Cosmopolitan, often English-speaking, and typically conversant in the language of civil society and democracy, the heirs apparent in many of the countries of the Arab world--republics and monarchies alike--are caught between their lip service (and perhaps genuine attachment) to the liberal political values of their elite education and their reliance on the patronage machines constructed by their fathers in an era that prized socialism, nationalism and state-building. Under what circumstances can individuals whose access to power is a reflection of their familial or personal connections be relied on to create the genuinely representative institutions they seem to advocatet Drawing on cases from across the region, as well as insitances of pivotal figures outside the region, like Spain's King Juan Carlos, but looking particularly at the tensions that attend Saif al-Islam al-Qaddafi's ambivalent pursuit of authority and responsibility in Libya, this paper examines the prospects for political succession in a region characterized by aging leaders and uncertain institutions.