3 big trades to shakeup the core:
To DAL: Matthews, Domi, Carlo
To NYI: N. Robertson, J. Robertson, Dumba
To TOR: Johnston, Dobson
To TBL: Nylander, McMann
To TOR: Cirelli, Bjorkstrand
To PHI: Woll, Cowan, Reaves (salary)
To TOR: Tippett, Hathaway
UFA:
Tavares+Marchand 12M (I am not sure if that's 4.5+7.5, 4+8, 5+7)
Raddysh 2Mx4
Tanev 2Mx4
Mangiapane 3Mx3
Perbix 2.75Mx4
Vladar 1.5Mx2
RFA:
Knies 6.5Mx3
Dobson 9.5Mx8
Knies-Johnston-Tippett
Mangiapane-Cirelli-Bjorkstrand
Marchand-Tavares-Raddysh
Tanev-Laughton-Hathaway
McCabe-Dobson
Rielly-Tanev
OEL-Perbix
Stolarz
Vladar
This leaves 2.86M for extras or if I'm off on salaries. The only UFA that feels like a stretch to sign is Perbix. All of Mangiapane, Tanev and Marchand have been heavily linked to Toronto. Tre signing Vladar if he deals one of Stolarz or Woll is probably a slam dunk.
If the Leafs can move out Rielly's money and bring in a better 2LD alongside Tanev that would be excellent. I do think pairing him with Tanev and giving him secondary matchups will help him a ton if he is not moved.