Others have discussed the possibility of a player like Phil Kessel being on the move, and the storylines that would come out of Phil the Thrill returning to Toronto would be nothing short of incredible, but as always, this is a dive into the less-discussed targets that might find their way onto Dubas' scouting report.
The right side is already quite full in Toronto, with Mitch Marner, Willy Nylander, Ondrej Kase and Wayne Simmonds there (with Mikheyev also having the ability to play the right side), but we all know about the health risks associated with Kase. They could also potentially look to upgrade over Simmonds on the 4th line if he should taper off down the stretch.
Dustin Brown
A long-time member of the LA Kings, Dustin Brown is in the final year of his 8-year, $47 million pact, which carries a cap hit of $5.875 million. Another player that would require significant salary retention and possibly a third team being involved to make the numbers work, but it might be worth it to bring in the grizzled vet. Stanley Cup experience, and 17 points in 34 games this season means teams will be taking a look. However, the Kings currently sit 3rd in the Pacific (the teams below them have games in hand) and Brown has a modified no trade clause (the player submits a 7-team no trade list as per CapFriendly).
This Vegas winger carries a cap hit of $5 million, however, with the arrival of Jack Eichel and his $10 million cap hit, Smith could find himself on the move, strictly because of financial reasons. Again, this would take salary retention (unlikely) or a third team being involved to make it work for the Leafs, but with 11 goals and 18 assists (29 points) in 39 games this season, Reilly Smith could be another offensive sparkplug for an already talented forward group. Also, his ability to play both left wing and right wing makes him a versatile add on the wing.
Cal Clutterbuck
The Isles right winger has netted 5 goals in 29 games this season, and no one ever really knows what's going on inside Lou Lamoriello's brain, but he could be on the move since his deal expires at season's end. With a $3.5 million cap hit, this could be a tough move financially for the Leafs, but one that could pay off, as Cal brings playoff experience from the Islanders' last two playoff runs, during which, they made the Eastern Conference finals.
Alex Chiasson
6'4", 208 lbs. Chiasson has just 6 points in 28 games for the Canucks this season, but the best part is he only carries a 750K cap hit. He also played 16 games during Washington's Stanley Cup run in 2018. If the Canucks cool off, or run out of runway after their bump by the hiring of Bruce Boudreau, they will likely be sellers at the deadline.
In the undersized winger category (we know Dubas has a tendency to acquire players of this ilk, Denis Malgin comes to mind) Danforth of the Blue Jackets fits the bill. With 2 goals and 4 points in just 13 games for the Jackets, he could raise some eyebrows. He's not a flashy name, but another 'bargain bin' component of this group. He also carries a $750K cap hit for this season. Pure depth option.
That's my look at the right wing market. Three positions down, 2 to go. Next up is the blueline group. Another identified area of need for the Leafs, let's hope there's a few more intriguing targets to be found.