Crises and exceptional situations are usually described as exogenous challenges for political leadership. Leaders are reactive to their political environment (structure), which strongly shapes their activity as situational and contingency theories of leadership emphasize it. In contrast, this paper claims that crises and exceptional situations might be engendered endogenously, by political agency. Drawing on Burns’ charismatic-transformational and Grint’s constructivist theories of leadership, and on Schabert’s concept of creativity, the paper provides an agency-focused interpretation of (extraordinary) political situations. Leaders give meaning to the political situation (Oakeshott); they can generate and/or shape crises for their own interests. The paper relies on Palonen’s differentiation between two types of contingency (Machiavellian and Weberian) to set up a two-dimensional framework for analyzing political situations and types of political action. The paper provides two empirical examples (George W. Bush’s leadership after 9/11 and Hungarian PM Viktor Orbán’s unorthodox crisis-management from 2010 onwards) in this framework.