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Down Goes Brown: Revisiting my NHL Stanley Cup odds from 5 years ago. Howd I do?

Which NHL team has the best odds of winning the Stanley Cup in the next five years?

It’s a question I asked at Grantland in 2015, and again after joining The Athletic in 2018. That second column came exactly five years ago this month, meaning it’s a good time to look back and see just how wrong I was.

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I know I’ll be wrong, because one of the things you learn when you do an exercise like this is that predicting the future in today’s NHL is difficult, bordering on the impossible. There’s so much more randomness than we realize, and maybe even more than our fan brains want to process.

You also learn that when you’re trying to squeeze 32 teams into a five-year window, the odds for everyone get way smaller than you’d imagine, and that the margins get even smaller than that. You’ll see that in the rankings below.

Is it time for a brand new five-year window ranking? I’d say it is … soon. First, let’s look back at that 2018 list and see which teams I called reasonably well, and how many I whiffed on completely.

The Cup winners

Only four teams won the Cup in our five-year window because one repeated. So how’d I do? The results were mixed, and we may as well start with the worst call of the bunch.

St. Louis Blues

2018 ranking: 25th, with an 8 percent chance.

Yeah. On the one hand, I don’t think there’s any argument that the Blues were by far the most surprising team to win the Cup in our five-year window. On the other, they won the Cup the same year as this ranking, meaning they were just a few months away from a championship when I made the list, and said 24 teams were in better shape. I wasn’t the only one to miss it, but I definitely missed it.

Sentence that aged well: “It’s not all doom and gloom…”

Sentence that did not: “I thought the Blues were going to be reasonably good this year. I was wrong.” Look, anyone can be wrong, but it takes a special kind of dummy to be wrong about being wrong.

Preview for the next list: Probably a bit too high, since they already burned me once.

Vegas Golden Knights

2018 ranking: 14th, with a 14 percent chance.

They’d just been to the Stanley Cup Final, and the hockey world was trying to figure out if that was a fluke. In hindsight, this feels low, but remember that as an expansion team, they essentially had no prospect pipeline to speak of. It took them all five years, but they got there. Still had them in the top half, though.

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Sentence that aged well: “I’m a little concerned about Marc-Andre Fleury, who just turned 34 and isn’t going to play at least year’s level for the next five years.”

Preview for the next list: Reasonably high, based more on the short term.

Colorado Avalanche

2018 ranking: 7th, with a 22 percent chance.

Today, this feels like this should have been even higher, even though they were just one year removed from a 48-point season. But it’s worth remembering that their Cup win was the only time they made it out of the second round.

Sentence that aged well: “The elite talent is already there, and with some smart moves and a little luck, the rest of it could fall into place soon.”

Preview for the next list: Pretty high.

And that brings us to the two-time champs. Did I manage to see that coming? Well, about that…

Tampa Bay Lightning

2018 ranking: 1st, with a 40 percent chance.

I gave them 40 percent odds, and they won 40 percent of the Cups. You do the math, but I’m pretty sure that makes me a genius.

Sentence that aged well: “The Lightning are still my pick, even as the rest of the league closes in.”

Preview for the next list: They’ll be a tough one as their window slowly closes, and I think they may end up lower than their fans expect.

The finalists who didn’t win

The Lightning also lost a final, meaning we have four more teams to cover in this section.

Boston Bruins

2018 ranking: 8th, with a 21 percent chance.

They were still in the Zdeno Chara/Tuukka Rask era in 2018, although the clock was ticking loudly.

Sentence that aged well: “Even without much help on the way from the farm system, there are enough younger contributors on the roster that the Bruins won’t bottom out any time soon. They might even be able to contend for most of our five-year window.”

Preview for the next list: Another tough one, as they’re an aging team without a ton of prospect help on the way. Then again, we all seem to be in the habit of underestimating them.

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Dallas Stars

2018 ranking: 24th, with a 9 percent chance.

The Stars went to the final in those odd 2020 bubble playoffs, and hovered between good and great for pretty much the entire five-year window. Jake Oettinger and Jason Robertson had only just been drafted and hadn’t debuted yet, but yeah, this was too low.

Sentence that aged well: “Bubble teams can sometimes win Cups…” I meant the playoff bubble, because “bubble” didn’t have any other meanings back then, but this was weird to read five years later.

Sentence that did not: “… but if there’s a path to this team becoming something more, it’s hard to find.” Look harder, dummy.

Preview for the next list: They’ll be near the top.

Montreal Canadiens

2018 ranking: 22nd, with a 10 percent chance.

The Habs are a weird one, having one miracle run to the final in 2021 but being bad just about every other year. All told, I feel like this rating actually holds up.

