If Hamilton isn't interested in re-signing with Carolina...
Trade #1
To Toronto: Hamilton (extended), Reimer
To Carolina: #15, Liljegren, Anderson (extended)
Toronto get a hometown #1 RD
Carolina get a #1 goaltender, a young Dman with some upside, plus the #15 pick in a strong draft
Trade #2
Toronto out: Johnsson, Kerfoot, Reimer
Toronto in: Hogberg
Buffalo out: Mittelstadt, Okposo
Buffalo in: Johnsson, Kerfoot, Anisimov
Ottawa out: Anisimov, Hogberg
Ottawa in: Mittelstadt, Okposo, Reimer
Toronto clear the necessary cap space to sign Pietrangelo
Buffalo get some serviceable forwards to help fill out their roster, while also dumping Okposo's contract. Anisimov's contract expires next summer, so he'll be off the books by the time Dahlin's extension kicks in
Ottawa land a young C with some upside, plus a solid goaltender whose base salary is only 850k for next season who can hopefully be flipped at the deadline. Okposo's salary will help them reach the cap floor for the next few seasons while they're rebuilding, but he'll be off the books by the time this year's draft picks are due for extensions
Assuming Pietrangelo wants to play for the Leafs, their defense next season...
Rielly - Pietrangelo
Muzzin - Hamilton
Sandin/Dermott/Holl