I disagree to some extent.
I think that if the Cowboys had pressed earlier, and at the time offered deals that would then have looked to outsiders like you and me as 'overpaying', they could have closed the deal then. Plenty of teams did just that, nobody's going to tell me the Cowboys couldn't or that only these players and agents were 'smart enough' to know where the market was going.
No, I'll first believe that a known cheapskate son, gifted the job by his Daddy, mishandled things and thought he could strong-arm both into taking his cheap deals. I've read enough and heard enough to support that feeling as well. Other people are free of course to believe whatever they want or feel the need to as well.
This.
It's not incumbent on the player or the agent to lap up the weak sauce you put out for them. If you're nibbling around the edges and it's not happening, that means you have to bowl them over.
When there is looming leverage advantages and benefits for the player and you want them to forego that leverage and forego that crack at the open market, you have to boldly bowl them over to buy that leverage away from them. To say the players were dead set against signing away that leverage is to say that no number exists at which they'd have signed. And that's just hilariously dumb. Of course the number exists. We just didn't want to go there.
Instead, we patiently wanted to wait, wait, wait. And it's obvious why. Jerry was betting against them. And the players pick up on that.
Jerry can jibber-jabber and say as many positive things as he wants (as a marketer or a salesman selling his product, the team and players, to his consumers). But no matter what positive things he said about how much we believe in the players, he fundamentally believed the next step in the process would be the players not playing that well and him being able to sign them cheaper once they struggled and the leverage swung in his favor.
If you could take Jerry into a room the night before the Amari trade, and show him film and stats of Amari in our offense in 2018 and 2019, guess what. He'd have burst out of the room and made the trade and immediately signed Amari to a new deal. He'd have bowled him over with an offer rich enough to buy away that crack at free agency. And it would be considerably less than it costs to sign him today.
Same deal with Dak. If you could take Jerry into a room the first day we were allowed to extend him, and you could magically show him film and stats of how the passing offense would look in 2019, he'd have burst out of that room and immediately put together an offer that bowled over Dak and bought away the leverage they knew was looming. And it would have been a considerably smaller contract than it takes to sign him today.
I'm not blaming Jerry for not magically knowing the future.
But I'm saying he could have bet on the players and offered enough to bowl them over and buy the leverage or the free agency shot away from them, if he wanted to. A number exists that would have gotten them to sign earlier, and that number is less than either of them will cost to sign today. That number was available to us if Jerry wanted to go there. But he didn't want to. He wanted them to prove it more first, because he was betting they'd fail enough to lose their leverage.
