There is a challenge in being "shrewd", in that if not done correctly, you get yourself backed into a corner.
Take Nylander as an example. His comparables were all in the $8.5-$10m range. They could have traded him to any of the 31 other teams in the league. Instead, they waited, NMC kicks in, he started off hot, and inexplicably, he's being paid $11.5m x 8 years.
With Marner, they're in a VERY difficult position. He holds all the cards and the Leafs seem perfectly willing to "let the situaton play out".
There's only 3 possible outcomes for this... you trade him in the offseason, or either you let him walk as a UFA, or you cave and give him another exorbinant contract.
Both of the latter two are lose-lose situations.... especially considering a quick look at the UFA list for 2025. His $11m is probably going to go pretty quickly to some unspectacular players.