Quoting: dgibb10
Bc he's an aging player with the third highest contract of all LWs.
Meanwhile there's at least 15 LWs I'd take over him.
Nico hischier meanwhile has the 33rd highest C contract (might go lower), and there's also only about 15-20 Cs I'd take over him
You're mesmerized by cap hits. The analysis of whether a contract is a "bad" contract involves a three-variable equation: cap hit, actual salary, and performance.
The fact that Benn's cap hit is the third highest of all LWs is utterly irrelevant to the issue of whether it's a good contract or not, as a nanosecond's worth of thought should establish: Connor McDavid has the highest contract of all centers, and David Pastrnak's new contract will be the highest among all RWs. If they perform the way we know they do and will, who cares?
Let's start with some basics, founded on what you yourself have said: Hischier is an excellent player. He is "just as good production-wise" as Benn. He costs more than Benn, despite his cap hit. Hischier is younger than Benn, and will probably become more productive in the future than he is now, while Benn will probably regress with age. Now, what are we to conclude from these accepted facts?
(1) Despite the fact that Hischier plays a more productive position, and plays on the first line and thus gets more playing time on ice than Benn, he isn't outperforming Benn. Now, no one with an ounce of knowledge about hockey would say that Hischier's contract is a "bad" one, so how can you argue that Benn's contract is a bad one?
(2) The fact that a contract may age badly as the player ages doesn't make the contract a "bad" one now; I recall more than just a couple of players named Chelios and Chara that played pretty well into their dotage.
(3) The fact that you, and probably I, would take one player over another is utterly irrelevant as to the issue of whether one player's or the other's is a "bad" contract.
Let's take some examples:
(1) Player A has a cap hit of $8 million and a real salary of $6 million. Player B has a cap hit of $6 million and a real salary of $8 million. They have the same number of points. Who has the "bad" contract?
(2) RW "PK" has scored 50 points in 61 games and has a cap hit of $10.5 million with a real salary of $6.9 million. RW "PL" has scored 48 points in 53 games and has a cap hit of $8.7 million but has a real salary of $9.1 million (i.e., 50% more). Who has the "bad" contract?
Cap hit is merely a fact -- a factor to be considered in the calculus of "good" vs "bad." Production in light of cap hit and actual salary is truth.