Which NHL Teams Have the Biggest Offseasons?

While some teams in the NHL are preparing for the postseason — you know, sharpening up skates, gassing up chartered planes, making sure everyone’s got their beards in line — others are on the couch, or the beach, already planning for next year. 

Beyond the teams already eliminated, there’s another crop of teams anxiously awaiting for what’s around the corner this offseason. 

Here are four NHL teams with the biggest offseasons ahead of them and potential road maps for each of them to have a successful summer. 

1. Chicago Blackhawks

Two years after selecting a generational talent, Connor Bedard, with the first overall pick, the Chicago Blackhawks are still completely lost. However, the fact that they have the Bedard clock ticking puts them at the number one spot. 

Just to summarize what decisions they have: they have a little over $30 million in cap space, a projected top-five draft pick, an ongoing head coach search, and a rising superstar who’s already beginning to show signs of impatience with the Blackhawks’ situation. 

To label this a make-or-break season for Chicago is 100% accurate. GM Kyle Davidson is not only general-managing for his job this summer but also for the state of the franchise in general. 

If they can’t find a way to improve their roster with the young talent they have in Bedard and up-and-coming defenseman Alex Vlasic, it’ll essentially waste the draft picks they used to get them. 

In free agency, they should re-sign Ryan Donato — it’s their only option after refusing to trade him at the deadline, and the continuity will be good for Bedard. They should try and make a run at Mitch Marner too and if they’re unsucessul, throw an overpay at Vancouver’s Brock Boeser.

With the projected top-five pick, they should ideally draft Boston College center James Hagens. Hagens seems to be falling slightly in draft projections after being the favorite for the number one pick for most of the season. If he can pay off as a prospect, he’ll spread some more depth around the lineup and create a lethal power play tandem with Bedard. 

For a head coach, they should go big or go home: get David Carle out of Denver. 

2. Boston Bruins

Like the Blackhawks, the Bruins are two years removed from a big moment in their franchise, the team’s best regular season. But those two years seem like decades when you look at where the roster is now compared to then and even more so compared to the start of this season.

Trading away Captain Brad Marchand was the biggest move of this year’s trade deadline, but Boston also dealt away mainstays like Charlie Coyle, Trent Frederic, and Brandon Carlo. The Bruins also spent a better part of the year with an interim head coach in Joe Sacco after firing Jack Adams winner Jim Montgomery. 

After all that, Boston dropped to last place in the Eastern Conference and is expected to pick in the top five in the draft. 

Boston’s offseason will go one of two ways: They either quickly load up on expensive free agents and try resuscitating this Pastrnak-Swayman-McAvoy core or take a more patient approach, signaling a longer and more extensive rebuilding period. 

Knowing the Bruins’ track record in past years, they’ll probably go for the first option. Is that the smartest thing to do in their current franchise situation? Probably not. But if Cam Neely and Don Sweeney are still in charge, it’s the way they’ve always done things.

If that’s the path they choose, I’d take a more radical approach to the lottery selection and see what it’s worth on the trade market. Don Sweeney is not good at drafting players — you could fill up a NHL contender with all the blue-chip players he’s passed on in recent years. But he’s usually very good at evaluating the trade markets and free agency. 

What could that top-five pick yield for Boston? It would need to be a top-of-the-lineup player for the Bruins to feel comfortable making that decision.

It’s hard to put a finger on what that player would be given that he’d likely be on a roster that gets bounced early in the playoffs that sees their team’s future going in a bad direction — think Ottawa’s Brady Tkachuk as a potential name. 

I think you’d then turn to the trade market and try converting Elias Lindholm into a young player or a draft pick, maybe attach Dean LeTourneau to the trade and upgrade your top-line center. 

For the head coach, throw whatever it takes at Mike Sullivan to get him in Boston if Pittsburgh decides to move on. 

In free agency, the Bruins shouldn’t try for a home run signing like Marner, especially given that the image of him in a black-and-gold sweater is unsettling. Sweeney should aim for singles and doubles, more cost-effective complimentary pieces who can build up the floor of the team.

3. Pittsburgh Penguins

The Penguins offseason really revolves around a simple question, do we want to be a Sidney Crosby museum or an NHL team?

The Washington Capitals this season proved this year, with Crosby’s main rival, that you should be able to still contend with an aging superstar at your core. 

Are there moves that the Penguins can make to put themselves in the same position that the Capitals are in this year?

Yes, but GM Kyle Dubas has thus far indicated that there’s no major shakeup coming to Pittsburgh. He’s content with keeping Crosby around, which makes sense, but also content to let Kris Letang and Evgeni Malkin stay as long as they want too. He’s also signaled that their head coach Sullivan is staying too. 

Even if they don’t touch any of that core, they have plenty of other levers to pull including a bevy of draft picks in the next couple of seasons, including their own first rounder and a conditional first-round pick from the New York Rangers this year. 

Dubas also has a strong relationship with the prized free agent Marner from their days together in Toronto. With $24 million in cap space, would they try a move that aggressive?

While all signs point to the status quo for now in Pittsburgh, they have the resources to make these last few years of Crosby’s career actually worth something. 

4. Toronto Maple Leafs

Alright, there’s only so many times you can mention a free agent before you need to talk about the team he’s currently under contract with. 

The Marner sweepstakes will be the defining story of free agency in the NHL and will likely define the kind of offseason that the Maple Leafs have. 

But beyond the 27-year-old’s impending free agency, what will Toronto do this summer if they fail to make it to the Stanley Cup once again?

I think they have a really good shot at getting there, but, also, they’ve had a pretty good shot at getting there for almost every season this past decade and they always fall short somehow. Without getting into any ‘definition of insanity’ cliches, how many more times can the Maple Leafs keep bringing out the same core, with a few minor tweaks, and expect different results?

These last few years have probably shown the starkest shifts after playoff eliminations, with the firings of their GM Dubas after losing in 2023 and their head coach Sheldon Keefe after losing in 2024. If they lose again in 2025, and potentially watch Marner walk out the door, what does Toronto decide to do?

With John Tavares’ contract coming off the books as well, they’ll actually have $26 million in cap space, plenty of room to make some significant additions and an opportunity to build a more well-rounded team around Auston Matthews and William Nylander. 

This isn’t to say that the best case scenario for Toronto is losing two of their top six forwards, but, that scenario gives them some interesting opportunities. 

If the Leafs lose early in the playoffs, or if they just fail to win the Cup, look for them to upgrade their defensive core in free agency and try to find someone more reliable in net. The goaltending market is a little dry this offseason but opportunities are out there for them via trade.