How Bad Is It? Ranking the NHL's Original Six by Fan Misery

The NHL’s original six franchises are not exactly making Stanley Cup Championship headlines these days. 

Some have endured years without playoff hockey. Others have suffered heartbreaking postseason collapses. And in Toronto, an entire generation has grown up without seeing the Maple Leafs lift the Stanley Cup.

It’s not all bad; the Montreal Canadiens seem ascendant, and the Boston Bruins are postseason staples, but for the most part, it’s been a decade to forget for the Original Six.

It got us thinking about which fanbase is suffering the most. The best way to settle it is ranking the NHL’s Original Six franchises by how much misery their fans have endured.

How Is Fan Misery Measured?

There is no scientific method to figuring out the most miserable fanbase. Instead of simply ranking teams by worst win percentages and negative social media comments, we took several factors into consideration, including:

• Years since the last Stanley Cup
• Length of major championship droughts
• Recent playoff failures
• Painful eliminations or collapses

No. 6 to No. 1: The Original Six Misery Rankings

6. Blackhawks

Chicago has been the most successful Original Six franchise in the modern era, winning three Stanley Cups between 2010 and 2015. Fans haven't had much to cheer about in the 11 years since, as the Blackhawks missed the postseason eight times and suffered a first-round exit the other three times. For those hoping that the 2026-27 NHL season is finally going to be when the franchise turns things around, current sports betting odds have Chicago priced at +500 to make the playoffs. For those seeking positive news that might help ease the pain, Anton Frondell and Roman Kantserov are considered to be among the NHL’s top prospects for the 2026-27 season. 

5. Bruins 

Boston has been one of the better Original Six teams over the past decade, making the Stanley Cup Playoffs nine times. The 2019 season was highlighted by a Stanley Cup Final appearance (losing to Saint Louis). The most recent of the six championship seasons came in 2011 when the Bruins defeated the Vancouver Canucks in seven games. It was the franchise’s first since 1972.

Boston is among the early Eastern Conference leaders, but FanDuel has the Bruins at -310 to miss the playoffs and +230 to make it. Waiting 15 years for a championship is minimal compared to Original Six fanbases that have been waiting since before any of the current NHL players were born. Even Buffalo Sabres fans have it tougher, as the franchise has won zero championships in 56 seasons.

4. Canadiens 

One could make a strong argument that Montreal fans have no excuse for being miserable, given that the Canadiens have won an NHL-record 24 Stanley Cups.

Sure, they’ve been waiting 33 years since the last one, but there are 10 NHL franchises still chasing the first one. The Habs are sitting in the fourth spot because the franchise has qualified for the postseason just four times since 2017. The most recent of those appearances came during the 2025-26 season when Montreal lost the conference finals to the eventual champion Carolina Hurricanes. The Canadiens have the best Stanley Cup odds (+2200) out of the Original Six members. 

3. Red Wings

Detroit is known as Hockeytown, but the Red Wings, previously known as the Cougars and Falcons, are going through one of those dreaded periods centered around 10 straight seasons without a postseason appearance.

Since winning the 2008 Stanley Cup and making the championship round the following season, this franchise has not made it out of the second round. The upside is that the 11 Stanley Cups rank third behind the Canadiens and Maple Leafs (13). When Red Wings fans are feeling down, they can look at the accomplishments of the other Original Six franchises and say “four championships since 1997 doesn’t seem so bad.” However, current fans' misery levels are not expected to improve this season due to the fact that Detroit’s odds of missing the playoffs are -350. 

2. Rangers 

Is there something in the New York air? The Rangers' last Stanley Cup win came in 1994, but the 32-year wait isn’t just a hockey problem. Knicks fans waited 53 years to see their basketball team finally win another championship.

The Yankees, once known as baseball’s “Evil Empire,”  last won the World Series in 2009. The Rangers’ most successful run came between 1928 and 1940 when they were crowned league champion three times. The last decade has produced a mixed bag of results as the franchise missed the playoffs five times and made two trips to the conference finals. Now that the Knicks have won, could the Rangers finally be next? If we’re basing the answer on FanDuel Sportsbook futures, expect another miserable June as New York is a very long shot to win the Stanley Cup.

1. Maple Leafs 

Hey Maple Leafs fans, we can’t imagine the level of heartache and pain you deal with every Spring. Even though the franchise ranks second all-time with 13 championships, you have to go all the way back to May 2, 1967, to find when the most recent one happened. It means Toronto is still seeking its first title since the league expanded beyond six teams.

While making the postseason eight out of the last 10 seasons is a positive, the Leafs won only two playoff series during that time. Miserable Leafs fans might have the bar set so low at this point that when the franchise finally does make it back to the conference final (last appearance came in 2002), it might feel like a championship season. The upside is Toronto used the No. 1 overall pick to draft Gavin McKenna, who comes with extremely high expectations for this season.

Does Winning in the Past Make Losing Hurt More?

When talking about hockey’s most famous and historically successful franchises, fans can look at all of the championship banners hanging from the rafters. Once they pull out their cell phones and zoom in on the year, the pain is hard to avoid.

Maple Leafs fans have been waiting a lifetime for that next Stanley Cup championship moment. When a new season rolls around, there is hope that it will be the one that their favorite franchise finally turns the corner. By the time June arrives, the misery of another disappointing season takes over.