Last week, I wrote a piece about Canadian teams not winning the Stanley Cup. The drought is closing in on three decades, which is far longer than the math tells us should be possible. I came up with eight theories that could explain the streak, then picked them apart to see which ones held up.
The responses were interesting. Some of you agreed with the theories I posted, while others had theories of their own to share. Some Canadian fans admitted the whole thing bothers them, while others shrugged it off.
And some of you American hockey fans, like Jason here, decided to get cute:
Maybe if Canadian teams put together their payoff wins, they could reach the 16 win mark needed to lift the Stanley Cup https://t.co/AwlRjjtSpU
— Jason (@PREM1186) June 10, 2022
Well joke’s on you, Jason, because that sounds like a great idea, and we’re going to do a post about it.
Welcome to an alternate history where it’s 1993 and new commissioner Gary Bettman, feeling guilty over how he’s about to rig the entire league against Canada, throws us a bone: Canadian teams can pool their wins together, and whichever one gets win number 16 wins the Stanley Cup. It’s not about which Canadian team is the best or even which one goes further. Whoever gets that magic 16th win takes home the Cup.
Yes, this is dumb. Look, they made me write a grown-up post last week, you knew something like this was coming.
By allowing the whole country to pool their wins together to get to 16, we can kiss the drought goodbye. Also, we can remember some playoff runs. It’s mainly the second thing, to be honest, but I suppose the Stanley Cup is important too. Let’s harness the power of teamwork and bring home some championships, eh.
In our alternate history, Canadian fans in 1994 are very confused about why the new commissioner has put these weird rules in place. We’ve won the Cup eight of the last 10 years! Still, we’re Canadian, so we politely go along with it. And it pays off in a thrilling inaugural race to the Cup.
Four of the eight Canadian teams make the playoffs this year, with the Canucks, Flames, Leafs and Habs all punching a ticket. The Flames and Canucks play each other, and it’s a classic seven-game series that ends on Pavel Bure’s memorable winner. The Habs lose in seven to the Bruins, but the Maple Leafs take out the Blackhawks in six. Add it all up, and Canada already has 14 wins in the bank at the end of round one.
That sets up a furious race to 16 between Vancouver and Toronto. The Canucks get the 15th win in Game 1 against Stars, while the Leafs lose to San Jose. That means the Cup comes down to May 4, with both teams in action. Both teams win, but thanks to the magic of time zones, Toronto is celebrating win No. 16 while the Canucks are still on the ice in Dallas. East-coast bias strikes again, as Doug Gilmour’s goal and two assists bring the Cup back to Toronto.
No, I did not set up this whole dumb concept just so that the Maple Leafs would win a bunch of Stanley Cups. But for the record, if that ends up happening then I’m totally fine with it.
Winner: Toronto Maple Leafs
Fresh off the buzz of a Toronto championship, the country gears up for another race to 16. For the second straight year, four Canadian teams make the playoffs, with the Nordiques swapping in for the Habs. They get screwed by the refs in a six-game loss to the Rangers, while the Flames lose another seven-game heartbreaker to the Sharks and the Leafs are knocked out in seven by the Hawks. The Canucks come through again, though, beating the Blues in seven to emerge into the second round with 12 Canadian wins in the bank.
Then, uh, they get swept.
That’s it. Even with the ability to combine all their wins, the Canadian teams still can’t get to 16, and the Cup heads south. Huh. Let’s never speak of this again.
The good news: Five Canadian teams make the playoffs. The bad news: All of them lose, none lasting more than six games, so Canada stalls out at eight total wins. The worse news: The Nordiques have just moved to Colorado, and the Jets head to Arizona after this season, so we’re down to six Canadian teams.
For the second straight year, there’s no combination Cup winner. Wait, is this a drought? I was told there would be no droughts.
Only three Canadian teams make the playoffs, including the postseason debut of the Senators. They lose in seven to Buffalo on Derek Plante’s glove-snapping winner, while the Canadiens can only bank one win for the country before losing to the Devils. But the Oilers give us a thrilling upset win over the Stars before bowing out to the Avs in five in Round 2. Add it all up, and Canada has … nine wins. And no Cup. Again.
