Ranking the retools: Canucks light years from Cup contention, Islanders trending up
Picture the scene.
A somber-looking executive stickhandles through an evasive press conference. The message to the audience is clear: the front office has lost faith in the roster’s ability to contend. Gasp. It’s time to ‘retool.’ The fan base has usually felt this way for a while, but this new direction promises a fresh start.
A retool is not to be confused with a rebuild — a long-term plan that involves dealing players for draft picks and prospects. And losing a lot of games. A retool is not to be confused with ‘running it back’ either — minor shakeup moves for optics that keep all the core players around. The Toronto Maple Leafs famously went this route for years.
Instead, retools attempt to take a small step backward in order to take more steps forward. With the trade deadline just more than a week away, it’s time to ask: do retools actually work?
🧰 Defining a Retool
A retool is a strategic shortcut.
It can be an honorable one where a front office isn’t willing to accept five to 10 years of mediocrity. A retool might be a commitment to stars that signed up to compete (i.e., the late Sidney Crosby-era Pittsburgh Penguins). Or where dedicated losing may not be in the franchise’s DNA. Retools can also be motivated by money. Ownership may want their arena filled — the Nashville Predators‘ last two decades, for example. Or because an organization is hamstrung from unmovable contracts.
But what is a retool, exactly?
- In January, we ranked 12 rebuilding teams. Long-term pain for long-term gain, in theory.
- Another 11 franchises entered 2025-26 in clear win-now mode, regardless of how it’s played out.
- The Calgary Flames were lost, waiting to see if last season’s 96 points were a fluke. Hint: they were.
- The remaining eight franchises were somewhere in between, deciding in recent years to renovate without tearing the walls down. That’s a retool. Short-term pain for any kind of gain.
We’re going to rank the retools on how likely each franchise is to win a Stanley Cup in the next four seasons. For rebuilds, we used seven seasons given the long-term nature of that cycle. But retooling teams are trying to make up for lost time, their core aging and having lost its way.
Sometimes, a retool is the best or only practical option. But if the approach doesn’t yield credible Cup chances, can it be a success? The risk of failing is significant. The franchise can end up with old, damaged parts, without having made draft picks high enough to bridge the generational gap.
So, in ranking these retools, we’re also going to answer a bigger question: does the strategy ever work?
8. Vancouver Canucks
General Manager: Patrik Allvin
Retool Started: January 2025
Biggest Move: Acquired Marco Rossi, Zeev Buium, first-round pick for Quinn Hughes
Other Moves: Acquired a first-round pick and Filip Chytil for J.T. Miller; replaced Rick Tocchet with Adam Foote; acquired picks for Kiefer Sherwood
Canucks fans could argue this retool was triggered by the Hughes trade in December, not the Miller trade. Vancouver did try to make the playoffs in earnest last season. But the Miller/Elias Pettersson saga took its toll, and jettisoning Miller felt like the first step backward. The package included a reclamation project and a pick — signs the front office was already in retool mode. Bringing in a rookie coach and having a quiet summer further demonstrated the franchise was not expecting Hughes would sign.
The Bottom Line: The Canucks won the 2023-24 Pacific Division, so stretching the core of Hughes, Pettersson, Miller, Brock Boeser and Thatcher Demko further was logical. Losing isn’t in gunslinging President Jim Rutherford’s blood, after all. But I’m not sure a team could feel further from the Stanley Cup right now. Elite talent is sorely lacking, nor is it on the way. Retooling sadly feels like a doomed half-measure.
7. Nashville Predators
General Manager: Barry Trotz
Retool Started: March 2025
Biggest Move: Drafted three times in first-round in 2025
Other Moves: Acquired a second-round pick for Gustav Nyquist; acquired Erik Haula, Nicolas Hague; Trotz announced plans to resign as GM
To call the period from July 2024 to the present day a disaster in Nashville would be a diss to disasters. There’s zero joy in any of it. A respected coach-turned-GM in Trotz will walk away from a roster featuring six players between the ages of 30 and 37 on lucrative, long-term deals with no-movement clauses. That Summer 2024 free agent frenzy that went all-in on an aging roster was the ultimate gamble. It backfired. With a 20% chance of making the playoffs, Nashville desperately needs to find a way to move their veterans.
