NHL

Which teams have the most invested in winning in the 2022-23 season?

Contention windows in the NHL are fickle and unpredictable. Teams launch themselves head-first into miserable rebuilds and emerge excited about playoff runs that never materialize; perennial contenders fall off the map and into the lottery with little to no warning; star players break out and fall apart; payrolls become suffocated by former franchise players' huge cap hits.

Given all this uncertainty combined with the limited tenure of general manager jobs, competitive teams face a ton of pressure to sacrifice the future for the present, maximizing what opportunities they have to win now. This in turn allows organizations lacking in talent to be more patient, upwardly redistributing their top players to playoff teams and accumulating assets.

A few weeks back, Danny Heifetz and Riley McAtee of The Ringer published a piece in which they used NFL teams' draft capital and spending to rank each team based on how "all-in" they are on the 2022 NFL season. Differences between the two sports make a 1-to-1 adaptation of this system impossible (for example, the way almost every team is up against the salary cap), but inspired by their approach I'm going to rank all 32 teams by how "win-now" they are going into the 2022-23 NHL season.

Despite the common perception that "tanking" is a pervasive issue and legions of teams are throwing seasons for high picks, the NHL is a highly competitive league. Very few teams -- arguably only three -- are intentionally trying to lose this season despite the presence of a franchise player in the draft in Connor Bedard. The rest are at least trying to win hockey games, although their competence at doing so remains very much to be seen.

There are five factors I considered that contribute to how all-in a team is for the coming season:

  • Draft Capital: This refers to how many future assets the franchise has accrued in the form of draft picks in the coming years. First-round picks are the most valuable, with second- and third-round picks valued in proportion to their expected value relative to the firsts. Considerations also include the expected placement of those picks in each round. The higher score, the more draft capital.
  • Prospect Pool: This refers to how many future assets the franchise has accrued in the form of young prospects who have yet to make an impact in the NHL. This will be informed by the EP Rinkside prospect pool rankings. The higher score, the better prospect pool.
  • Age of Core: One of the biggest factors determining how all-in a team is is the age of their core players. The higher the score, the older their core is.
  • Cap Constraints: A looming salary cap crunch or catastrophe can abruptly end a team’s contention window -- just ask the San Jose Sharks. The higher the score, the more restrictive their cap outlook.
  • Competitiveness: How competitive the team projects to be in the 2022-23 NHL season. The higher the score, the better chance they have of winning this season.

Pure Rebuilders

32. Arizona Coyotes

Draft Capital: 9/10

Prospect Pool: 8/10

Age of Core: 3/10

Cap Constraints: 2/10

Competitiveness: 1/10

What exactly are the Arizona Coyotes doing? Whatever it is, it has very little to do with trying to win hockey games at any point in the near future. They lack any other teams’ first-round picks (although that will likely change whenever they finally get around to moving Jakob Chychrun), but all indications would suggest that their own top picks will be excellent ones. It’s a good thing, because a core of Clayton Keller and Nick Schmaltz isn’t going to cut it. Logan Cooley and Dylan Guenther are the beginning of something good, but beginning is the operative word.

31. Chicago Blackhawks

Draft Capital: 9/10

Prospect Pool: 6/10

Age of Core: 5/10

Cap Constraints: 3/10

Competitiveness: 1/10

It’s easy to remember a time when the Chicago Blackhawks believed they were entering a window of renewed contention, led by a new, young core of Seth JonesAlex DeBrincat, and Kirby Dach. It’s easy because it was a year ago. A catastrophically disappointing season and a total front office overhaul has seen two of those players traded and a total organizational reset. 

The Blackhawks have amassed a well-stocked war chest of draft picks, headlined by basically half of Tampa Bay’s selections in the next three years. With rentals Patrick Kane and Jonathan Toews seemingly destined for greener pastures before the trade deadline, they should have even more by the time the 2023 NHL Draft rolls around. With the team in tank mode and a set of elite pieces on the board this year, their first-round pick could be a franchise-altering one. Their delayed rebuild and the Jones trade have robbed their pool of talent, but Kevin Korchinski looks to be a difference-maker.

