I think he is a blow hard but I do not believe he pays radio stations. If he is not getting the ratings he wouldn't be on. Like him or not... he is on all the big markets and his show does well.
No, he does, thats his business model (or was)
He pays lots of small time radio stations, and gives them free content (about 3 hours, or one less shift they have to pay their staff for). Then with his now vast audience of many regional markets he has one large market, so he gets national advertisers, and pockets the difference as a middle man. This works so well because small regional markets often don't have enough advertisers to fill all their space, so they have airtime which is either dead or unprofitable.
Im not dissing it mind you. Its a great model if you can pull it off.
It still has nothing to do with him as a person. Making money is something drug dealers and pimps can do as easily as philanthropists (maybe easier), it says nothing about your worth as a human being either way.