The paper considers the organizational inequality as a characteristic of a societal system and a factor of social and economic development. An ambiguous treatment on the part of states to their subjects as to availability of the organizational alternatives for them in history is discussed. A game model of the conventional expectations as a factor of sustainability of societal systems is developed. A distinction between impersonal and personal dictatorships as well as between old and adolescent dictatorships is contributed. Prerequisites for validity of these dictatorships and their consequences for the organizational and force inequalities are analyzed.