The cap board is pretty much clear aside from Jones’ whopping deal, so the Hawks should have plenty of flexibility to build for the future. Nobody has the smallest expectation of them winning this season.

30. Montréal Canadiens

Draft Capital: 9/10

Prospect Pool: 8/10

Age of Core: 4/10

Cap Constraints: 7/10

Competitiveness: 2/10

Two years ago, a Cup finalist. Now, a projected Connor Bedard finalist. Things went off the rails fast in Montréal, and the awkward position of their rebuild is a testament to it. The Habs remain stuffed with middle-to-long-term deals signed to maximize a contention window that never came, and their core of Nick SuzukiCole Caufield, and Juraj Slafkovský will likely be sharing the ice with a lot of those players for a few years to come. Kaiden Guhle and Owen Beck help flesh out a good prospect pool, but barring a shocking turn of events the Habs have no intention of competing in the short term.

29. Buffalo Sabres

Draft Capital: 7/10

Prospect Pool: 10/10

Age of Core: 3/10

Cap Constraints: 3/10

Competitiveness: 3/10

Back in 2015, the Sabres doomed their rebuild by getting over-excited and trying to compete right away. With the faulty Rasmus Ristolainen cast as the No. 1 defenceman, Buffalo filled out their lineup with pricey and lengthy free agent deals to aging veterans that bogged down a young developing team and led ultimately to the need for a do-over.

The do-over is doing pretty well, all things considered. The Sabres have one of the top prospect pools in hockey, headlined by Owen PowerJack Quinn, and Matthew Savoie, almost all of their own picks and a couple others, and plenty of cap space to work with moving forward. It’s too early to tout a success here, as we learned the last time, but they have not yet made the kinds of errors that doomed the Jack Eichel era. While some fans might be a little over-excited about the team’s outlook this season, the front office appears to have embraced a building strategy emphasizing flexibility and patience.

28. Anaheim Ducks

Draft Capital: 8/10

Prospect Pool: 9/10

Age of Core: 3/10

Cap Constraints: 6/10

Competitiveness: 3/10

The Ducks finally accepted that a rebuild was necessary last season, moving Hampus LindholmJosh Manson, and Rickard Rakell a few years too late to maximize their value but nonetheless helping build out their asset base. Trevor ZegrasMason McTavish, and Jamie Drysdale are the future in Anaheim, and while the front office might have gone a bit overboard in free agency to keep the team from getting laughed off the ice every night, a playoff spot would be a surprise.

27. Detroit Red Wings

Draft Capital: 7/10

Prospect Pool: 9/10

Age of Core: 5/10

Cap Constraints: 6/10

Competitiveness: 5/10

The draft lottery has thwarted Detroit’s loftiest expectations of their rebuild, but with strong pieces like Moritz SeiderLucas Raymond, and Simon Edvinsson, it’s not like they left their darkest years empty-handed. That said, the lack of a high-end centre of the future is troubling, and with the 26-year-old Dylan Larkin and 27-year-old Tyler Bertuzzi staring down unrestricted free agency, the team’s struggles to find high-end forward talent in the draft might sabotage the team’s plans to contend. A slew of big-name free agent adds this summer announced that the Wings are ready to at least stop losing, and while I sincerely doubt they see this season as their best shot at winning, the path forward is murkier than one might prefer.

26. Ottawa Senators

Draft Capital: 6/10

Prospect Pool: 7/10

Age of Core: 2/10

Cap Constraints: 7/10

Competitiveness: 5/10

The ultimate success of the Senators rebuild has been a source of heated discussion in recent years, and its culmination in a series of aggressive roster moves and expensive long-term extensions has only upped the pressure. Tim StützleAlex DeBrincatBrady TkachukJosh NorrisDrake BathersonThomas Chabot, and Jake Sanderson are the future of the Ottawa Senators, and they'll either win with that group or not. That’s not to say that this team is a finished product or in any real hurry; the big contracts have either already started or start next season, so we’re mostly past the point of capitalizing on entry-level deals. Unlike the Los Angeles Kings or New York Rangers, the Senators do not have an expensive veteran core in parallel with the kids, which gives the Sens more time to be patient.

