From a cutthroat business perspective? The smartest thing the Cowboys could have done would have been to tag and trade Prescott and sign Brady for that two year $50 million contract. You would then have two years or more to find and develop that young quarterback and have them learn under the GOAT.
And this is coming from someone who is a fan of Prescott's work.
It was definitely a missed opportunity, but the Joneses get attached to their players and don't even consider such things.
Maybe they did consider such things, but making them happen is a different thing.
They couldn't trade Prescott until he actually signed his franchise tag. Would Dak have signed sooner knowing he was going to get traded?
Were they going to find another team that was willing to give up draft picks and fork over a lot of money to Dak? I can see lots of teams investing a lot of draft capital to get a young, cheap QB. I can see lots of teams spending a lot of money on a big contract for a QB. I really don't see many teams being interested in giving up both draft picks and boatloads of money for a QB.
Could they have found a QB this off season to groom behind Brady of 2 years? I doubt Brady would have stayed in Dallas or currently in Tampa for more than 2 years.
I don't think criticizing them for not doing the smartest thing is fair as I don't think those moves were realistic. They couldn't have all happened.