Summer dominoes: 10 major unresolved NHL offseason storylines

New Toronto Maple Leafs GM Brad Treliving foretold it on Day 2 of the 2023 NHL Draft a few weeks back when he addressed us at the podium and commented on the challenges of the salary-cap squeeze over the past several seasons.

“Five years ago, on July 2 you could hang the ‘Gone Fishing’ sign up,” he said, while predicting that teams’ offseason transactions would drag out longer into the summer than normal as they try to make the cap space work. 

Of our top 75 unrestricted free agents, 12 remain unsigned as we approach three weeks removed from the market opening. Several buzzed-about trade candidates have not changed addresses yet, and the odds of them getting moved seem to shrink as we inch closer to training camps.

Plenty of crucial dominoes have yet to fall so far this offseason – including one that has nothing to do with the salary cap. What are the top unresolved storylines as we drift into late July? Consider these 10.

1. The NHL’s 2018 Hockey Canada investigation findings

The bomb could detonate at any moment. The NHL is soon expected to release the findings of its investigation into the alleged sexual assault of a woman by as many as eight members of the 2018 Canadian World Junior Championship squad. When the findings are released and names are named, suspensions from the NHL will likely follow – and criminal charges could, too, depending on the London Police investigation. It’s already one of the darkest stories in hockey history, and the wound will reopen once we know the identities of those facing the allegations. The repercussions could be unprecedented given multiple star-caliber players on current NHL rosters played on the 2018 WJC squad. But please: When the results finally do come out, let’s remember to acknowledge and prioritize the pain and suffering of the victim before considering the hockey implications.

2. The Erik Karlsson trade

The San Jose Sharks will never have a better selling window for their $11.5 million defenseman than right now, when he’s fresh off a legendary season in which he won his third Norris Trophy, became the first blue-liner in 31 years to reach 100 points and, just as importantly, played all 82 games. Karlsson, 33, has also publicly stressed his desire to get moved to a winning situation. The reporting at the moment continues to suggest the Pittsburgh Penguins and Carolina Hurricanes are the front-runners to execute a Karlsson trade. To editorialize for a second: I don’t see the hockey fit. Do you need an right-shot, all-offense PP1 quarterback when you have Kris Letang and Brent Burns, respectively? But to each their own. If Sharks GM Mike Grier is willing to eat a significant enough chunk of Karlsson’s salary over the final four seasons of his deal, a trade still feels likely to happen before the 2023-24 campaign commences.

3. Auston Matthews’ & William Nylander’s contract extensions

Have you heard? Two of the Toronto Maple Leafs "core four" forwards are 2024 UFAs. The story gets about as much press as "Barbenheimer" in these parts. The good news for Leaf fans: The mood around Matthews’ negotiations continues to be positive. He’s expressed his desire to remain in Blue and White, and as reported by Sportsnet’s Elliotte Friedman earlier this week, a medium-term deal in the range of three to five years is the most likely outcome. For Matthews, it feels like a matter of when, not if, but the vibe around Nylander is far different. First, there’s already the precedent for his camp letting things go down to the wire, as it did when he signed his previous contract on Dec. 1, 2018, hours before the deadline to play in the 2018-19 season. Secondly, Nylander indicated after the season that he wasn’t in a rush to sign. Then came the report from TSN’s Chris Johnston that his asking price could land in the $10 million range. This week: Friedman indicated Nylander and the Leafs “aren’t close” in their negotiations.

If Treliving isn’t confident that he’ll find a middle ground with Nylander, the Leafs must stare down a difficult decision: Do you cash out Nylander now, perhaps in a trade for a top-four defenseman, to ensure you don’t lose him for nothing? Or, given how important he is to the team’s current Stanley Cup hopes, do you treat him as an “own rental” and take your chances that you can sign him by next summer?

4. Patrice Bergeron’s and David Krejci’s retirement decisions

Earlier this offseason, the Bruins indicated they were proceeding as if their top two centers were retiring. Are we sure about that? So far, Boston’s summer has consisted of (a) waiving goodbye to UFAs Tyler Bertuzzi, Dmitry Orlov, Garnet Hathaway and more; (b) trading Taylor Hall and Nick Foligno in a salary-dump move; (c) signing defenseman Kevin Shattenkirk, left wingers James van Riemsdyk and Milan Lucic and center Morgan Geekie. Given Geekie projects to fill a bottom-six role, it’s clear the Bruins are doing the opposite of moving on from Bergeron and Krejci. The Bruins are holding their breath, waiting on the decisions to return or retire. If Bergeron and Krejci choose the latter, the Bruins will have a crater up the middle. It would necessitate a trade to fill it. Otherwise, the likes of Pavel Zacha and Charlie Coyle will play much higher in the lineup than they have in the past, and the Bruins lineup depth will be badly depleted entering 2023-24.

5. Vladimir Tarasenko’s landing spot

It appeared Tarasenko had put pen to paper a couple weeks ago, when reports surfaced of him signing with the Hurricanes. Whatever may or may not have been developing between Tarasenko and the Canes fell through. He fired agent Paul Theofanous and reset his courtship to square one. Now under the CAA umbrella with super-agents Pat Brisson and JP Barry, will Tarasenko still end up on a Canes team seemingly hellbent on winning a Stanley Cup in 2023-24, or is the door now open to another team, such as the Ottawa Senators, who recently cleared cap space with their trade of Alex DeBrincat to the Detroit Red Wings?

