Let’s start with this disclaimer. Sidney Crosby probably won’t be traded. He has a no-trade clause with one year left on his contract, and if he leaves the Pittsburgh Penguins, it’s his own doing. A trade will only happen if he wants one.
Ideally, Crosby isn’t traded, and he’s around to see the Penguins not only rebuild but also get back to contention. Here’s the problem: that might take some time, and Crosby, at 39 years old, doesn’t have many years left in him (although based on how players are aging, 40 might be the new 30).
The question is whether Crosby prefers to stay loyal to the Penguins or to end his career on a contender and with another Stanley Cup. The Cup won’t happen in Pittsburgh. So, if he wants to finish his career on a contender, there are a few teams he can demand a trade to.
Scenario 1: Crosby to New York Rangers
Whenever a star is available, the New York Rangers, by default, are part of the conversation. Mark Messier, going from the Edmonton Oilers to the Rangers, is a prime example and set the tone for other skaters to follow.
It’s worth noting that winning in New York is different. The high of winning in the market is unlike others, and it’s why Crosby could be intrigued with bringing a Cup to the Big Apple.
The Rangers also make a lot of sense from an on-ice perspective. Mike Sullivan coaching the team makes for an easy connection. Plus, the Rangers, while not contending at the moment, have the pieces to do so, notably with elite goaltending from Igor Shesterkin. So, Crosby can join the team and immediately put them in the Cup conversation.
Scenario 2: Toronto Maple Leafs
For as big as winning in New York is, winning with the Toronto Maple Leafs is on a level of its own. Crosby is already an icon in Canada, leading the nation to two gold medals and scoring the golden goal in the 2010 Olympics. Imagine if he ends the longest Cup drought in league history.
If the Maple Leafs find a way to acquire Crosby, they might be acquiring a player who is one-and-done. He’ll join the team for one run at the Cup and then sign elsewhere or retire. That said, it’s worth it if he gets them the Cup. Also, it’s fun to see a world where Crosby is playing on the same line as Auston Matthews while the Maple Leafs battle against the Florida Panthers.
Scenario 3: Edmonton Oilers
There are two things to consider with the Edmonton Oilers and their hopes of getting Crosby. One, they must make a case for Connor McDavid to stay, and the best way to do that is by going all-in on this season. Two, they are the only team that can also acquire Tristan Jarry with the hopes of fixing their goaltending for the playoffs.
For the Oilers to make this happen, they must jump through hoops, especially if they also acquire Jarry. They don’t have any cap space or assets, two things that will prevent them from being in on the sweepstakes.
If the Oilers make the space, whether it’s with a trade or having the Penguins retain salary, then they become an interesting spot. McDavid, Crosby, and Leon Draisaitl playing together seems like an impossible trio to stop.
Scenario 4: Colorado Avalanche
The Crosby-McDavid duo would be fun to watch but the Crosby-MacKinnon duo makes more sense. Nathan MacKinnon grew up idolizing another Nova Scotian star in Crosby, and they can play alongside each other next season.
If there was any team Crosby would want to finish his career with, it’s the Colorado Avalanche. They are a perennial contender, and he can play alongside MacKinnon. They don’t have many pieces to trade but they can end up being the only team Crosby wants to play for, giving them more leverage.
There is one other team to keep in mind. The Avalanche are a good spot but there’s one team that Crosby might want to end his career with and put a stamp on his legacy if he can’t do it with the Penguins.
Scenario 5: Montreal Canadiens
The Montreal Canadiens are a sleeping giant. They are a team in a market that can take off and be the next dynasty in the NHL. Once the Canadiens become a contender, and they are starting to enter that conversation, they can be a juggernaut for a while.
They also have a ton of assets to move to get Crosby as well. The Canadiens can offer the Penguins top prospects like David Reinbacher and Owen Beck and still keep their young core together. The Canadiens can also add in a first round pick to sway the Penguins, who will look for as many pieces possible to rebuild.
This can open the door for Crosby to finish his career with a Canadiens team on the rise. There would be something fitting about Crosby finishing his career in Montreal. The team that has 24 Stanley Cup banners hanging in Belle Center (or Centre Belle as it’s more commonly called) can become the next dynasty, with an icon being the one who kickstarts it.
Beyond Silly Season: The likeliest Crosby scenario
Mid-July is a fun time to pass the Offseason with hypothetical scenarios. But we’ll close this where we began. In all likelihood, Crosby is a Penguin to stay.


