The offseason chatter in Pittsburgh, Montreal and Edmonton is heading in three very different directions, but each one has a clear contract or trade question hanging over it.
Start with Sidney Crosby, because that one sounds closest to getting resolved. Crosby is heading into the final season of his current deal, and extension talks with the Penguins are expected to happen before summer ends.
His agent, Pat Brisson, has not really begun the contract conversation yet, but the expectation is that both sides will get it done. Crosby is not talking retirement; the issue is simply how long the next contract runs.
The money, according to Yohe, should land in the familiar range - likely around Crosby’s $8.7M, since that is what he has been signing for with his jersey number - and could go higher if needed. The bigger decision is term, with one year or two the main question.
Pittsburgh’s first preseason game is Sept. 21, and the Penguins open Sept. 30 against the Flyers, so there is a real chance the extension is finished before then.
In Montreal, the Zachary Bolduc-for-Logan Mailloux trade is still sparking debate, but the bigger storyline now is Bolduc’s next contract. The Canadiens made the unusual July 1, 2025 swap, and early on it looked like Bolduc gave them the edge.
He scored in his first three games and finished with 30 points (12-18), though he also cooled off and posted a -6 rating. Mailloux had his own struggles, with limited NHL time, some adjustment issues, and a -10.
Bolduc remains a restricted free agent and has not signed yet, and his comments suggest he wants to stay in Montreal long-term while also not being completely sure where management stands. The Canadiens are weighing a bridge deal or a longer commitment, and the broader money climate around young players is only making that decision more charged.
Edmonton’s situation is more about what comes next on the trade front. The Oilers are expected to be in the market for another top-nine forward in 2026-27, but the list of possible targets will depend heavily on how the league sorts itself out.
A number of rebuilding or retooling teams could become trade partners, with names popping up from Vancouver to Pittsburgh. The Penguins look like a particularly natural match because of their winger options, including Rakell, Rust, and maybe Kuzmenko if they decide to sell.
Detroit could be the bigger swing if Alex DeBrincat becomes available. The Rangers’ Lafrenière, Vancouver’s Chytil or Drew O’Connor, and Seattle’s Wright or McCann are also names to watch.
Divisional trades, though, can come at a premium, which only complicates things for Edmonton.
In Other News...
Oilers Training Camp Battles Could Decide How Real This Cup Push Is
Training camp is still ahead, but the Oilers already have a few roster puzzles that could shape how serious this Cup push really is. On the back end, Spencer Stastney, Ty Emberson and Shakir Mukhamadullin are all in the mix for limited spots, and the outcome of that battle will say plenty about how Edmonton wants to build its blue line for the 2026-27 season.
Ike Howard is another name to watch as he pushes for a top-six role and could begin his camp path on the third line, giving the Oilers another layer of competition up front. The biggest uncertainty, though, may be in goal, where Frederik Andersen, Tristan Jarry and Stuart Levi are all part of the conversation and nothing has been settled yet, leaving Edmonton with one of those preseason decisions that can quietly define everything that follows. [Read more 🡒]
Oilers Linked To A Risky Scoring Bet With Serious Upside
Patrik Laine has long been the kind of scorer who can change the look of a power play in a hurry, which is why his name still carries real weight around the league even after the stops and starts of recent seasons. Drafted second overall by the Winnipeg Jets in 2016, he flashed elite finishing touch early and then ran into a long stretch of health troubles that have kept him from building much momentum, including a brief five-game run with the Montreal Canadiens.
For Edmonton, the appeal is obvious if the price and structure make sense. A player with Laines track record is the sort of low-floor, high-ceiling bet front offices kick around when they want offense without a long-term commitment, and his veteran status only adds to the calculus. The catch is obvious too, with teams expected to weigh his injury history heavily as they look at how to protect themselves in any deal. [Read more 🡒]