25. Los Angeles Kings

Draft Capital: 6/10

Prospect Pool: 5/10

Age of Core: 6/10

Cap Constraints: 8/10

Competitiveness: 6/10

The Kings aren’t the only team that jammed the accelerator after wrapping up a multi-year rebuild, but they have plenty of questions surrounding what the team will really look like moving forward. Is the franchise’s real core the group of Quinton ByfieldBrandt ClarkeArthur Kaliyev, and Alex Tucotte; is it Drew Doughty and Anze Kopitar; is it Phillip DanaultAdrian KempeAlex Iafallo, and Kevin Fiala? The organization’s apparent struggles to develop prospects into high-end NHL pieces in recent years have made it tough to say exactly when the team is supposed to start really winning. Like the Rangers, ideally this group will find a sweet spot where the youngsters turn into stars while the vets can still contribute, but the clock might be ticking on that plan.

24. San Jose Sharks

Draft Capital: 6/10

Prospect Pool: 7/10

Age of Core: 8/10

Cap Constraints: 9/10

Competitiveness: 4/10

The Sharks faced a key inflection point in their franchise’s history last season, with star centre Tomáš Hertl’s contract set to expire. A trade followed up by moving 25-year-old Timo Meier would have set the team up with some high-end assets and announced that the floundering franchise is ready to rebuild. Not yet. An eight-year extension with a no-move clause suggests that it’s mostly status quo in San Jose. Moving Brent Burns was a step in the right direction, but this team does not have the prospect base or flexibility to fully commit to a tear-down. The team is not good enough to be all-in (Scott Harrington is projected as a top-pairing defenceman), but the direction of the franchise is unclear.

23. Philadelphia Flyers

Draft Capital: 7/10

Prospect Pool: 5/10

Age of Core: 7/10

Cap Constraints: 8/10

Competitiveness: 3/10

Ask anyone who follows hockey -- especially a Flyers fan -- and they will tell you that Philadelphia’s outlook is pretty bleak at present. The team seems attached to a core that ranges between 25 and 31, prime-aged and set to go downhill from here but composed entirely of players who are at best good and at worst significantly overpaid. An overstuffed payroll which got heftier this summer with the extension of Ristolainen and a trade for Tony DeAngelo points to a team that wants to win, but barring a miraculous season by Carter Hart or new coach John Tortorella (or both), they seem destined for the basement. Their cap situation may not be as dire as, say, San Jose’s, but the contradiction between team-building strategy and actual outlook is right up there.

22. Columbus Blue Jackets

Draft Capital: 6/10

Prospect Pool: 8/10

Age of Core: 6/10

Cap Constraints: 4/10

Competitiveness: 4/10

Columbus was humming along nicely in their rebuild, with a balanced core coming along of early-prime contributors like Patrik Laine and Zach Werenski and promising youngsters like Kent JohnsonCole SillingerAdam Boqvist, and David Jiříček. Then something funny happened: Johnny Gaudreau fell right into their lap. Add Erik Gudbranson, subtract Oliver Bjorkstrand, and things are looking real different.

The Jackets weren’t supposed to compete this year, and even with Gaudreau in the lineup it seems unlikely that they will. But while they probably don’t expect a Cup win in the near future, the need to maximize the remainder of Johnny Hockey’s prime will at least speed things along.

21. Seattle Kraken

Draft Capital: 8/10

Prospect Pool: 9/10

Age of Core: 5/10

Cap Constraints: 8/10

Competitiveness: 5/10

What to make of the Seattle Kraken? Let’s start with the prospect pool, which features the two players ranked first by EP Rinkside in the 2021 and 2022 drafts in Matty Beniers and Shane Wright. Not a bad start. How about their solid draft capital, with all their own picks plus two more second-rounders in 2023? Pretty good! Now factor in their capped-out payroll with several players signed into their thirties including Philipp Grubauer and Adam Larsson? Oh. 

