The Toronto Maple Leafs are in the middle of a rebuild, and the focus once again falls on Auston Matthews, who is expecting the roster to be strengthened. Recently, a shocking rumor emerged involving a potential trade with the Pittsburgh Penguins for one of Sidney Crosby’s teammates.

While there are several possibilities in the offseason, Matthews knows he will be the one leading the Leafs’ offensive power. At the same time, the Penguins are also going through a rebuild after several seasons of missing the playoffs. The two situations could line up for a solid trade.

The potential arrival of defenseman Erik Karlsson could represent a qualitative leap for Toronto on paper, but in practice, it seems like a complicated deal—especially after the comments made by former Leafs player Jay Rosehill, who weighed in on a possible trade involving Crosby’s and Matthews’ teammates.

An unviable trade

When asked about a potential swap between Karlsson and Morgan Rielly, Rosehill was categorical: “I don’t see anyone taking that deal,” the former Toronto player said in a conversation with Leafs Morning Take. At the same time, he clarified that he’d make the trade “all day.”

Erik Karlsson #65 of Team Sweden skates during the second period against Team Canada in the 2025 NHL 4 Nations Face-Off at the Bell Centre on February 12, 2025 in Montreal, Quebec, Canada. Team Canada defeated Team Sweden 4-3 in overtime.

“Morgan Rielly is stuck, he makes $7.5 million, and he’s no longer producing at the same level. To get the potential of Karlsson, who can run the power play, that’s a huge deal. In practice, though, it looks more like a pipe dream,” Rosehill added in a strong statement.

Big money in discussion

Proposing a trade under these conditions is not only ambitious but also extremely difficult to execute. A move of this magnitude would involve shifting more than $152 million in contracts, considering the long-term salaries of Karlsson and Rielly, along with their no-move clauses, which would complicate the deal even further.