This chapter takes a fresh look at both sides of the complex interrelationship between territorial politics and political careers. In a first step, the territorial dimension of political careers is mapped out. In contrast to the rather simplistic unidirectional career ladder model, current opportunity structures for professional politicians endorse multiple movements within and across various territorial levels of government. Recent empirical career studies thus reveal a multitude of regional and national career patterns. In a second step, the career perspective is introduced into the study of territorial politics. Individual political careers and collective career patterns can influence and condition the conduct of institutional and territorial politics via experience, anticipation and coordination. Regionally weighted opportunity structures facilitate the emergence of a regional political class, which can develop the capacity to influence these very structures according to its own collective self-interest. The chapter shows how much theoretical effort is still needed to advance analytical frameworks and conceptual tools that adequately delineate the complex interrelations between careers and territory.