Of course, this isn't to say that Nylander would be dealt to San Jose, because the Sharks could very well be one of the teams on Nylander's 10-team no-trade list. If that's the case, the Leafs would first have to find Nylander a new home, opening up nearly $7M before they could commit to bringing in another big ticket player like Karlsson, even at a reduced $9.2M cap hit. The Leafs would also have to make a subsequent move to become cap compliant, which could involve moving
T.J. Brodie to open up a spot in the lineup for Karlsson as well. To be clear, I'm not suggesting that Nylander and Brodie will be moved, I'm simply discussing some of the options that the Leafs have to open up the space that they would need to pursue such a trade.