This report considers the relationship between ethnicity and poverty through case studies of inner city men. In particular, the spatial mismatch hypothesis and the “dual” or “segmented” labor market theory are put to the test of accounting for empirical findings on the employment dynamics among a sample of inner-city men representing four distinct ethnic/racial groups. Data are drawn from a major survey conducted in Chicago by the Urban Poverty and Family Structure (UPFS) project. The UPFS survey began in 1986 and was completed in 1987. It consisted of a stratified, probability sample of persons between the ages of 18 and 44 years, mostly parents, within the city's official poverty areas as defined by the U.S. Census Bureau. The sample was stratified by four major social categories, persons of black or white heritage, and Mexican and Puerto Rican origin Hispanics. An additional component of this project, an employer survey, also provides findings with relevance to the work here and is subsequently cited. Though each of these perspectives appears to derive at least some support from the findings, neither can fully account for the patterns of the data. The results of this work ultimately raise as many questions as they answer; a number of important shortcomings of the contemporary perspectives on poverty are suggested as well as a number of clear directions for further research.