You would make a good player agent.
This is exactly the Matthews strategy that Jake Moldover Auston's agent is attempting to deploy against the Leafs to get his client maximum earning potential in his career by coming up to the re-sign window often and scoring big each time, while raising the market ceiling for others which the NHLPA would love also. It already worked once on Leafs last GM and now they're about to try it again on the next one.
Paying Matthews anything he wants with no red line might be great for HIM, but what about the Leafs team?
Each time he re-signs he increases his C.H% and his AAV and reduces the amount of cap space for others and as such lowers Cup competitiveness for the Leafs team in the process by eating up a bigger slice of the salary cap pie.. What is the good of having star players if financially it prevents the team from winning?
There is a direct correlation between Leafs having no red line and having 3 of the 7 highest AAV contracts and also Leafs as a franchise having the worst playoff record and least success due to those spending habits.