The Bottom Line: Their prospect pipeline is solid — quietly drafting nine times in the first round since 2021 will do that. But their organization’s best talent either carries a fake I.D. or has a hair transplant guy in their contacts. It’s the cost of being a solid franchise that’s sincerely tried to make the postseason every year of the salary cap era. The Preds will rise again… it just won’t be soon.
6. New York Rangers
General Manager: Chris Drury
Retool Started: December 2024
Biggest Move: Traded Chris Kreider for a prospect and pick
Other Moves: Fired Peter Laviolette and hired Mike Sullivan; traded Artemi Panarin, K’Andre Miller, Jacob Trouba, Carson Soucy, Kaapo Kakko for futures; acquired J.T. Miller for a first-round pick and Filip Chytil
Drury’s letter to fans last month might have made it official, but his true retool began (and flopped) more than a year earlier. Trading captain Trouba was the start of an aggressive blast of trades of franchise staples. The goal? Reposition the Blueshirts in the playoffs sooner than later. He didn’t hire veteran, Cup-winning coach Sullivan or acquire J.T. Miller with dreams of winning the 2026 draft lottery. Like Vancouver, the Rangers had hoped a new coach and a few new faces would postpone a rebuild.
The Bottom Line: The Rangers’ public comments suggest they aren’t abandoning the core. But much of it has already been dismantled. Drury has cornered himself. Try to rush this (again) and New York won’t add enough to its modest pipeline. Move too slow and stars Adam Fox and Igor Shesterkin exit their primes. There’s a real possibility the only entertainment Sullivan catches on Broadway are the musicals.
5. Los Angeles Kings
General Manager: Ken Holland
Retool Started: 2025 offseason
Biggest Move: Acquired Artemi Panarin for prospect Liam Greentree
Other Moves: Fired Rob Blake and hired Ken Holland; traded Jordan Spence for draft picks; signed Corey Perry, Brian Dumoulin, Cody Ceci
After four straight first-round series losses to Edmonton, Hall of Fame executive Holland was brought in to rewire a frustrated franchise. But the summer was sleepy in L.A. Vladislav Gavrikov walked and they added a trio of slow-footed veterans. They announced 2025-26 would be captain Anze Kopitar’s final season. And after middling results to date, Holland made a shocking deal with the Rangers before the Olympics: #1 prospect Greentree for 34-year-old superstar Panarin. In for a penny, in for a pound. 12 years without winning a playoff round can lead to impatience.
The Bottom Line: When elite talent is available, teams without it need to pounce. But it feels like 3D chess to see Los Angeles beating Edmonton, Vegas, or the Central Division winner in a playoff series. While Panarin brings badly needed scoring touch, the Kings are now the second-oldest team in the NHL (30.0 years old on average). The retool hasn’t positioned them to Cup contend now… or in the future.
4. Pittsburgh Penguins
General Manager: Kyle Dubas
Retool Started: March 2024
Biggest Move: Acquired prospects and two draft picks for Jake Guentzel
Other Moves: Replaced Mike Sullivan with Dan Muse; stockpiled draft picks through trades; acquired Yegor Chinakov, Tommy Novak, Arturs Silovs through trades
During what would be a sixth straight season without a playoff series win, Dubas dealt Crosby’s go-to winger Guentzel in March 2024. It marked a true reset. The deal’s trade tree turned into a fruitful return. Dubas has had a brilliant run of finds in the last couple of seasons, extracting value from Chinakov, Novak, Silovs, plus bargain finds Parker Wotherspoon, Justin Brazeau, Anthony Mantha, and Blake Lizotte. Against all odds, the Penguins went from the obituaries to seventh in NHL points percentage (.625) at the Olympic break.
The Bottom Line: Dubas has done right by Crosby and pals, with strong odds of a playoff return. It’s been a nostalgic blast. But there’s a reason Pittsburgh isn’t higher on this list. Crosby is 38. Evgeni Malkin is 39. Kris Letang is 38. Erik Karlsson is 35. After that, draft steal Ben Kindel, 18, and a handful of decent prospects will navigate a tough talent gap when the Hall of Famers retire or fade.
