Dubas got played last time by Matthews agent Judd Moldaver, when Matthews received one of the leagues highest AAV and Cap Hit % and only needed to sacrifice 1 year of UFA status to achieve it when the entire league knows he should have been locked up for 8 years at that rate. That is why we find ourselves in this situation here to begin with.
However if you look at cap increase projection in the upcoming years they're suggesting + $4 mil increase in 2024 and then +$4.5 mil 2025 with a ceiling up to $92 mil at that point, and + $9.5 mil from this season.
Even If Matthews locks himself in for 8 years now even at 17% CH or $15 mil per AAV, the cap increasing so dramatically that his contact would be undervalued in just a few seasons. So I'm guessing Matthews agent uses the same strategy he did last time and gets Auston a shorter term ~ 3 year deal at $ 15 mil (which should have been already included in his last deal), and then when the cap increases again dramatically by the end of its term we might be looking at a $100 mil cap ceiling.
$15 mil of a $100 mil ceiling is 15% Cap hit %. However if he double dips in 3 years back up to 17% it adds a cool +$2 mil per years AAV from $15 mil to $17 mil and makes sure Auston remains among the highest paid players in the game. The only way otherwise is to give Matthews his $16-17 mil AAV or near 20% on his next deal.
ie MATH
Option #1 : 3 years @ $15 mil (17% CH%) + 5 years @ $17 mil (17 CH%) = next 8 years = $130 mil deal over 2 contracts
or
Option #2: 8 years @ $15 mil (17% CH% ) = $120 mil total (- $10 mil less)
or
Option #3: 8 years @ $16.25 mil (18.57 CH%) ( based projected cap in 2024 @$87,500,000) = $130 mil (same gross revenue for Matthews as Option #1)
By doing 2 shorter term bridge deals (Option #1) = 8 years Matthews at 17 CH% can say he is leaving money on the table by not taking the max 20% but still maximize his earnings over that time while in turn guarantees his contract remains relevant and among the highest in the league. Option #2 leaves $10 mil on the cutting room floor for Matthews in lost wages & Option #3 sets Matthews AAV and Cap Hit % at 18.57 which is the worst option for the Leafs over the 8 years. Thus making Option #1 the best for both sides !!!!
Leafs might want Option #2, but Matthews might only agree to Options #1 or #3 and as a UFA he knows very well if the Leafs don't give him what he wants there will be other teams that gladly will.