Sentence that aged well: “It would only take one hot month from (Carey) Price to change some perspective here…” Could I interest you in two?

Preview for the next list: Teams in mid-rebuild are always tough, since it’s tempting to overrate their future prospects (a trap I’ve repeatedly fallen into both previous times).

Florida Panthers

2018 ranking: 21st, with a 10 percent chance.

They had a Presidents’ Trophy and a run to the final in the five-year window. They also had three seasons without a playoff series win, but this was too low.

Sentence that aged well: “The Panthers have a ton of good young players on the roster, and some year it’s all going to click.”

Sentence that did not: “… even with some decent reinforcements on the way, you wonder what the ceiling is.” Probably somewhere around 122 points.

Preview for the next list: Another tricky one, since their core will be aging out during the window, but they should at least land in the top half.

The contenders

Let’s look at a few other teams I had in the top half, and that are at least semi-defensible in hindsight.

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Toronto Maple Leafs

2018 ranking: 4th, with a 33 percent chance.

Remember, at this point, they’d lost in the first round twice, and it wasn’t A Thing yet. They’d also just ranked first in our future power rankings.

Sentence that aged well: “Maybe I’m overthinking it, or maybe this is my three decades of Leafs fan pessimism kicking in. But I’d like to see a team win at least one playoff round before I’m ready to put them in the top spot.” Yes. Yes, win one playoff round, indeed.

Sentence that did not: “If anything, the question might be why I don’t have them ranked even higher.” Good news: five years later, nobody is asking that question.

Preview for the next list: Somehow both too high and too low.

Mitch Marner, Auston Matthews and the Maple Leafs broke their first-round curse last season. (Bruce Bennett / Getty Images)

Washington Capitals

2018 ranking: 6th, with a 23 percent chance.

They’d won it all in 2018, and their high ranking was based almost entirely on their chances at getting another over the next couple of years. They won their division twice, but didn’t get out of the first round. Still, I don’t think ranking the defending champs high is all that hard to defend.

Sentence that aged well: “Can they hold it together long enough to win it all in 2022? Probably not.”

Sentence that did not: “Could they do it this year or next? Absolutely.”

Preview for the next list: Look away, Caps fans.

Edmonton Oilers

2018 ranking: 10th, with an 18 percent chance.

At the time, people pointed and laughed — the Oilers were a tire fire back then. But I was way more optimistic than most, and I think it holds up.

Sentence that aged well: “… a team built around (Connor) McDavid in his absolute prime, with Leon Draisaitl there, too. That team would absolutely have a good chance at a Cup, right?”

Preview for the next list: Probably pretty high, since they’re winning the Cup this year.

Calgary Flames

2018 ranking: 11th, with a 17 percent percent chance.

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Recency bias makes this look way too optimistic, but remember they had 107-point and 111-point seasons in our window. So, not a bad call for a team that was coming off a playoff miss.

Sentence that aged well: “Get them a goalie, and the rest of the pieces are there to at least have a puncher’s chance.” Jacob Markström looked like that guy for at least a while.

Sentence that did not: “… guys like Johnny Gaudreau and Sean Monahan are in their prime.” It’s weird to remember that there was a time when we thought Sean Monahan was a franchise-level star.

Preview for the next list: Not great.

San Jose Sharks

2018 ranking: 12th, with a 15 percent chance.

They’d just landed Erik Karlsson and still had Joe Thornton and Joe Pavelski. They were the most obvious “win-now” team on the list, and they’d go to the conference finals that year. It all fell apart after that, but honestly, I don’t hate what I wrote about them.

Sentence that aged well: “But at some point the clock is going to run out on this group, and there’s no obvious reinforcements on the way to replace them.”

Preview for the next list: In the running for dead last.

The bottom-dwellers

These were the teams I had little hope for.

Seattle Kraken

2018 ranking: 32nd, with a 3 percent chance.

We didn’t even know what they’d be called, and they’d only be in the league for two of our five years. The fact that I gave them any odds at all was a sign of how much I was hedging on the low end. And sure enough, they’ve already won a round.

Sentence that aged well: “I suspect that the other teams are going to smarten up in terms of how they handle expansion. They may even over-correct, hurting themselves in the process. But either way, Seattle is going to have a tougher time fleecing teams right out of the gate.” Pretty much exactly what happened.

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Preview for the next list: Higher than last time.

Chicago Blackhawks

2018 ranking: 30th, with a 6 percent chance.

They’d just missed the playoffs for the first time in a while, and the window seemed like it might be closed. In hindsight, it was.

Sentence that aged well: “And with a cap situation dominated by long-term contracts to aging stars who, for the most part, just aren’t ever going to be the players they once were, there’s little reason to think that things will get any better.” Pretty much.

