Best window doesn't really mean championship or even NFCCG. The other teams at the time have to be taken into consideration but there has been this thought that having Garrett cost this team their ring or that he cost Romo his ring. That is pure speculation just as much as if Bryant makes that catch in GB, they move on.
2016 was luck. Luck they missed out on Lynch and Cook. Luck that some teams were overconfident with a 3rd string rookie QB starting.
We can play the "What If" game all day with 0 conclusions including that the window has closed or that re-signing this QB to a 35M a year deal will wreck this team's chances. We don't know that.
I will speculate that if they don't re-sign him, they will start another rebuilding with a rookie QB, or FA, and might as well go total rebuild because I believe this QB gives this team it's best chance with this window that is right now wide open. I don't see any great teams in the NFC, SF, SEA, GB, MIN, NO don't scare me. Every one of them has an Achilles, just like the Cowboys do.
The situation is a simple one to me. This team has gone too far down this road to turn back or break off the path. Either they're committed and dedicated to this team, keep as many as possible and add to them, or they're not but they've just changed out, for the most part, the entire coaching staff and the OC they did keep showed enough to be kept. Coaching staffs are changes with improved results in mind and no team has more of a right to believe that than this one with Campo to Parcells to Phillips to Garrett as proof of that.
We can have these anti Prescott threads out the wazoo and it's not going to change what is going to happen, they are going to re-sign him because he's earned it. He showed up to work every day, he's worked at improving, he's a natural leader at the position where not every QB is even considered a leader, he will sacrifice himself to make plays to try and win games and he never quits, not on himself or his team. So, he's not the guy you want. So, he's got some flaws.
The supposition with threads of this type totally miss the mark because the assumption is with a different QB, this brain trust is going to get better at picking players. Paying this QB that amount of money, when it's already out that Bridgewater will probably get 30M and that's just going to be the rock bottom for a QB1, will hamstring the FO because of the money they're paying him.
The problem is that 2016 draft was their last good one. It's not about the players picked in 2016 but in 2017-19. That is the problem.