Despite the promise of a well-ordered trading system and expansion of trade liberalization in the 1980s and 1990s, why is trade governance deadlocked? This puzzle is addressed by elaborating the meaning of “crisis of success” and what such a crisis looks like at the global trading order. I argue that the global trading system is revealing a “crisis of success” in that its current failure to ensure functional trade liberalization change is a result of the initial accomplishment in successfully undergoing a power shift in global trade governance especially at the WTO, marked by greater inclusion of new emerging powers. The success of the initial first phase of trade governance (1990s–2008/2012), especially in aiding an institutional power shift at the global level, created conditions for new problems, leading to a fragmented turn toward preferential trade agreements as well as trade-mediated conflictual strategies rather than sustainable peaceful change. The chapter’s dynamic historical argument delineates how early successes in global trade policies and governance led to maximalist peaceful change, followed by crisis leading to greater use of tariffs and ensuing US–China economic and trade competition. The mechanisms that underwrote the paradox of crisis despite institutional strength are elaborated.