U.S. President Barack Obama’s rhetoric lends itself well as a highly interesting case study for exploring the possibilities of contemporary political rhetoric of being both successful on the one hand and rational, according to normative standards of argumentative discourse, on the other. Taking up the concept of “strategic maneuvering” as developed within Pragma-Dialectics (cf. van Eemeren 2010), a corpus of Obama’s speeches and books is analyzed in order to assess both its rationality and efficiency. The analysis shows that Obama not only knows extremely well how to use the classical inventory of (political) rhetoric, but also tries to overcome the standard strategic maneuvering of political rhetoric which is often polarizing and destructive. Obama tries to change this traditional style of political rhetoric by his orientation towards consensus and universal values and by his willingness to practice self-criticism. The evaluation of Obama’s political rhetoric has also shown, however, that Obama is sometimes forced to abandon his high ethical and rhetorical standards in order not to lose a substantial section of the U.S. voters. In some of these cases, it might be argued that his strategic maneuvering “derails”. All in all, however, Obama has shown us that a leading contemporary politician can overcome traditional party rhetoric by following new types of strategic maneuvering which, at least sometimes, successfully reconcile normative standards of rational discussion with rhetorical principles of efficient persuasion.