After a summer-long national conversation about how we still can’t win a Cup on easy mode, Canada is clearly not messing around for the 1998 postseason. Only the Senators, Habs and Oilers make the playoffs, but all three teams win their first-round series. The combined national total sits at 12 wins after one round with three teams still alive, and planning for the cross-country Cup parade begins. Then the three teams all get destroyed in Round 2, combining for just two more wins in the process, and the drought hits four seasons.
This idea sucks, man.
The Oilers and Senators make the playoffs, but both get swept in the first round. That leaves the Leafs to carry the entire load as the nation’s only hope, and I’m guessing I don’t have to tell you how that goes. Despite making the conference final, the Leafs can only bank nine wins, and with no help from the rest of the country, the drought is now five.
New millennium, new us. Except not really, as the same three teams make the playoffs, the Oilers and Senators bow out in the first round, and it’s down to the Leafs again. At least this time Edmonton and Ottawa chip in a few wins along the way, banking a combined three. But the Leafs get knocked out in Round 2, and the Cup-less drought hits six.
Note to self: Do the research first, then start writing, just in case your idea ends up being a dud.
Four Canadian teams make the playoffs, as the Leafs, Sens and Oilers are joined by the Canucks. But the Canucks don’t actually help, getting swept by Colorado, and the Leafs selfishly sweep the Senators without even letting them bank a courtesy win or two. Edmonton contributes two wins before bowing out to the Stars, and it’s once again all on Toronto. They lose their second-round matchup to the Devils in seven games, giving Canada a third-straight year of stalling out at nine combined wins.
In an emergency session of parliament, Prime Minister Gilmour threatens to withdraw the country’s teams from the NHL entirely if they don’t smarten up.
Finally, the dam bursts.
Four of our six teams make the playoffs, with Toronto, Ottawa, Montreal and Vancouver all volunteering for duty while Alberta sulks in the corner. In a show of unity, Toronto and Ottawa even agree not to play each other. And it pays off, as the Habs, Leafs and Sens all win their opening matchups. The only downside is Vancouver’s six-game loss to the Red Wings, after which Dan Cloutier is investigated for treason.
Still, that’s 14 wins on the board after one round, and with the Leafs and Senators facing each other in Round 2, the drought is guaranteed to end. The only question is which team will do it. The Sens claim win No. 15 in the opener in Toronto, giving Montreal a chance at the Cup the next night. But the Habs can’t get it done, losing to the Hurricanes, meaning Toronto and Ottawa meet on May 4 with win No. 16 on the line. Even better, the game goes into triple overtime, where a fitting national hero emerges to claim the Cup.
For the second time under our new rules, a Stanley Cup banner will hang in Toronto. I knew this was a good idea.
Winner: Toronto Maple Leafs
Devastated by their choke job in 2002, the Habs don’t even show up for the postseason party. But the Canucks and Oilers do, joining the Leafs and Senators for another strong national entry. The Leafs show admirable sportsmanship by refusing to hog all the championships, losing in the first round but banking three wins in the process. The Oilers add two more, and the Senators and Canucks win their matchups to head to Round 2 with the national total at 13.
The NHL decides to schedule the Canucks and Senators on the same night, and both teams win their series openers to boost the total to 15. Neither team can close the deal in Game 2, setting up an April 29 showdown with the Canucks in Minnesota and the Senators in Philadelphia. Ottawa has the Eastern Time Zone advantage, but they head to overtime while Vancouver gets to the second intermission in Minnesota with a lead. Ottawa needs to not just score, but do it early enough that the Canucks can’t close out the Wild in time. And they do, as Wade Redden sneaks one by Roman Cechmanek to capture the Cup. The Canucks hold on to get their win, but it’s too late. Too bad it wasn’t a Saturday night game against Toronto that started at 4:00, am I right Vancouver fans?
Winner: Ottawa Senators
With two straight Cups on the board, Canada is feeling it. They send five teams to the playoffs this year, with only the Oilers sitting out. The Leafs and Sens are playing each other, as are the Canucks and Flames, and both series go the full seven. So do the Habs against the Bruins, and I’ll save you the math: For the first time in the consolation Cup era, Canada will hit the magic number of 16 wins during the first round.
But who gets there first? The Leafs beat the Senators on April 16 to get the national total to 12, and the Canucks and Canadiens both win the next night. The Senators beat the Leafs on April 18 to get to 15, but both teams can only watch helplessly from their couches the next night. With a guaranteed win coming from either the Flames or Canucks, it comes down to whether the Canadians can go into Boston and beat both the Bruins and the clock. They do, winning in regulation while the Flames and Canucks go to overtime.
