Wait! I thought it was about the length of the contract, 4yrs vs 5? Now it's about the money? LOL.
If I were Jerry I would do $40 million for 6 or more years, and around $100 million guaranteed. Then I could structure the contract to give Dak a big bonus up front and backload the salary so it is CAP friendly the first couple of years and the worst of it would hit when he CAP is up around $220 million. In two years the Cowboys can unload some unfavorable contracts creating room for Dak and other players.
But $40 million for 4 years? No way. First, I don't want to go through this process again in 4 years. 2nd, Dak is not worth $40 million now and probably won't be in 3 years. I like Dak and wish they had him signed already. But players come and go. I root for the team. Dak is a good QB, not a great QB. He does not deserve great money. I want a team around my QB (I think we need a team around Dak) and paying Dak $40 million over 4 years really hamstrings the team CAP-wise. I'd offer Dak $36 million for 5 years, then franchise him when he says no, then trade him for 2 first round picks. Then I can use my #10 pick on a QB or maybe trade up for a better one.
I do believe the problem with the Cowboys is and has been the defense. Once they have a dependable defense, a defense that can stop late drives, take the ball away, force mistakes, etc. and they don't have to depend on the offense to be perfect so much, a young QB can be successful with the offense they have.