Hindsight signings of the big 3

Team: 2020-21 Toronto Maple Leafs

Initial Creation Date: May 16, 2020

Published: May 16, 2020

Salary Cap Mode: Basic

Here is the rational...

Matthews: Matthews camp clearly wanted a 5 year term. They wanted two kicks at the can to cash in give him options at 27. 5 years doesn't buy any UFA years and at the time Matthews numbers, although impressive, were not quite "Elite" even though it was obvious he would soon get there.
Dubas could have said we are giving you Tavares' number because our culture is about "team" and not about 1 player being "the guy".
11 x 5 is a great deal for Matthews and it works for the Leafs. It is still a good enough offer that even if someone tried to offer sheet, the offer wouldn't have been big enough to sway Matthews away.

Nylander: The contract was fine. The way it was allowed to be signed was not. If you're the GM of a team you need to establish an appropriate culture. In this case, the word to Nylander needed to be "Here is 7 x 6, that is our final offer." We really want William on this team and you have every right to negotiate the best possible deal, but this is it. If the deal isn't signed by Oct 1st, he will sit out the season. No team in the NHL was going to beat 7 x 6 via offer sheet. Any more than that and the compensation would be 2- 1st rounders, 1- 2nd rounder, 1- 3rd rounder.

Marner: This was probably the biggest overpay and in my opinion was a simple case of a big bluff from Marner camp and Dubas fell for it a little.
Marner had a good argument, using Tavares and Matthews as comparables and threatening with offer sheets. The reality is Marner was going to be a Leaf. He wasn't going to sign an offer sheet with CLB or NYI. And if he did, you have to accept that. If a team was willing to make him the highest paid player in the NHL there isn't much you can do about that.
So.. Similar to the Nylander situation. You offer 10 x 6 which is still technically a slight overpay based on comparables and you say "You have until Oct 1."
He would sign. And if he didn't you could either match an offer sheet that would likely be cheaper than his current contract or you take the 4 1st rounders.

All in all I think Dubas did a good job. He identified his core guys, he promised to sign them all and he did. Obviously its pretty clear he could have signed some of them for cheaper. My analysis is that he could have saved about 1.5-2 mill between the 3 of them. Those who suggest he could saved 4+ mill are being ridiculous.

Thats my take