A fun note here is that in this version of reality, Alexei Kovalev’s fake injury in Game 4 was actually a brilliant strategic move that won the Cup for Montreal.
Winner: Montreal Canadiens
Canada has won three Cups in a row and Gary Bettman shuts the whole league down until he can figure out what’s going on.
Four more Canadian teams lead the charge, with the Senators and Oilers winning in the first round while the Flames and Canadiens chip in five wins in a losing cause. That puts the total at 13, and sets up an intriguing game of cat-and-mouse between the Senators and Oilers, who both lose the opening two games of their second-round series to try to force the other team into upping the number. The Oilers eventually bank win No. 14 on May 10, and with the Senators facing elimination the next night they have no choice but to post win No. 15. That gives the Oilers a chance at the Cup the next night, and they’re smart enough to grab the championship before something bad can happen to their goalie.
Winner: Edmonton Oilers
We’re down to the Senators, Canucks and Flames, but it’s enough as Ottawa and Vancouver escape the first round and the Flames chip in two wins before heading out. Vancouver loses to Anaheim in five, but the Senators advance again, and need just one win against the Sabres in Round 3 to capture the Cup. They get it in Game 1 in Buffalo.
Winner: Ottawa Senators
Realizing that America hasn’t won a Cup since 2001 and worried that the NHL is going to change the rules back to something that makes sense, Canada executes a strategic retreat. We send only three teams to the playoffs, with Ottawa and Calgary making early exits and the Canadiens going meekly in Round 2. With only eight wins, Canada ties its all-time low from 1996. See, America, there’s no need to change anything.
Vancouver swaps in for Ottawa, but otherwise, 2009 is a rerun. Three Canadian teams make the playoffs, only one makes Round 2, and when the Hawks finish off the Canucks in six games, it leaves Canada with just a combined total of eight playoff wins for the second straight year.
Wait, can we combine 2008 with 2009 to get to 16 and claim another Cup? Of course not, that premise would feel implausible.
Having sufficiently placated the foolish Americans, Canada gears back up for another Cup run by sending Ottawa, Montreal and Vancouver to the postseason. The Sens chip in two wins on their way out, while the Canucks and Canadiens both win their Round 1 matchup to bring the national total to 10. After some strategic give-and-take early, both teams are facing elimination and in must-win mode when Vancouver banks win No. 14 in Chicago on May 9. The Canadiens return the favor the next night against Pittsburgh, handing the Canucks a shot at a championship. They can’t bring it home, losing to the Hawks on home ice, and the Habs finish the job the next night in a Game 7 win in Pittsburgh. Jaroslav Halak is immediately granted Canadian citizenship.
Winner: Montreal Canadiens
The odds seem slim as Montreal and Vancouver are the only two Canadian teams to make the playoffs and the Habs go out in seven to Boston. But the Canucks go on a run, carrying almost the entire load and entering the Final against the Bruins with 15 national wins on the board. A scoreless nail-biter in the opener comes down to a Raffi Torres goal with seconds left, which brings the Stanley Cup back to Vancouver.
Nobody remembers anything else that happens in this series.
Winner: Vancouver Canucks
The season starts off well for Canada, as the Winnipeg Jets return after a 15-year absence. They miss the playoffs, though, as do four other Canadian teams. That leaves it up to the Canucks and Senators, and this time neither can even get out of the first round. At four combined wins, it’s Canada’s lowest total of the consolation era. Everyone agrees that this is Winnipeg’s fault.
Four teams make the playoffs, including the return of the Maple Leafs after almost a decade off, which I’m sure will go great for them. But only Ottawa wins in the first round, and the other teams can only supply them with four wins’ worth of headwind. It’s not enough, as the Senators go out quickly to the Penguins and the national tally stalls out at nine wins.
Montreal is the only Canadian team to make the playoffs, meaning they have to win 16 playoff games all by themselves, which I think we can all agree is mathematically impossible. They do make a run, winning two rounds before Bettman passes a new rule that makes dropkicking goaltenders legal. The Habs’ heroic run ends at 10 wins, and Canada has once again gone three straight years without a Cup.
