Obviously I can't be sure since Jerry doesn't tell me anything, but circumstantial evidence suggests that's the plan. The details of his contract suggest that. Restructure before 2022. Restructure again before 2023. Then extension before 2024. One leads to the other. If they don't do this, then that means the Cowboys would be eating a tremendous cap hit one of those years. Restructure and the extension avoid that.
If he and the team put together strong seasons with some playoff success, maybe.
If you assume no deep playoff run or championship in the next two seasons, I don't see how any organization could justify an extension for an 8 year QB with no tangible success.
It is hard to imagine improving the team around him significantly the next two seasons given the cap constraints, so I think his best window has closed.
I think it's much more likely that the QB plays himself out of town and\or out of a starting job than to be extended here.