Although political argumentation is not institutionalized in a formal sense, it does have recurrent patterns and characteristics. Its constraints include the absence of time limits, the lack of a clear terminus, heterogeneous audiences, and the assumption that access is open to all. These constraints make creative strategic maneuvering both possible and necessary. Among the common types of strategic maneuvering are changing the subject, modifying the relevant audience, appealing to liberal and conservative presumptions, reframing the argument, using condensation symbols, employing the locus of the irreparable, and argumentative use of figures and tropes. It is difficult to evaluate strategic maneuvering in political argumentation, however, because the activity types dictate wide latitude for the arguers, so there are few cases of unquestionable derailment. This essay originally was published in the journal Argumentation, 22 (2008), 317–330, published by Springer. It is based on a presentation for a conference on strategic maneuvering in specific fields and contexts, held at the University of Amsterdam in the fall of 2007.