That's on Jerry for two reasons.
1. Jerry procrastinated on getting Dak signed. It should have happened two years prior. Jerry, knowing that Dak was his starter for the next several seasons, should have been proactive in signing Dak after his 3rd season. Had he done so, the contract would have been greatly reduced.
2. Jerry did not have an alternative choice for his starting quarterback. He had no other potential QB on the team that could have been the Cowboys future starting QB. The Cowboys have never been active in drafting quarterbacks in order to create a competitive environment.
if the Cowboys were to draft as QB in one of the top three rounds every three years then they would always have an up and coming QB capable of starting. Not only would this make the position competitive but it would offer the Cowboys a powerful negotiation tool as well as valuable trade value.