My latest take on the Leafs (always changing):
Trade 1: Marner for Farabee, Laughton, 7OA (draft Reinbacher)
Trade 2: Nylander for Garland, Myers, 11OA (draft Danielson)
Trade 3: Brodie for Perron
Trade 4: Timmins for Kastelic
Trade 5: TOR 24 4th or NYI 24 3rd for Demelo
UFA:
Clifton 2Mx2
Rodrigues 3Mx3
I would explain why all the acquisitions make sense to me but I know no one will read it. The core philosophy of these moves is to take a step back for 2024 when the Leafs own their 1st round pick while setting the team up to compete for the next 5 years by getting younger (Farabee, 7OA, 11OA). The assumption is Matthews signs and agrees to this plan. The other assumption is you can't build a cup contender with Matthews/Nylander/Marner which has been proven true countless times.
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Myers is either 7D or AHL. Murray is also assigned to the AHL or LTIR'd. Murray, Myers, Perron expire next season and open up ~15.5M to spend in UFA on Pesce/Guentzel/Lindholm/Reinhart/Debrusk/Toews while potentially graduating Danielson and/or Reinbacher.
Edit: my plan has already shifted away from Clifton. Just trade for Demelo, ideally a 4th.