Over the last five decades, immigration has profoundly transformed the population of metropolitan New York, long divided by race and class. The almost-forgotten 'underclass' debate established that New York was the nation's capital of concentrated poverty, which grew significantly worse during the 1970s and 1980s. Though more recent data show that New York has achieved a remarkable turnaround since 1990, most probably associated with immigration, it remains a city of economic extremes and stubbornly high poverty. Concern about where new immigrants—and their children—might fit into this matrix of urban inequality led several leading social scientists to hypothesise that some members of the second generation would be downwardly mobile. To investigate this possibility, in 1999 and 2000, the Immigrant Second Generation in Metropolitan New York (ISGMNY) surveyed 3,415 young people aged 18 to 32 years, from five immigrant and three native-born racial and ethnic backgrounds, about their life trajectories. This paper conducts an analysis of the contextual effects of the neighbourhoods in which respondents grew up on their later experiences in terms of educational attainment and labour market success. Using OLS and HLM modelling, we find small but consistent and theoretically interesting effects. In particular, growing up in a poor neighbourhood has a negative effect on later outcomes, while growing up in a black neighbourhood does not, once poverty is taken into account.