Ashley apparently had NO IDEA they were still paying off transfer fees for some of the players at the club, and didn't realise that when a club agrees a fee of x million for a player, the cash doesn't change hands overnight but is usually fixed over a certain period - this apparently came as something of a shock to him after he'd bought the club, and was a financial burden he simply had not factored in.
Seems there were a few things not in the brochure. A victim of his own ego and naivity.
Surely due diligence would show things like this up though - or did he not bother with that?