Yeah, I really don't get it. That is why is say it is self inflicted.
Could be, but without knowing the gory details, it's hard to say for sure.
As an example. I have a friend (he's the best friend of an in-law) that is filthy rich but very down to earth. He worked his ass off to get where he is. He once told me the thing he detests, is once someone knows he has money, they think "Oh, he should be fine paying more because he has so much money and it won't hurt him as much." That attitude is prevalent.
Karmanos's wealth had diminished greatly by the time he sold the Canes. Now, maybe the Checker's were getting the short end of the stick for years, so when it came time to renew again, they wanted it to be more equitable? Or maybe, the Checkers thought that since Dundon had more money and the Canes were doing better, they should take a bigger share of the cost? Or maybe Dundon tried to squeeze them? Or maybe the Checkers thought the Canes were never going to go elsewhere because the affiliation was in state so they tried to squeeze Dundon?
Point being, I don't know the details enough to say, but Dundon is at the core, a businessman and tough negotiator and that won't likely change.