Preview for the next list: They’ll be kind of fascinating. Connor Bedard will get this team into contention, but how quickly?

Ottawa Senators

2018 ranking: 29th, with a 7 percent chance.

I liked the young pieces that were already in place, but didn’t trust the larger organization to make it work. Honestly, I pretty much nailed it.

Sentence that aged well: “But if and when new ownership arrives, feel free to move the Senators up at least a few slots, and maybe more.”

Preview for the next list: Not high enough, according to the most optimistic fan base on the planet, but definitely a lot higher than 29th.

Detroit Red Wings

2018 ranking: 28th, with a 7 percent chance.

They were bad, and Steve Yzerman hadn’t even arrived yet, although we all knew he would.

Sentence that aged well: “I think the Wings are on the right track, but they’ll eat up a lot of our five-year window while they get there.” Bingo.

Preview for the next list: Oh good, another chance to debate how quickly the Yzerplan is proceeding.

Anaheim Ducks

2018 ranking: 23rd, with a 10 percent chance.

They’d just been swept in the first round. But they’d also won the Pacific every year from 2013 to 2017, so having them this low was just a little bit spicy.

Sentence that aged well: “The core is aging, the farm system isn’t great, the cap situation is messy, and while they have plenty of decent young talent on the roster and on the way, none of them project to be the kind of elite stars that Cup winners are built around.” This was pre-Trevor Zegras and Mason McTavish, so I’d say this checks out.

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Sentence that did not: “… they have one of the best goaltenders in the league.” That would be John Gibson, midway through what would turn out to be his last season getting Vezina Trophy votes during our window.

Preview for the next list: Another rebuild that won’t rank as high as their fans would hope.

Arizona Coyotes

2018 ranking: 20th, with an 11 percent chance.

They hadn’t made the playoffs since 2012, but whiz kid John Chayka was building something. We just weren’t sure what.

Sentence that aged well: “I’m not giving up on them yet, but the Coyotes have to get some traction at some point. And even if they do, the market and ownership situation limits their upside.”

Preview for the next list: Honestly, they might be about the same.

Middle-of-the-pack

I didn’t love these teams, but I didn’t hate them either. In other words: Pick a lane, coward.

Vancouver Canucks

2018 ranking: 13th, with a 15 percent chance.

They were coming out of a mini-rebuild, with Elias Pettersson and Brock Boeser in place and Quinn Hughes on the way.

Sentence that aged well: “… your confidence in Jim Benning and the ownership group to put the finishing touches on everything may vary.”

Preview for the next list: It will be interesting. They haven’t hit the peak that seemed reachable, but this year is inspiring some optimism again.

Carolina Hurricanes

2018 ranking: 15th, with a 14 percent chance.

Another one that seems off five years later, but in 2018 they hadn’t made the playoffs in nine years.

Sentence that aged well: “Maybe they eventually prove me wrong. It could happen as soon as this year.” Yep. They made the conference finals and have been contenders ever since.

Preview for the next list: Higher than 15th.

Philadelphia Flyers

2018 ranking: 16th, with a 13 percent chance.

They were in disarray at the time, and have already had to hit reset yet again. But they did have a very good 2019-20 season in our window, so this doesn’t hold up as badly as you might think.

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Sentence that aged well: “If anything, I’m betting that even diehard Flyers fans might think this ranking is too optimistic.” They did indeed.

Sentence that did not: “Chuck Fletcher has a mandate to get better right now.” Only because I wrote that like it was a good thing.

Preview for the next list: As overachieving rebuilders, they’ll be a very tough call.

New York Islanders

2018 ranking: 17th, with a 13 percent chance.

Five years has been a long time for this team. Back then, they had just lost John Tavares, and Lou Lamoriello had just arrived.

Sentence that aged well: “… aside from Mathew Barzal they don’t have anyone in the organization you’d describe as an elite talent in a league, where those are the guys that Cup winners are built around. So can Lou Lamoriello find a way to add those pieces? Maybe, although his recent track record makes you wonder.”

Preview for the next list: Oh no.

Minnesota Wild

2018 ranking: 18th, with a 12 percent chance.

It’s the Wild, so of course they were right in the middle.

Sentence that aged well: “… the prospect pipeline is poor, even as Kirill Kaprizov is intriguing.” I hear that guy turned out OK once he eventually showed up.

Preview for the next list: Right in the middle.

Pittsburgh Penguins

2018 ranking: 19th, with an 11 percent chance.

Remember, they’d just won the Cup in 2016 and 2017, so some fans thought I was way too low on them.

Sentence that aged well: “We know that the fall is coming. We just don’t know when.” You could argue that five years later, we still don’t.

Preview for the next list: Not great.

