Which Canadian Team Has the Best Chance to Win the Stanley Cup in 2023?

A brand new NHL season has arrived, and it's hit with the same question fans in Canada have asked for so long: is this finally the year? We all know about Canada's cup drought, which will reach an even three decades if none of the seven teams capture Lord Stanley's Cup this season. When the Montréal Canadiens defeated the Los Angeles Kings in the 1993 Stanley Cup Final, it was not only the franchise's 24th Cup, it was also the last Cup won by a Canadian team. When the drought began, there were eight teams in Canada: the Vancouver Canucks, the Edmonton Oilers, the Calgary Flames, the Winnipeg Jets, the Toronto Maple Leafs, the Ottawa Senators, the Quebec Nordiques, and the Montréal Canadiens.

1995-96 saw the Nordiques move to Denver and become the Colorado Avalanche (and win the Stanley Cup that same year), while the following year saw the Winnipeg Jets move to the desert and become the Phoenix (now Arizona) Coyotes. The remaining six teams continued on, but after the end of the 2010-11 season, the Atlanta Thrashers moved to Winnipeg and became Jets 2.0. In the years that passed, none of the NHL's Canadian teams won the Stanley Cup, but we have seen Canada represented in the Cup Final on a few occasions. This past season saw a Canadian team in the NHL's Final Four for the fourth time in the last six seasons, but even so, no success.

So will Canada do it this year? Here's a look at each of the seven teams, and their chances to capture the Cup:

Montréal Canadiens

While the Canadiens do have the most Stanley Cups with 24, they have not won since 1993. The Habs have reached the playoffs 18 times since their last Cup, but have only reached the Final Four three times out of those 18 appearances. However, they are the last Canadian team to reach the Final, doing so during that memorable Cinderella run in 2021. Sadly, the Canadiens had nothing for an encore, as the 2021-2022 season was a disaster for them. The team finished dead last in the entire league, but even then, there was some positivity, as the hiring of Martin St. Louis during that season has led to a resurgence in a number of the team's players, especially Cole Caufield.

Caufield was considered a Calder favorite entering last season, but he regressed big time, leading to a demotion to the minors. St. Louis' hiring led to Caufield scoring goals left and right at the tail end, and it has fans believing that the Habs could be on the rise. As for a Stanley Cup, though, their chances aren't that strong. The playoffs are still a bit of a stretch as well, but if they get a few more pieces, they could be a playoff team in 2023-24.

Ottawa Senators

I still remember the Senators magical playoff run back in 2017. It was just amazing; they ousted the Boston Bruins and the New York Rangers in the first two rounds, and in the Eastern Conference Final, they went toe-to-toe with the then-defending Stanley Cup Champion Pittsburgh Penguins. The Sens took the Pens to double overtime of Game Seven. They had a pretty good chance to deliver a huge upset, but Chris Kunitz decided to end Ottawa's season with one hard shot. Even so, the Sens came within a hair of their second-ever appearance in the Cup Final, and it looked like there were good things ahead.

Then the Matt Duchene trade happened.

Funny how one trade managed to cause such a paradigm shift. The Sens were one of three teams who were involved in the November 5, 2017 deal, with the others being the Colorado Avalanche and Nashville Predators. As a result of the trade, the Predators (who were coming off reaching the Final) continued to remain a perennial playoff team, and the Avalanche were resurrected to playoff prominence and an eventual Stanley Cup in 2022. But the Sens? Death. The trade killed them. Even worse, a 1st round draft pick was sent to the Avs, and because the Sens actually had the league's worst record in 2018-19, the Avs (a playoff team who nearly reached the Final Four) were in the lottery (the Avs ended up with the #4 pick, which became Bowen Byram). The Senators continued to be terrible in the years that passed, but they would have big deals left and right during the off season.

Players such as Claude Giroux, Alex DeBrincat, and Cam Talbot became Senators during the offseason, while Brady Tkachuk continues to serve as the team's top star. Many have the Sens reaching the playoffs this year, but as for winning the whole thing? Not likely, but they could make a run if things go right.

Winnipeg Jets

Neither iteration of the Winnipeg Jets has reached the Stanley Cup Final. In fact, the original Jets never even reached the conference finals in their entire 17 season tenure in the NHL (they won the Avco Cup three times when they played in the WHA from 1972-79), and only reached the Final Four once since moving to Arizona (2011-12). As for the current Jets team, they hadn't won a playoff game in their first two appearances, but their third would finally see them win one--and then add eight more. Since that run to the Western Conference Final in 2018, the Jets have had problems advancing in the playoffs, only winning one series ever since (the 2021 North Division Semifinal vs the Oilers).

