With the news of a relatively flat cap again next off-season, let's take a look at where the Leafs stand. Currently, they have just 9 players signed for next season with a cap hit of approximately $70.74M. That would leave them just over $12.6M to fill out the remaining 14 roster spots. The Leafs have 8 UFAs and 7 RFAs that will need new contracts.
UFAs:Jordie BennWayne SimmondsPierre EngvallAlexander KerfootDavid KampfMichael BuntingZach Aston-ReeseJustin Holl
RFAs:Pontus HolmbergJoey AndersonDenis MalginConor TimminsMac HollowellIlya Samsonov
Obviously, the $12.6M won't be enough to sign all of the free agents so there will once again be a ton of new faces up front for the Leafs heading into next season, but a few UFAs the Leafs should prioritize are Kampf and Bunting while some of the team's RFAs, like Holmberg and Anderson, would be relatively cheap to re-sign.
The same can be said for the blueline where it would be highly unlikely that Holl returns as he appears to be in line for a hefty raise. That is not as concerning though with the acquisition of Timmins, who is an RFA and won't cost much to resign. The same can be said for Mac Hollowell.
The biggest cost during the off-season next year would be re-signing 25-year-old Ilya Samsonov, especially if he continues to play the way he has through the first quarter of the season. He could be looking at upwards of $4M per season a new deal, which would take up a third of the Leafs' available cap room.
Of course, re-signing a number of these players could be easier if the Leafs and Jake Muzzin remains on LTIR through the final year of his deal. That would give the Leafs an additional $5.625M, bringing their off-season cap space to $18.2M. The minimal rise in salary cap is not finalized and won't be until the end of the playoffs this season, so it could still rise more than $1M, but it does not seem likely at this point. The $1M rise would continue to put a number of teams under a cap constraint, not just the Leafs.