This is the area where Jerry Jones's lack of earned NFL credentials, his absence of any unique talent or ability when it comes to evaluating and acquiring talent, and his disregard for what it takes towards building a championship team is truly highlighted.
He completely disrespects the position of GM. These guys have an almost 24 hour a day commitment to building a championship team. They earned the position by excelling at every level starting with assistant scout or assistant coach or even a former player. The move up due their their consistent success. For every GM in this league there where hundreds that competed along the way at each level.
For Jed and Jethro, it's just a part time job. They're running an oil company, building stadiums, making business deals, selling tickets and conducting endless interviews to promote their product.
For NFL GM's, winning is an absolute obsession. For the Clampets, it's merely the means to a more important end....personal credit.
They have consistently signed the wrong players and released the ones that contributed to occasional great regular seasons.
Look at any season in the past 25 where the Cowboys won 12 or more games. Note the main contributing players. Remember how they are disregarded or dismissed as "easily replaceable".
It's not shocking that Jerry claims he would pay almost anything for a championship. He doesn't understand the feeling of accomplishment a person has when it took hard work, dedication and commitment to earning something. He has always hired people to perform those tedious requirements.
Jerry failed to construct a consistent winning team when he didn't sign Dak two years ago when he should have. Dak would have been far more motivated and inspired if only Jerry had done the right thing.
If your 4th round pick becomes one of your key contributors over a 3 year period while being paid next to nothing while you can build your team further, then you acknowledge this in the most meaningful way you can.
Jerry didn't have to take advantage of Dak's contract all four seasons, extending his contract before the 2019 season would have been a fair and meaningfully gesture. It would have saved so many millions of cap space.
However you can't expect an amateur GM to possess such foresight.