The New York metropolitan area is one of the oldest, largest, and perhaps most complex urban region in the United States (U.S.). Its 23.7 million residents live across four states, produce a GDP of more than $1.7 trillion, are governed by a fragmented political system, and experience persistently high degrees of geographic and racial/ethnic inequality and segregation. This chapter investigates the evolving spatial organization of occupation and race across the metropolitan area. While white professionals have traditionally lived in an outer ring of suburbs and blue-collar immigrant and minority groups have lived closer to the city center, our research shows that the forces of gentrification and minority and immigrant suburbanization have been turning the metropolitan area inside out. Specifically, young, usually white, professionals are increasingly located in and around the central city whereas many working-class minorities have shifted away from it. At the heart of this spatial reordering lie the diminishing plurality of native-born whites within the region and the increasing share of immigrant minority groups, especially for foreign-born Hispanics and Asians. This trend has lessened the share of white males in better occupations even as the region’s occupational structure slowly but inexorably tilts toward managerial and professional occupations. Technology is transforming white-collar work as blue-collar work continues to disappear. Dramatic shifts are thus afoot, yet inequality and segregation remain high. We argue that these changes in the spatial organization of the metropolitan area challenge us to see these inequalities from a new vantage point. As elites are now more likely to live among less advantaged groups, this may provide the social basis for new thinking.