The Kraken’s apparent commitment to at least trying to win in the short term has led to a fractured and unique outlook. Plenty of teams go through extensive multi-year rebuilds without ever drafting anyone like Beniers and Wright, but can the Kraken build around them? Their blue line lacks potential and youth which may be addressed through the draft, but the addition of Bjorkstrand and André Burakovsky directly responded to their biggest current weakness, suggesting that general manager Ron Francis would like to win. 

20. New Jersey Devils

Draft Capital: 6/10

Prospect Pool: 7/10

Age of Core: 5/10

Cap Constraints: 4/10

Competitiveness: 5/10

The Devils’ retool/rebuild has been difficult, constantly promising a change in fortunes that just won’t come. The summer of P.K. Subban and Nikita Gusev came to naught; adding Dougie Hamilton and Tomáš Tatar was undone by shoddy goaltending. But New Jersey has added two first overall pick centres and a second overall pick defenceman, a foundation that should at least give them plenty of cracks at this. With only nine NHL regulars signed after this season, the Devils have the flexibility to adjust if they once again disappoint, but Hamilton and Ondřej Palát signed through the front half of their thirties puts a bit more of a timer on.

19. Vancouver Canucks

Draft Capital: 6/10

Prospect Pool: 2/10

Age of Core: 6/10

Cap Constraints: 8/10

Competitiveness: 5/10

What is the direction of the Vancouver Canucks? It’s not clear exactly. Former general manager Jim Benning was fired after years of impatiently spending money on a team with dubious championship aspirations instead of rebuilding. Since he was replaced by Patrik Allvin, however, the Canucks have maintained course. They signed Ilya Mikheyev, extended Brock Boeser, and most notably extended J.T. Miller until he is 36-years-old. It is also expected that they will re-sign pending UFA and captain Bo Horvat. The true core of the team, Elias Pettersson and Quinn Hughes are in their early 20s. But the franchise seems focused on maximizing the short term, possibly at the expense of the middle- and long-term.

18. Winnipeg Jets

Draft Capital: 5/10

Prospect Pool: 5/10

Age of Core: 6/10

Cap Constraints: 6/10

Competitiveness: 5/10

I think it’s fair to say that most people expected a big shake-up in Winnipeg this summer. The stagnant and struggling Jets have a core that has been described as toxic and dysfunctional, with a roster built to win now that is not winning now. Connor Hellebuyck and Mark Scheifele are nearing 30-years-old, the standard bearers of a core that hasn’t quite worked since 2018. But they’re running it back at least one last time. In a happier situation, Kyle ConnorNikolaj EhlersCole Perfetti, and Pierre-Luc Dubois would be an excellent foundation for a dynamic young forward group, but it seems unlikely to emerge intact from the tumult to come. Meanwhile, an underwhelming defence core is locked in for the next few years. This group is theoretically all-in this year, but its outlook is so mediocre that it’s hard to even place that pressure on it.

17. Dallas Stars

Draft Capital: 4/10

Prospect Pool: 6/10

Age of Core: 3/10

Cap Constraints: 7/10

Competitiveness: 6/10

The Stars’ refusal to resolve the Jason Robertson stand-off (and lack of cap space with which to do it) makes this a tough situation to fully analyze, but the way this team is built is a bit strange anyway. A core of Robertson, Roope HintzMiro Heiskanen, and Jake Oettinger is enviable. Jamie Benn and Tyler Seguin signed above $9.5-million each until they’re 36 and 35? Not so much. That said, if they slowly but surely build out their depth around the star players, their contention window could stretch for several years in the future.

16. Nashville Predators

Draft Capital: 5/10

Prospect Pool: 5/10

Age of Core: 9/10

Cap Constraints: 4/10

Competitiveness: 7/10

Look, if I was a 72-year-old NHL general manager, would I be focused on building for the future? No, I would not. I would be trying to win a Cup before I retire. That is general manager David Poile’s plan, and he’s sticking to it. Filip Forsberg and Mattias Ekholm were excellent trade chips that could have fuelled a rebuild for a new era. Nope! Re-signed through their 30s along with Roman JosiMatt DucheneRyan JohansenMikael Granlund. Acquiring Ryan McDonagh was just the confirmation that the Preds are dead-set on winning with this core. Can they? Well, in a season where they enjoyed multiple career-high performances from star players, they grabbed the last wild-card spot and got punted out quickly in Round 1. So it doesn’t seem likely. But with only average future assets and an aging group locked in, they’re pretty damn close to all in.

