Harry Bosch, totally agree. Or at least, I'm definitely on board with your view on things.
Should at least be doing our best to convince him that with a respectable manager like Shez and a few top top players like himself.. next season could be a whole lot better.
Im currently in a similar position with the team I coach... my best player is thinking of leaving but not 100% sure, I'm telling him that with the additions we are going to make, and the weaker players we are moving on - that next season we could potentially win the league. (Okay, not overly the same - because don't think Latics have the chance to win the league, but definitely play offs with signings like Ripley)
I've not once just said "you know what, ye the team you're thinking of leaving too are great, we're awful - go ahead and leave"