Is Jerry going to retire?
No. He will not sell the team and retire to his billion dollar yacht.
What Jones should do is a matter of what he needs or wants from his franchise. As the owner, Jones needs the franchise for more wealth and fame. As the self-appointed President, he needs the title to remain as the number one overall executive of his franchise.
The Dallas Cowboys existed before he purchased the franchise. It will continue to exist after his time has passed. In-between those two certainties is Jones'
want for being the general manager. If it was a living entity, the franchise would tell him it does not need him as its general manager. Other qualified general managers could have always replaced Jones and did a poorer job, the same job, or a better job and the franchise would have kept on kicking.
Jones is his own worst enemy by squandering yearly opportunities for success via fresh,
totally independent perspective. I have always wished the media would constantly remind him of this fact but they could not care less about getting on Jones' bad side for fear he would alienate them. So, he has zero incentive to retire the one title he does not need since his one true weakness--the weakness shared and self-respected by any narcissist--is never exploited: his own self-image.
Jones wants his general manager title. Always has. Neither his franchise nor he require him to keep it though.