15. New York Islanders

Draft Capital: 5/10

Prospect Pool: 3/10

Age of Core: 7/10

Cap Constraints: 9/10

Competitiveness: 6/10

Do you like the Islanders current roster? I hope so, because they’ll be around for a while. The Islanders have thirteen forwards, four defencemen, and a goalie from the 2020-21 Conference Finals roster under team control until 2024, a pretty stunning amount of consistency up and down the lineup. Their unexpected high pick in the 2022 draft was exchanged for Alexander Romanov, expected to slot into the top four this season. While the team has some younger core players like Mathew Barzal and Noah Dobson, the supporting cast is old and for the most part locked up for a while, putting plenty of pressure on the group to get back to the top. 

14. Minnesota Wild

Draft Capital: 5/10

Prospect Pool: 10/10

Age of Core: 5/10

Cap Constraints: 9/10

Competitiveness: 8/10

Is there a stranger team in the NHL right now than the Wild? Burdened with a whopping $12.7 to $14.7 million in dead cap for the next three seasons, Wild general manager Bill Guerin and Co. will need plenty of help from their elite prospect pool to remain in the hunt for the Cup while Kirill Kaprizov is in his prime and the older defencemen can still contribute. Matt BoldyMarco Rossi, and Calen Addison will be relied upon in the short term; Jesper WallstedtCarson LambosBrock FaberLiam Öhgren, and Danila Yurov will come into the mix later. Ideally, this team weathers their cap hell and comes out of it ready to hit another level, but for that to happen they will need either Jared Spurgeon and Jonas Brodin to maintain a high level of play or for the kids to take over on the blue line. 

13. New York Rangers

Draft Capital: 6/10

Prospect Pool: 5/10

Age of Core: 7/10

Cap Constraints: 9/10

Competitiveness: 8/10

While rebuilding teams languished outside the top-three of the draft lottery, the very briefly rebuilding Rangers enjoyed all the luck, coming away with Kaapo Kakko and Alexis Lafrenière in 2019 and 2020 and picking up Adam Fox for only a second-round pick. For most teams, adds like that would be the fundamental building blocks of a new young core, but for a team with players like Artemi PanarinJacob TroubaMika Zibanejad, and Chris Kreider locked in at the tail end of their primes, they’ve taken a back seat. It might be just as well, as neither player has yet shown flashes of franchise-level talent at the NHL level. The massive deals belonging to veterans entering or already in their thirties represent a ticking time bomb that could soon make life very difficult for the front office, so despite the promise of their youngsters they had better win quick.

12. Colorado Avalanche

Draft Capital: 3/10

Prospect Pool: 1/10

Age of Core: 4/10

Cap Constraints: 9/10

Competitiveness: 10/10

Nothing quite dials down the pressure of winning quite like taking home the sport's ultimate prize. The defending Stanley Cup champions have their core locked up long-term aside from Devon Toews, meaning the task ahead is to build the best and most cost-effective supporting cast possible. Getting to the summit meant emptying out the middle-round selections from the next two drafts, but the Avs still possess first-round picks that can be put to the task of getting back there. The young ages of Cale Makar and Bowen Byram may prove to be the factor that extends this team’s window the furthest, but it would undoubtedly be preferable to get the job done now before Nathan MacKinnon’s new deal slices an extra $6.3-million off of their cap space.

11. Edmonton Oilers

Draft Capital: 4/10

Prospect Pool: 2/10

Age of Core: 7/10

Cap Constraints: 9/10

Competitiveness: 8/10

Oilers general manager Ken Holland repeatedly emphasizes that he is not ready to go all-in on his team yet, but that time may be coming soon. The Edmonton core is squarely in their primes and the supporting cast is only getting older, as Zach HymanRyan Nugent-HopkinsEvander Kane, and new goaltender Jack Campbell enter their 30s with long-term deals. The late-2010s Pittsburgh Penguins and Washington Capitals have taught us not to be too pessimistic about contention windows, but the Oilers have not given themselves the flexibility that allowed both those teams to change course when necessary. The next two or three years will likely be their best shot at a Cup, and they have to maximize it. 