The Jets are a loaded team, with players such as Nikolaj Ehlers, Mark Schiefele, Blake Wheeler, Josh Morrissey, and most importantly, Kyle Connor. They also have an amazing goalie in Connor Hellebuyck, who won the Vezina Trophy in 2020. I think the Jets are a playoff team in 2022-23, but as for the Stanley Cup, they have no chance. The Jets are in a brutal and cutthroat Central Division, and it will be hard to get past teams like the Avalanche and the St. Louis Blues.

Vancouver Canucks

After the 2021-22 season started with no get-up-and-go, the Canucks cleaned house. Travis Green was gone. Jim Benning was gone. Enter Jim Rutherford, who built up the Carolina Hurricanes and the Pittsburgh Penguins, and enter Bruce Boudreau, an instant coaching legend. The result was a resurgence that saw the team and its players flourish, but it was only good enough to be the last Canadian team to be eliminated from playoff contention last season. Even so, there is optimism when it comes to the Canucks.

Canada's Cup drought started with the Canucks. The season after the Canadiens won the Stanley Cup, the Canucks reached the Stanley Cup Final, but were defeated by the New York Rangers. They would return to the Final again in 2011 after a very dominant season, but they fell short again, this time against the Boston Bruins. The Canucks are the only Canadian franchise to reach the Final twice during the ongoing Canadian Cup drought, but since their 2011 appearance, it's been nothing but disappointment and disaster. The run in the 2020 bubble was their best since 2011, but it was followed by finishing dead last in the all-Canadian North Division in 2021. This is Vancouver's first full season with Boudreau as coach, and I see them being a playoff team, though I cannot see them getting past the Oilers.

Toronto Maple Leafs

Oh man. I really, really, really want to say that the Maple Leafs have the best chance out of the NHL's Canadian teams...but I can't. I can't, in all honestly and fairness, say that the Leafs have the best chance to end Canada's Cup drought, and it's because of their offseason. I seriously don't know what the Leafs are trying to pull with the moves they've made, but I know this, it's not an improvement. As if losing Zach Hyman during the last offseason wasn't bad enough, the Leafs' 2022 offseason decided to top that by losing not only Jack Campbell, but Ilya Mikheyev as well, while also being fleeced by their provincial rivals into taking Matt Murray. Yikes.

The Leafs keep losing key players, and we all know why. It's because a vast majority of their cap is going to four players: John Tavares, William Nylander, Mitch Marner, and of course, Auston Matthews. A good group of players. But that can't be all you have. The Leafs have the worst negatives hanging over their heads. No Cups (or Cup Final appearances) since 1967. They haven't reached the Final Four since 2002, and they now have the longest playoff series drought in NHL--having not advanced since 2004. The Leafs should be a playoff team again this year, but I am very unsure of their chances of winning the Cup this year. I could be wrong.

Calgary Flames

The Calgary Flames had a very good 2021-22 campaign; finishing first in the Pacific Division and surviving a seven-game thriller over the Dallas Stars. However, when it came to Round 2, the Edmonton Oilers ended up being way too much for them. Even worse for the Flames, they ended up losing two-thirds of their top line, as Johnny Gaudreau left for Columbus, and Matthew Tkachuk went to Florida in a deal that sent Mackenzie Weegar and Jonathan Huberdeau to the Flames, who clearly got fleeced by the Panthers. However, they did make up for it by signing Nazem Kadri (who is coming off winning the Stanley Cup with the Avalanche) to a big deal.

The Kadri signing prevents Calgary from actually missing the playoffs this season, but do they have a chance at the Cup? Their only Cup in franchise history came in 1989, and the last time they reached the Final was in 2004, the magical run that saw them fall one win short. They have not reached the Final Four since then, and with the team they have now, while it is a playoff team, they won't go too far.

Edmonton Oilers

Last, but not least, we have the Edmonton Oilers. After losing the Qualifying Round in 2020 to the Chicago Blackhawks (on Edmonton's own ice), and after being swept in the opening round by the Winnipeg Jets, the Oilers loaded up and ended up with Evander Kane right on their laps. The result saw the Oilers go all the way to the Western Conference Final, which was their first Final Four trip since their Cup Final run in 2006. The Oilers ended up swept by the Avalanche, but in hockey, the ultimate response to being punched in the mouth: loading up.

In this case, the Oilers snagged Jack Campbell from the Toronto Maple Leafs; a move that was done to create consistency in net, which they did not have with Mike Smith. I'm going to be serious; the Oilers are going to scare teams this year. They have actual depth. It's not just McDavid and Draisaitl carrying the load. Out of all seven Canadian teams, the Oilers truly have the best chance to win the Cup. However, there's just one thing they have to do to win their sixth Stanley Cup: avoid the Avalanche.

So that's a look at all seven Canadian teams and each of their chances to win the Stanley Cup in 2023. Will one of them break through and do it, or will the drought actually reach 30 years? This season will tell the tale.