Leaving Citadel -- whether on his own terms or the company's -- makes sense. The idea of "Regional" managers has always sounded like an unneeded layer of management for any radio company.
Seriously, in a fully-staffed cluster, you have a local sales manager, a national sales manager, a general sales manager. Then there's the GM. Then there's a regional VP (or in Citadel's case, Regional Prez) before you get into the people who actually work at corporate HQ.
There's almost as much red tape in radio as there is in government. Seriously, what really IS the point of a regional VP when each market already has a GM overseeing one or two levels of middle management?