Here's the thing Waylon: college athletics is a big business. But when guys like Gene were coming up through the ranks, it really wasn't. It was a less important and undersupervised part of big universities. The fact that, today, you want successful businessmen to be your ADs doesn't mean that there still aren't some "old school" guys around who really grew up as glorified coaches. (Not that there is anything wrong with being a coach -- just that those skills are very different from those that you would want an AD to have).
My poing being you should not assume Flipper is going to speak and act like a lawyer/MBA just because today, decades after he broke into the business, that is the type of person you'd want to hold his job.