We focus on a key IR Theory article by Alexander Wendt (1992) and two Jackson Pollock paintings. Our aim is to identify meanings Pollock’s art communicates and reveals for Wendt (1992). It derives from an appeal to visual imagination and a desire for semiotic interpretation of Constructivist view of anarchy. The visual sign is an association such that there is Wendt’s theoretical claim on the one hand and an abstract painting on the other. We do not gaze at Wendt’s claim, we read it. We do not read a painting, look at it. This remark does not imply a one-way relationship. We can argue that a specific painting comes to life in our mind where colored movements are inextricably mixed up when we read the constructivist claim. Both Pollock paintings selected for our sign-making effort confirm the dynamic character of Constructivism and reveal not only three but countlessly many anarchies in international relations. They foment our assessments of abrupt changes of intersubjectivity among states. Cyclicality of dripped paints provides an anchor to fix Wendt’s anarchy conceptualization in these structural-abstract paintings. As to Wendt’s concept of anarchy, it acts as a helper, as a standard, against which interpretations of Pollock’s artwork construct meanings.