This chapter compares the foreign policy decision-making style and diplomatic priorities of Éamon de Valera and Franklin D. Roosevelt during the period 1932 to 1939. Before coming to presidential office, both men also saw value in promoting national interest through international engagement albeit within limits. Both men had to repay many political favours when it came to forming cabinets and administrations and in turn the existing diplomatic culture. Decisions about appointing an amateur or professional were influenced by a myriad of factors. Who were the men and women interested in the Dublin and Washington posts respectively? The chapter argues that the appointment revealed much about Roosevelt and de Valera’s interest in the other country and that the quality of the appointee would only emerge when they had to establish political and personal networks to assist in the promotion of national interests and when dealing with daily events