The concept of ‘gentrification’ came from observations of the urban transformations that took place in context of the economic transitions in Western, democratic, developed, and liberal economies. From the first generation theories of supply-side (rent-gap theory) versus demand-side drivers (post-baby-boom return to city by tertiary economy workers) to the more recent critiques of the consequential spatial inequities in the city, the physical manifestations and consequences of the transformations under the rubric of ‘gentrification’ as applied to non-Western illiberal economies will require more specificity. This paper will look at the case of neighborhood-scale transformation that have taken place in the western end of the former French concession in Shanghai since the mid-2000s to unpack the drivers, pathways, and actors that have imparted a vibe in the neighborhood not unlike that in Williamsburg in New York or Prenzlauer Berg in Berlin. A conceptual framework of the ‘urban loophole’ in addition to what the author is terming ‘gentrification with Chinese characteristics’—the ‘Chinese characteristics’ references Harvey’s ‘neoliberalism with Chinese characteristics’ rather than the CCP’s ‘socialism with Chinese characteristics’—will be deployed to understand both the rapid re-globalization that has taken place in the acceleration of post-socialist economic liberalization and marketization starting in the 1990s—where the rent gap is city-wide as a result of planned economics—as well as in the dual market, with the coexistence of planned and market, of the transition economy that has rendered China’s opening since the 1990s the Black Swan for political economists. The constellation of local and international actors and public-private alliances that have affected the transformations will be contextualized also against the spatial specificities of the neighborhood, produced under modern-era planning concepts and with building types, in contrast to pre-modern architectural types, that also facilitated their rapid appropriation and redevelopment.