6. Tickets out of Winnipeg for Connor Hellebuyck and Mark Scheifele?

The Jets entered the 2023 offseason with a bad aftertaste. They bowed out in a five-game loss in the first round of the playoffs, after which coach Rick Bowness called out his star players for a lack of effort, after which veteran Blake Wheeler called out Bowness for those comments. It wasn’t a massive surprise to see Wheeler, the franchise’s all-time scoring leader, bought out. Nor did it raise eyebrows a few days before that when the Jets sent Pierre-Luc Dubois to the Los Angeles Kings in a blockbuster trade. It was common knowledge that Dubois didn’t plan to sign an extension in Winnipeg, but there’s still meat on the bone for GM Kevin Cheveldayoff. What about star goaltender Connor Hellebucyk and No. 1 center Mark Scheifele, who enter the final seasons of their contracts?

The deeper we get into the offseason and the more teams wrap up their spending, the less likely it seems we’ll see the Jets make additional trades. Several of the teams who could’ve been in the market for a new No. 1 goaltender – the Kings, Carolina Hurricanes, Ottawa Senators and Pittsburgh Penguins – signed new starters or retained their old ones. What if the market for Hellebucyk has dried up? As for Scheifele, a $6.125 million cap hit isn’t the easiest to move. Is it possible a team like the Bruins is waiting on Bergeron and Krejci before deciding whether to pursue help up the middle?

With each passing day this summer, the odds increase that we see Hellebuyck and Scheifele still suiting up for the Jets in October. If they do and remain unsigned for 2024-25, they’ll be talked up as in-season trade candidates if the Jets aren’t contenders next winter.

7. What’s next for Patrick Kane and Jonathan Toews?

The longtime Chicago Blackhawks’ future Hall of Fame duo find themselves wandering the desert as UFAs for the first time. When might we see them put pen to paper on new contracts? Kane, who fizzled as a New York Rangers deadline rental, is reportedly waiting out the four- to six-month recovery timeline on his hip resurfacing surgery before signing a new contract, so he might not choose a team until partway through the 2023-24 season. As for Toews? As previously reported by my colleague Frank Seravalli, Toews hasn’t decided if he even wants to play hockey anymore after long COVID put his body through the ringer over the past few seasons.

8. Evan Bouchard’s contract extension

It wasn’t a surprise to see Bouchard’s game blossom after Tyson Barrie vacated the Oilers’ top power-play quarterback spot when he was included in the trade with the Nashville Predators that brought Mattias Ekholm to Edmonton, but Bouchard leveled up even further in the playoffs. With 17 points in 12 games, he had the highest playoff points-per-game mark (min. 10 GP) of any defenseman this century aside from Cale Makar in his 2021-22 Conn Smythe Trophy run. As the Oilers do some salary-cap tapdancing, Bouchard is expected to sign a bridge contract in the two- or three-year range. What will the average annual value be? Bowen Byram and K’Andre Miller may have set the bar earlier this summer with their two-year bridges, signed with the Colorado Avalanche and New York Rangers, respectively, at AAVs of $3.85 million and $3.872 million. The Oilers have $5.6 million in cap space at the moment and have to allocate it between Bouchard and RFA center Ryan McLeod.

9. Will the Philadelphia Flyers’ fire sale continue?

It felt like 2023 would be the summer of Danny Briere, and it has been to a point. The new Flyers GM came out firing in June when he traded his No. 1 defenseman in Ivan Provorov and No. 1 center in Kevin Hayes. Then came the Tony DeAngelo buyout last week, but the potential trades of right winger Travis Konecny, defenseman Travis Sanheim and goaltender Carter Hart, among others, haven’t materialized. As previously reported by Seravalli, teams have trepidation over acquiring Hart until the 2018 Hockey Canada investigation findings come out. As for the other key Flyers potentially changing addresses: The Flyers rebuild is in its infancy, so Briere likely isn’t brimming with urgency. He doesn’t have to trade every last piece in one offseason.

10. Fate of the Calgary Flames’ big-ticket 2024 UFAs

The PR was pretty disastrous in the weeks following Flames’ regime change as Craig Conroy took over as GM. Even with taskmaster Darryl Sutter out as coach, 2024 UFAs Tyler Toffoli, Elias Lindholm, Mikael Backlund and Elias Lindholm all expressed their intention to leave next summer. Conroy traded Toffoli to the New Jersey Devils, but Lindholm, Backlund and Hanifin remain Flames. Will that be the case to open the 2023-24 season? It’s beginning to look that way. If the Flames slide out of the playoff picture again next winter, Conroy could rule the trade deadline with the assets he’d have available, but could the right offer still come along this summer? It might depend on how some of the aforementioned dominos fall, including the Bruins centers and Nylander’s contract talks.

Other storylines to watch…

• Elias Pettersson’s contract extension
• Sebastian Aho’s contract extension
• Vince Dunn’s contract extension
• Will the New York Islanders trade for a veteran scorer?