He always waits and waits to 'tough negotiate' in hopes the clubs will cave on the price and it'll go down. What he risks, and what usually winds up happening, is that the clubs either don't sell, or sell to someone who makes a realistic offer. In the end, when the transfer window is about to shut, we either wind up over-paying (15m for Matri) or picking up a charity-case (Toni, Borriello.... Pazzini??)