I advance knowledge on the cultural outlooks of inner city second‐generation Latinos, specifically their views about getting ahead. I draw on a longitudinal study of 42 young men transitioning to adulthood from two neighborhoods in Los Angeles close to 150 interviews. Researchers have suggested urban contexts negatively impact the cultural outlooks of young men. I find urban conditions do not uniformly impinge on the outlooks of Latinos, but interact with their migrant histories and social capital. Specifically, Latinos' segregation informs their beliefs in the American opportunity structure and their social support ties their faith in their ability to get ahead. Most respondents are “resolute optimists”: strong believers in the American Dream and optimistic about their chances to succeed. “Determined young men” lose faith in the American Dream but persevere, while “self‐blamers” are harsh critics not of the American opportunity structure but their personal choices and behavior. Latinos' outlooks vary and are fluid, shifting with structural conditions.