This article conducts a comparative analysis of Iran and Turkey, two neighboring countries in the Middle East that share Islamic cultural identities and a clear political interest in promoting regional détente. While Turkey has made great strides in terms of consolidation of its ruling elite, industrial growth, job creating investment, the expansion of civil society, capacity building (economic development, and improving health care and education), and housing sector, Iran has had comparable successes in some areas, such as capacity building, but certainly has fallen behind in other areas, such as losing managerial skills, brain drain, widening divisions within its power structure, and growing restrictions on the expansion of civil society and democratic freedoms. One notable difference between the two countries is that trust in public institutions is higher in Turkey than Iran. Whereas Turkish civilian leaders exhibit noticeable disinterest in military rule, Iran’s clerical establishment has forged an alliance with the Revolutionary Guards. These issues are discussed with particular regard to the problems confronted in both countries in tackling domestic and foreign policy matters. The article highlights why the normalization of relations with the United States more specifically and the Western world more generally would benefit Iran. The political and economic troubles that Iran faces are likely to undermine Iranians’ support for the regime in coming years.