The Penguins’ Big Three of Sidney Crosby, Evgeni Malkin and Kris Letang may not have another shot at another Stanley Cup. (Bruce Bennett / Getty Images)

The whiffs

Finally, let’s close with a few teams where I probably just have to take the L.

Nashville Predators

2018 ranking: 2nd, with a 37 percent chance.

What?

OK, they were coming off a Presidents’ Trophy, and had been to the final in 2017, so this wasn’t completely absurd. But I was definitely way out over my skis here, as the Preds wouldn’t even win a round during the window.

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Sentence that aged well: “There isn’t a whole lot to choose from here between the Predators and Jets.” I mean, I was right, just not in the way I thought I’d be.

Sentence that did not: “With all of their stars other than Pekka Rinne under 30, the window isn’t in danger of slamming shut anytime soon…”

Preview for the next list: They won’t be second, although their ranking definitely might have a “2” in it.

Winnipeg Jets

2018 ranking: 3rd, with a 35 percent chance.

They were coming off a huge regular season followed by a trip to the conference finals, so optimism was high. In hindsight, they’d already peaked, as they didn’t win a game in the second round during our five years.

Sentence that did not age well: “I like Winnipeg’s odds of making at least a trip or two to the final.” The final what, weekend of the regular season?

Preview for the next list: Not third.

Buffalo Sabres

2018 ranking: 5th, with a 25 percent chance.

Let’s just call it what it was: This was me getting suckered by a hot start to the 2018-19 season, one that included a 10-game win streak. Don’t do your projections during the season, kids. Fun fact: I also had them way too high on the 2015 list.

Sentence that did not age well: “The Sabres spent years spinning their wheels, but now it seems like they’re finally on the move.”

Sentence that did: “Of course, when you hit the gas there’s always the possibility that you’ll speed up too fast, lose control and drive into a tree.”

Preview for the next list: Will he make the same dumb mistake for the third preview in a row? Tune in to find out.

Columbus Blue Jackets

2018 ranking: 9th, with a 20 percent chance.

This was the year that the Blue Jackets were facing an exodus of UFAs, including Sergei Bobrovsky and Artemi Panarin, and we didn’t know whether they’d sell or go all in.

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Sentence that did not age well: “Make no mistake, they’ve got the talent to win a Stanley Cup right now.” They did? (Checks their 2018-19 season page.) I mean, they had 98 points and did beat the Lightning, but seriously. Settle down.

Preview for the next list: I’m going to go ahead and say lower.

New York Rangers

2018 ranking: 26th, with an 8 percent chance.

This was a few months after The Letter that signaled a rebuild, but they were off to a solid start to the 2018-19 season, and I was worried they’d end up stuck in the middle. What I couldn’t have known is that there were two long-shot lottery wins to come in the next two years. What I might have known is that they’d sign Artemi Panarin, among other smart moves.

Sentence that aged well: “… the absolute worst thing that can happen in a rebuild is to win a few more games than expected and finish 18th instead of 28th.” They finished 26th, so apparently they agreed with me.

Preview for the next list: A ranking in the single digits for sure.

New Jersey Devils

2018 ranking: 27th, with an 8 percent chance.

The Devils ranked dead last on my 2015 list, and that held up. This one less so, although getting Jack Hughes certainly helped.

Sentence that aged well: “Still, there are some red flags, including … serious questions around whether $6-million goaltender Cory Schneider is still good enough to win with.” Remember Cory Schneider?

Sentence that did not: “But it’s hard to look at the Devils right now and not worry that they’re heading toward that mushy middle and not much further.”

Preview for the next list: A month ago, they’d have been in the running for the top spot. They might still be.

Los Angeles Kings

2018 ranking: 31st, with a 4 percent chance.

In my defense: The Kings are our final reminder that five years is a long time. In 2018, Rob Blake had only been there a year, the roster was old and they’d won one playoff game in four years. They had Ilya Kovalchuk!

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Sentence that aged well: “There’s talent coming through the system, but with an uninspiring NHL roster and a long-term cap situation clogged with big deals for declining veterans, there’s a ton of work to do in Los Angeles.” I mean, there was. And Blake got to work on doing it, and doing it very well.

Sentence that did not: “They might get there, but by the time they do, most of our five-year window should be gone.” Not quite, although they did miss the playoffs for three of the five years, and haven’t won a round. Still, they’re way ahead of where I thought they’d be.

Preview for the next list: I’m guessing I’ll probably nudge them up a spot or two.

All in all, I don’t think I did great, but I’ll give myself a passing grade because this is way harder than it looks.

Now it’s your turn. When the 2024 — 2028 list comes out, where do you think your team will rank?

(Top photo of Mark Stone after winning the 2023 Stanley Cup Final: Jeff Bottari / NHLI via Getty Images)

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Update: 2024-05-24