3. Washington Capitals
General Manager: Chris Patrick
Retool Started: March 2024
Biggest Move: Acquired Jakob Chychrun for Nick Jensen and two draft picks
Other Moves: Acquired Logan Thompson for two draft picks; stockpiled draft picks through trades; signed Matt Roy
It’s easy to forget Washington had 111 points and won a playoff round last season. The Caps have transitioned this roster to a group in its prime — a critical retool ingredient for any hope of sustained success. Olympians Thompson, 28, and Tom Wilson, 31, plus Chychrun, 27, Aliaksei Protas, 25, and Dylan Strome, 28, will be around for a while to lead the post-Ovechkin era. Exciting prospect Ryan Leonard has arrived. Despite a clumsy season to date, Patrick deserves a lot of credit starting the retool early, being aggressive without mortgaging the future, and handing the keys to players with lots of tread left on their tires.
The Bottom Line: We’re six of eight teams into the list and both Washington and Pittsburgh are getting rave reviews. But is either team posing much of a threat to NHL heavyweights right now? It’s the perils of retools — even for the ones where GMs hit home runs, a lack of top picks clearly limits the team’s ceiling.
2. Boston Bruins
General Manager: Don Sweeney
Retool Started: March 2025
Biggest Move: Acquired a conditional pick for Brad Marchand
Other Moves: Traded Charlie Coyle, Brandon Carlo, and Trent Frederic for young roster players and picks; hired Marco Sturm to replace interim coach Joe Sacco; signed Tanner Jeannot
When captain and franchise icon Marchand, then 36, was moved last March, the former 135-point Boston juggernaut turned the page. This is the most classic of retools. The points by season visual above illustrates it nicely. The Bruins decisively shed cap space, got younger, and leaned in on under-30 stars David Pastrnak, Charlie McAvoy, Jeremy Swayman, and Morgan Geekie. Players without term left were dealt but for assets that could help fast — Fraser Minten, Casey Mittelstadt, Marat Khusnutdinov, plus draft picks.
The Bottom Line: Nearly 11 years into his GM reign, Sweeney has been given a lot of runway to land this plane. With 63% playoff odds, the jury is out on whether this Bruins core will contend again, but the execution of the retool in the last 11 months has been a smooth flight.
1. New York Islanders
General Manager: Mathieu Darche
Retool Started: March 2025
Biggest Move: Drafted Matthew Schaefer first overall
Other Moves: Acquired two first-round picks and Emil Heineman for Noah Dobson; acquired Calum Ritchie and draft picks for Brock Nelson; Lou Lamoriello stepped down as GM
There’s no sugarcoating that Lamoriello made some curious, long-term commitments that handcuffed the franchise. Gen Z will be in nursing homes before Pierre Engvall’s contract ends. But drafting Schaefer changed everything. Instead of a potential rebuild, Darche promptly dealt Dobson and leaned in on the core of Ilya Sorokin, Bo Horvat, Mathew Barzal, and Adam Pelech. The Islanders are greatly outperforming their underlying metrics and are dependent on Sorokin. But exceptional goaltending is part of their identity. New York currently holds a playoff spot in a shaky Metropolitan Division. So far, so good.
The Bottom Line: Schaefer’s immediate impact has unearthed exciting vibes on Long Island. The success of this retool in the short term will be tied to how long the core can stay healthy and elite. Lifting the Cup in the next few years still feels unlikely, but there is enough talent in the pipeline that this retool should transition neatly into a contender once Schaefer is winning Norris Trophies. That could be sooner than later.
🧰 Do Retools Work?
Entering the retool rankings, I’d hoped for light at the end of the tunnel. But the exercise didn’t find much.
The Canucks and Rangers are facing even longer roads to contention from their retools. Nashville and Los Angeles are elderly, with the Kings lacking a farm system. The Penguins have hit every possible retool note, but trying to win with legends nearing retirement is more inspiring than probable. Washington and Boston executed traditional retools quite well around prime-aged cores, yet both feel destined for a few years in the postseason mix without scaring anyone. The Islanders needed a draft lottery win for a generational defenseman — and they still might need another reset before contending.
Make no mistake: nearly all of these retools were defendable. Each has (or had) marketable stars, enough talent to dream, and no interest in tanking via teardown. Hockey is better with retools over rebuilds.
But if you’re Toronto, Winnipeg, or St. Louis this offseason, can you look around the NHL and honestly conclude that a retool is appealing? While success looks different to every franchise, retools are simply not bringing teams to Cup contention right now.
Data from Hockey-Reference; HockeyStats.com; PuckPedia; Elite Prospects
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