The aim of this paper is to contribute to the ongoing debate about “Chinese assertiveness”. The paper dissects the central articles on the topic and evaluates their conceptual and theoretical insights. It ascertains that the concept of assertiveness is poorly substantiated; that proponents of “Chinese assertiveness” largely claim that it derives from structural factors that produced effects in Chinese foreign policy behavior prior to the US pivot to Asia; and ultimately, that critical accounts, since they reject the very concept, lack theories that can explain Chinese assertiveness. This article attempts to address these shortcomings. First, the article reconceptualizes assertiveness and connects it to grand strategy change. Second, this change is reactive and occurs after, not prior to the US pivot. Third, in order to provide greater theoretical adequacy, this article combines material factors with institutional factors and show how they dialectically interact with status aspiration, as part of the struggle for the positional good of leadership. To show the conceptual and theoretical plausibility of the argument, the paper outlines the dialectical interplay between positional barriers in the ADB and the US pivot to Asia, on the one hand, and reactive Chinese assertiveness and the AIIB, on the other.