Why do bad deals happen to good artists?

Reading about horrendous deals involving renowned artists in their early days, it is tempting to wonder whether those mistakes were just that. In other words, with the benefit of hindsight (or better management) the bad deals could have been avoided. Or perhaps, those ‘mistakes’, as awful as they look out of context, were almost necessary to get an entertainment career to the next level, because they might have led to propitious connections and great professional developments.