This paper explores why anti-left sentiments have recently emerged in some Asian cities and, in particular, why urban middle classes have frequently, if not persistently, protested against the socioeconomic reforms of new left governments. The global middle-class thesis ascribes the emergence of anti-left sentiments to the liberal-democratic ideology and conservative values of the affluent middle classes. However, this paper does not characterize these anti-left sentiments as ideological or value-driven conflicts. Alternatively, this paper argues that this phenomenon has stemmed from the immediate reactions, or hysteresis, of the middle classes to the critical instability that the new left governments have caused in their taken-for-granted lifestyles in unique urban spaces. To corroborate the argument, this paper compares the cases of the most contentious middle classes in three East and Southeast Asian countries, including Japan’s wage earners or salarymen, South Korea’s self-employed, and Thailand’s urban professionals.