicago Black Hawks had their own story — the Curse of Muldoon — but that was tied to finishing in first place, rather than winning the postseason prize.

In the early days of the NHL, the club lifted two Stanley Cups (1934 and 1938). After that, a lengthy drought began, which was only broken in 1961. That championship gap, however, would seem brief compared to what would unfold.

After that title, the Black Hawks didn’t win another Stanley Cup until 2010, when Patrick Kane and Jonathan Toews (plus some others like Duncan Keith, Patrick Sharp, and Brent Seabrook) powered the club past the Philadelphia Flyers. Chicago would lift the big trophy again in 2013 and 2015.

Talk about making up for lost time.

T-5. The Boston Bruins: 6 Stanley Cups

In recent years, it’s seems like Boston is perpetually on top of the sports world. The Boston Bruins, however, didn’t play that large of a role in the success.

Half of the club’s Stanley Cup success came in the Original Six era. The Bruins first won the title in 1929 before repeating the feat in 1939 and 1941. Two more titles came to Beantown during Bobby Orr’s day (1970 and 1972) before the 2011 Bruins survived three game sevens en route to the title.

With all of that being said, though, the 2022-23 Bruins made NHL history with an eye-popping 63 wins and 133 points. That theoretically sets them up for a run at the title, even though postseason hockey is famously unpredictable.

3. The Detroit Red Wings: 11 Stanley Cups

In modern times, most Detroit sports teams have been rather disappointing. While that slump has affected the Red Wings, the club does have a rich postseason history.

The Red Wings won back-to-back Stanley Cups in 1936 and 1937 and added five more titles (1943, 1950, 1952, 1954, and 1955) before things tailed off. There were some lean years in the 1970s, but in the mid-1980s, the worm turned. The club went on an incredible postseason streak, reaching the playoffs in 30 of 32 years, including 25 straight seasons. As you might expect, that included a handful of championships.

The Stanley Cup returned to Detroit at long last in 1997, and the Red Wings won it again in 1998. The club would win the championship again in 2002 and add another banner to the rafters in 2008.

2. The Toronto Maple Leafs: 13 Stanley Cups

These days, the Toronto Maple Leafs are associated with postseason failure and a Stanley Cup drought. There was a time, though, when the club was piling up championships.

Toronto’s first title came in 1918 when they were still known as the Arenas. Another championship came to Ontario in 1922; this time, the club was known as the St. Patricks. Then, in 1932, the Toronto Maple Leafs, as we now know them, lifted the Stanley Cup.

The 1940s were especially dominant for Toronto, as the Leafs won the Cup in 1942, 1945, 1947, 1948, and 1949; another title came in 1951. The club lifted four more Stanley Cups in the 1960s (1962, 1963, 1964, and 1967) before things came to a grinding halt.

Yes, the Toronto Maple Leafs haven’t won a championship since 1967. Is it due to a curse? Simple bad luck? A variety of factors? No matter what you believe, it weighs heavily on the club and everyone affiliated with it.

Don’t believe us? Just consider this representation of “one man’s torture as a Leafs fan.”

That’s what decades of losing can do to a fan base.

1. The Montreal Canadiens: 23 Stanley Cups

Yvan Cournoyer (C) lifts the Stanley Cup in 1978.
The Montreal Canadiens celebrate winning one of their many Stanley Cup titles. | Bruce Bennett Studios via Getty Images Studios/Getty Images

Some franchises inspire a mixture of fear, awe, and hatred wrapped into one package. And, like the New York Yankees on the baseball diamond, the Montreal Canadiens have historically ruled the ice.

Over the years, the Habs have piled up an incredible 23 Stanley Cup titles. The first came in 1916, with the Canadiens also claiming the top spot in 1924, 1930, and 1931. In the 1940s, the famous “Punch Line” helped the club lift the 1944 and 1946 Cups.

While that would already be a rich history, the best was yet to come. Montreal won six championships in the 1950s, with five of those coming in one consecutive run (1953, then 1956, 1957, 1958, 1959, and 1960). Things didn’t really slow down after that, as the Canadiens added Stanley Cups to their trophy cabinet in 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, and 1979.

The streak of winning at least one title per decade continued in the 1980s (1986) and the 1990s (1993) before ultimately ending in the 2000s. And while it may provide some solace to Habs fans that the Canadiens were the last Canadian team to win the Stanley Cup, their current drought has been a bit too long for La Belle Province’s liking.


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