Now, ideally, this would be a second-round draft pick coming back to the Sharks, but the Leafs don't happen to have one until 2027, and that is just too far away to justify waiting for it. May as well pick up multiple draft picks and a good young player instead of waiting all that time for a second-round pick anyway. This is where I wanted to start with the idea of a Sharks goalie going to Toronto for a few reasons.
The big pull for the Sharks here is Nick Robertson. A young, talented forward, Robertson has been plagued with injury issues since he broke into the league a few season ago. San Jose would be a good place for him to try and come back from his injury concerns. Let him play alongside guys like William Eklund and Tomas Hertl and build his value up, and he himself could be a trade piece for the Sharks if they opt to go that route.
Ilya Samsonov would need to come back for a couple of reasons. First of all, the Leafs would need to do this to have the cap room for Kahkonen. But as a pending unrestricted free agent, Samsonov would be a good candidate to help the Sharks drop a few decisions that may be close with their current good netminders and ensure the best odds at picking first overall.
The two picks are for the combination of taking on Samsonov's deal as the second worst goaltender in the league by save percentage among all goalies to play in at least 10 games this season, and the upgrade Kahkonen is. I think this is the kind of deal that both teams would do very well from if it was made today. It would make both teams happier with the directions they are headed.