10. Vegas Golden Knights

Draft Capital: 5/10

Prospect Pool: 4/10

Age of Core: 7/10

Cap Constraints: 10/10

Competitiveness: 7/10

What do we make of the Vegas Golden Knights? Their supposed downfall has been much celebrated by a hockey world weary of their over-excited salary cap machinations and roster moves, but is the jubilance pre-mature? This is another team with two “generations” of core players, with Mark Stone and Alex Pietrangelo in their 30s and Jack Eichel and Shea Theodore a few years behind. The lineup looks pretty locked in, signed for several more seasons, assuming we don’t see the Knights once again make extravagant and unexpected trades. With a mediocre chest of futures, this team is built to win now and it had better get on with it.

9. Carolina Hurricanes

Draft Capital: 6/10

Prospect Pool: 6/10

Age of Core: 4/10

Cap Constraints: 6/10

Competitiveness: 9/10

No doubt, the Hurricanes are hungry to win. Now, if possible. They’ve been habitually foiled deep in the playoffs, and despite that have managed to renew their forward core with younger players while making aggressive moves for veteran contributors. It’s unfortunate that Max Pacioretty will miss the regular season, but he addresses their needs perfectly, as does Brent Burns -- at least in the short term. How “all in” is this team? Jaccob Slavin’s three years remaining on a laughably underpaid deal is a good indication of what their ideal window would be. But the emergence of some or all of Andrei SvechnikovMartin NecasSeth Jarvis, and Jesperi Kotkaniemi as legitimate stars would push it even further.

8. Florida Panthers

Draft Capital: 1/10

Prospect Pool: 3/10

Age of Core: 5/10

Cap Constraints: 9/10

Competitiveness: 9/10

The roller coaster ride the Panthers have experienced in recent years is reflected by the direction of the franchise. The team justifiably went all-in on their 58-win, Presidents' Trophy-winning squad last season and came up well short due to all of their forwards forgetting how to score against the Lightning. They reacted to that loss by letting their coach walk, hiring one with the opposite philosophy, and trading their leading scorer and second-leading defenceman scorer. The team is still built to win now, and with the exception of the goaltender, the core remains squarely in their primes. That’s key, because the process of getting here has left the team with the least draft capital of any team in the league. The next two seasons will probably be the best chance they get to win, but they’re not desperate… yet.

7. Washington Capitals

Draft Capital: 3/10

Prospect Pool: 1/10

Age of Core: 9/10

Cap Constraints: 3/10

Competitiveness: 7/10

With Alexander Ovechkin 37-years-old and Nicklas Bäckström’s career likely over, the Capitals have made savvy, light-footprint moves to keep the dream alive and preserve flexibility for the end of their window. Adding Dylan Strome and Connor Brown instead of pursuing a bigger name like Nazem Kadri may not fit the all-in mania being assessed here, and the Caps have almost $26-million coming off the salary cap next summer (with only six skaters signed, mind you), but the direction of the franchise is firmly pointed towards the here and now. Which is good, because the prospect pool and draft picks look unlikely to rescue them.

6. Tampa Bay Lightning

Draft Capital: 2/10

Prospect Pool: 1/10

Age of Core: 8/10

Cap Constraints: 10/10

Competitiveness: 10/10

It’s a bit easier to mortgage the future with a few Cup rings on your fingers. The Lightning have an empty prospect pool, one first-round pick in the next two years, and as good a shot as anybody at winning the Cup again soon. The core is locked up long-term, but what it took to do it is why the upcoming season is so important. Anthony CirelliMikhail Sergachyov, and Erik Černák all took sizeable raises which will only further constrict the already-airtight cap structure they’re running with. It’s a miracle that Alex Killorn has made it this far without being a cap casualty but it's hard to imagine that they’ll be able to bring him back in the fold again. Is this the last shot they have at the Cup? No, it’s not. But it’s certainly the best one, and with no more chips to push in they will have to make it count.

