Jerry is a businessman…not a football guy and therefore runs the team like the former.
Dak will get extended because Jerry and Stephen are both too ignorant, arrogant and vain to admit they made a mistake handling his contract and/or evaluating his potential; the interim, ticket sales are robust; team merchandise is selling; Jerry makes sure the Cowboys are in the news and being talked about with outrageous statements; and they are the most valuable sports franchise in the world…THAT is what Jerry cares about, all else is lip service.