We can’t understand it, because we don’t know the actual language in the contract with Entercom. It sounds like it’s an automatic extension for 5 years if WRKO matches the contract within 6 months of the expiration date. If they are only required to match his salary, Howie may indeed be screwed.
I agree: it is difficult to make a proper assessment without being able to see the terms of the contract (which, of course, we never will).
I heard some mention on another thread that what he needed in his WTTK deal was a clause allowing him to bolt on 24 hours notice from his employer. WRKO would have had to include this in their matching offer thereby allowing him to bolt.