Give him a few years of not working a real job, and then ask him what he wants. Some people will say they are happy, others will start looking for that real job.
Ask Monty. At some future point, Monty will be getting some feelers to leave and I'd have to think a boss like SL would be a reason to stay because of the respect PM has for a guy who's in the PFBHOF. I also think he'd be an infrastructure builder who could raise money immediately not just from the usual TU fans/donors, but from the entire business community in the region. Also a proud native Oklahoman. Most people couldn't tell you who the AD is at any school, but virtually everyone would immediately know ours.