My father-in-law played with both at Arkansas. Couldn't stand Jerry (says he was an a-hole), loves Jimmy (to be fair, Jimmy got him back and forth from SETX to Fayetteville since he had a car and my F-I-L didn't). I think for some of us older Cowboy fans, Jerry rubbed us the wrong way in the beginning. But he has been a great marketer and a dedicated owner. He has been an average GM at best, much like the late, great George Steinbrenner when he was trying to get out of his lane.
But as an owner, like Steinbrenner, he absolutely deserves to be in the Hall. Greatest owner of all time? I would say the name Art Rooney comes to mind...