What the Leafs Need:
The Leafs need a star winger to make their offense untouchable, and they need an impact defender to play in their top four.
Alex Kerfoot is a good player, but he’s at the top of his game and his value will never be higher. Selling high on Kerfoot, trading Nick Ritchie, and trading Justin Holl will create $6.875 million dollars to spend.
(Note that this info is from capfriendly.com, and includes the money it’s costing them to have Nick Ritchie in the minors, not his actual full contract).
If you add that to the money that Cap Friendly projects them to have available at the deadline, they could have $9.5 million dollars to spend, which is probably enough to get two impact players.
What the Leafs Will Do
The Leafs will create cap space by trading Alex Kerfoot and Justin Holl for some picks and prospects. They likely would only be of interest to a playoff team, meaning it is unlikely they would be part of a package to bring in what the Leafs need.
They will find a team to take Nick Ritchie without retention or paying to make it happen. You will never go broke betting on an NHL team to give another chance to a player who is tough and has draft pedigree.
After that they’ll be looking to land some big fish.