The Reaves signing was ridiculously bad... he's signed until he's 40, and not on a contract that can be fully buried.
Klingberg, Bertuzzi, and Domi are al fine signings in isolation; but are repeats of the same problem -- which is taking the "core 4" and recycling depth chairs around them -- the "2 tier class" of the Maple Leafs. The fact that they're all 1 year deals, screams just how obvious Treliving & co view this.
Luke Schenn was a tough loss, but he's not a good buy at $2.75m X 3 year defenceman at 33 years old. No hard feelings there, and you have to wish him the best.
ROR is tough. Presumably, the Leafs had a very similar contract offer to ROR on the table; and the fact that a winner like that chose Nashville over Toronto should be a black mark on this organization. Nashville has $9m in dead cap this year, and over $11m in dead cap next year.
You walk into NMCs for Marner & Matthews, without a contract in place for Matthews. That's a problem and now risk allowing history to repeat itself with what Johnny Gaudreau did to Calgary. As for Nylander, his 10-team NTC isn't the end of the world; although with everyone having spent their money now, a deal could be tougher.
My biggest question(s).... you know John Tavares is a potential issue at #2C...what did you do to address that? Tyler Bertuzzi isn't a centre. Is Max Domi one? Who's the #3C on this team?
Sign John Klingberg that's great, but you also had a need for size and some tenacity on the blueline.... where's that coming from?