5. St. Louis Blues

Draft Capital: 4/10

Prospect Pool: 2/10

Age of Core: 6/10

Cap Constraints: 8/10

Competitiveness: 8/10

Some teams are all-in because they face a difficult cap situation, or because their players are aging out of their primes. The Blues are all-in because this team is likely going to look a lot different a year from now. Ryan O’Reilly and Vladimir Tarasenko, the superstars who led St. Louis to its first-ever Stanley Cup championships, will be unrestricted free agents this summer, and at 32 and 31 respectively with natural replacements in-house are unlikely to return. Does that mean the Blues are done competing? Probably not; despite a pricey and aging blue line, the younger core is encouraging and should be able to hold the fort fairly well. But it does make this a sort of last dance for this group at full power.

4. Calgary Flames

Draft Capital: 4/10

Prospect Pool: 3/10

Age of Core: 8/10

Cap Constraints: 8/10

Competitiveness: 8/10

Like so many teams in the league, the Flames stared down a fork in the road this summer and chose the gutsier option. Generally, losing two players like Gaudreau and Matthew Tkachuk in such quick succession would be taken as a sign to pull the plug, but Calgary took a look at their group and saw a chance to keep the party going. It meant getting a lot older; the 29-year-old Gaudreau and 24-year-old Tkachuk replaced by 31-year-old Kadri, 29-year-old Jonathan Huberdeau, and 27-year-old MacKenzie Weegar. There are helpful young-ish players on this team, but the writing is firmly on the wall -- win now. 

3. Toronto Maple Leafs

Draft Capital: 4/10

Prospect Pool: 4/10

Age of Core: 6/10

Cap Constraints: 10/10

Competitiveness: 8/10

The Toronto Maple Leafs have to win in the playoffs. Have to. Last season was the excuse year: “it was against the Lightning, we went to Game 7, etc.” But we’re at the end of the road here. Both Auston Matthews and William Nylander will be unrestricted free agents in two seasons, and there is no guarantee that they will return. This may be the final two seasons of this group’s contention before the start of another excruciating rebuild, and they have five years of failure behind them. The next three years of first-round picks are available to trade but, as usual, they can barely even sign a league minimum contract right now without going over the cap. Will their goaltending work out? It will have to. A failure even this season could inaugurate a new era in Leafs hockey.

2. Pittsburgh Penguins

Draft Capital: 5/10

Prospect Pool: 2/10

Age of Core: 10/10

Cap Constraints: 9/10

Competitiveness: 8/10

The Penguins have been in “win-now” mode for more than a decade now, and it’s served them pretty well. Despite rarely having blue chip prospects, Pittsburgh has kept their contention rolling and developing the guys they do have to play complementary roles. This summer could have been a turning point, the end of the Sidney Crosby/Yevgeni Malkin/Kris Letang era which has endured for sixteen seasons and the start of a rebuild. Not so. Not only did they extend the latter two players as well as veteran wingers Bryan Rust and Rickard Rakell, but they added 34-year-old Jeff Petry and 32-year-old Jan Rutta as well. This team is coming off a strong season and an impressive if futile performance in the first round last season, but there’s little doubt that they are the team most willing to sacrifice the future for the present.

1. Boston Bruins

Draft Capital: 3/10

Prospect Pool: 1/10

Age of Core: 8/10

Cap Constraints: 9/10

Competitiveness: 8/10

It didn’t have to be this way. One might have thought that a core of David PastrňákCharlie McAvoy, and Jeremy Swayman would be enough for the Bruins to transition smoothly into a new generation and keep their window wide open. But the team’s total failure to secure even a young top-six centre, let alone an elite one, has them relying on two veterans near retirement and facing the possibility that their star sniper might walk. Patrice Bergeron and David Krejčí are probably around for one last dance and then it’ll be a new era in Beantown, especially if Brad Marchand finally starts to show signs of age. Will the Bruins be doomed to rebuild after this year? Maybe not. But they are all-in on the end of this window.

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