The main focus this research is to analyse the organizational interlinkages between the International Monetary Fund and the World Bank since their inception. While there are striking similarities between the Bretton Woods ‘twins'', as they are usually referred to, such as in their organizational structure and complementary lending policies, in recent times significant differences can be noticed in their functioning style and extended jurisdictions. The research discusses the ontological beginnings of the Bretton Woods Institutions. It elaborates the ideological philosophy of the two organizations as also reflected in their lending policies. It also traces the changing roles and functions of the two institutions separately over a period of five decades. Areas of convergence and divergence between the BWIs with respect to their organizational set-up, leadership roles and lending policies are examined in detail. The research discusses possible ways of reforming the Fund and the Bank in the context of increasing debates about democratization of the international organizations. It highlights different approaches of reforms and discusses their viability.