I would like organizations that have become part of their governments would be the richest in terms of influence, resources and freedom from prosecution. Knowing your not going to die in the can and that your organization is going to continue when you are gone(outside of a coup) would be what constitutes the most powerful. Venezuela and other South American countries as well as African warlord type organizations would be my guess. If you are going to judge simply in terms of money then no one will ever know, especially when you use a blanket term like Italian mobs or Mexican cartels. These organizations are competing with themselves and with each other. So to say one is worth $50 billion a year, $100 billion a year etc is just fantasy in my mind. Just stuff that is made up to sell newspapers and books to gullible people such as us.