Ahhh, let's cut to the chase. Howie didn't understand his own contract and the boy genius from Chapel Hill was in such a rush to rub it in Entercom's face that he opened his big mouth and screwed himself. All he had to do was STFU for a couple of months and he was home free. End of story.
I don't think *anybody* understood the implications of the contract, as it was new law, and broadcasters in Mass were spouting the "non-competes are illegal" thingy everywhere. There was no way to know how ONE judge would find and settle the issue.
At the time there were questions of whether artist contracts in an of themselves were illegal...as they were "covenants not to compete". And it was not unreasonable to think that due to the new law, Entercom could not keep him
after his contract was over...no matter what.
It's one thing to read a contract....it's another thing to interpret it in light of new labor laws that were enacted after the contract was written.
Again, it came down to one judges opinion/finding...and there was no precedent.
End of story.
Some people like Howie, some don't.
This has nothing to do with your personal feelings.
He had a choice....(1) take a serious (I mean serious) pay cut from Entercom. (2) branch out on his own where he had the possibility of making more than Entercom was offering...and he would be in control of his career and his future.
It's a no-brainer that he would attempt choice #2 at this point in his career.
And it gives him much more flexibility going into his pe-retirement years. Doing the show from home (Entercom fforbid). Doing it from Florida (Entercom forbid), picking his own guest hosts (Entercom chose them previously) production elements, promotion, etc. And he controls the syndication effort (Entercom held it previously). If he loses an affiliate he can pick up another. (Like having a diversified portfolio).
My guess is that his agent/attorney will make some gentle overtures to WRKO over the next couple of years...and that Howie's program will end up on WRKO. It will be a win-win for both of them.