That is probably what he wants, after feeling he was fucked over by Levy last time! Harry is now in total control of the situation.
And not a single one of us knows what he want's to do!!
I think it comes down to how big a grudge he has towards Levy! If he wants revenge, he will leave, and probably for free to!
If it's not about getting back at Levy, i wouldn't rule out Harry signing a new contract AFTER this season! But he's got Levy by the balls now, and i think he wants him to sweat!
There's only 3 scenarios left now, and Levy loses in 2 of them!
1. We sell Harry = Levy loses and get's hate.
2. We let Harry run down his contract and leaves for free = Levy loses and get's hate
3. We gamble, Harry runs down his contract, and signs a new one = Levy wins, and get's less hate