One year after hanging Montreal out to dry, it’s almost all hands on deck, as five Canadian teams make the playoffs. The Jets are swept, but the other four teams make a strategic decision to go head-to-head to maximize win potential. It works, as the Habs beat the Sens in six and the Flames do the same to the Canucks, putting the country at 12 wins through Round 1 with two teams still standing. The Flames add another win and the Habs get two more, leaving the country one win away from ending their drought. The Flames get the first shot, and are an overtime goal away against Anaheim when despicable traitor Corey Perry cheats to eliminate them.
The Canadiens can’t take advantage against Tampa, and for the first time in consolation Cup history, Canada stalls out at an agonizing 15 wins. Man, that’s painful. It would almost be better to not have any playoff teams at all.
A year after no-showing the postseason entirely, Canada sends five teams. The Leafs, Canadiens and Flames all lose in Round 1, chipping in four wins on the way out, as attention turns to the Senators and Oilers. With 12 wins in the bank, it’s a second-round race between Connor McDavid’s Oilers and Erik Karlsson’s Senators, and both teams go all-out early on and trade wins. That gives the first chance to Ottawa, and on April 29 they host the Rangers with the Cup in the building. In perhaps the greatest championship-winning performance in NHL history, Jean-Gabriel Pageau puts the country on his back and ends a five-year drought.
Realizing that this dramatic performance can never be topped, the Senators immediately announce their retirement from playoff competition.
Winner: Ottawa Senators
Toronto and Winnipeg are the only two teams to qualify for the postseason, and after the Leafs bank their customary three-win exit, it’s all on the Jets. They make a run, lasting until the third round, but are eliminated by the Golden Knights four wins short of a Cup.
The Flames, Jets and Leafs all qualify, but Calgary and Winnipeg make early exits. That leaves it all up to the Maple Leafs in a first-round Game 7, and that goes exactly as well as you’d think it would.
The weird pandemic playoffs send 24 teams into the bubble, including all the Canadian teams except Ottawa. The Jets, Leafs and Oilers are all knocked out before the formal playoffs begin, though, and the Flames and Canadiens are both eliminated in the first real round. They donate four wins to the cause, but that’s not enough for the Canucks, who stall out at 11 national wins when the Golden Knights take them out.
With three straight Cupless seasons, desperate times call for desperate measures: The all-Canadian division, which guarantees the country four playoff teams and at least 12 wins. But two of the division’s three series are sweeps, meaning the Canadiens emerge into the third round with a national total of 15 wins, one short of the Cup. Facing a Golden Knights team that everyone thinks will sweep them, the Habs lose the opener, and disaster looms. That’s when good Canadian boy Marc-Andre Fleury steps up, “accidentally” allowing Montreal to build a 3-0 lead in Game 2. It holds, barely, and the Canadiens have another championship.
Immediately after the game, the Habs sign Dominique Ducharme and Marc Bergevin to record-breaking extensions, ushering in a brave new era of Montreal dominance.
Winner: Montreal Canadiens
And that brings us to this year, which featured three Canadian teams. After Toronto’s trademark three-win donation and opening-round wins by the Flames and Oilers, the country sits at 11 wins heading into the Battle of Alberta.
The entire country casts its eyes ahead to Game 5, which is guaranteed to be for the Cup. It ends up being a classic, one that features nine goals — including one from the opposite blue line — on the way to a fitting ending from the greatest player in the world.
Winner: Edmonton Oilers
Adding it all up…
After running the numbers and fighting off a sinking feeling that I have wasted my life, the results are in. Despite a generous and, let’s be honest, completely ridiculous advantage, Canada still managed to win just 11 Stanley Cups in 28 seasons. We had droughts of seven and five years, as well as a streak of eight whiffs in nine seasons. That seems bad. Like, I’m honestly a little depressed right now. Wait, did Jason know how this was going to turn out, and I walked right into his trap? The internet was a mistake.
But we did add 11 championships to our national total, so let’s focus on the positive. The Canadiens and Senators led the way with three each, while both the Oilers and Maple Leafs miraculously managed two. The Canucks had one, meaning that even in our ridiculous alternate reality, the Flames and Jets still came up empty. At least Winnipeg didn’t have a team for half of our history. Calgary, I’ve got no idea what’s up with you guys, but we’ll get Prime Minister Gilmour on the case and let you know.
(Photo: Adrian Wyld / The Canadian Press via AP)