The problem with "simply" waiting out his existing contract before he signs a new one is that the moment his old contract expires, he loses a ton of leverage with any new employer. Any other station can suddenly say "Hey Howie, we said we thought you were worth $5mil. Guess what? We think you're worth $50k. Take it or leave it." And he'll have to take it because the alternative is no airshift at all. And if he's off the air for more than a few weeks, he'll rapidly start losing audience, permanently.
I, too, would say he's like Manny Ramirez, because he must be on drugs to think he's gonna get even a fraction of what he got last time in his next contract. If he gets one at all. WTKK, I'm told, has minimal interest. Where else is Howie gonna go? Clear Channel? Maybe, but I seriously doubt they'll give him much cash to do it, and he'll still be on an inferior AM signal. (unless 101.7 becomes a simulcast of 1200, which is not a sure thing)