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This qualitative study explores the relationships high school educators form with Latino first-generation college-going students in an urban southern California county. An integrated theoretical model is proposed, drawing from resiliency and social capital literature as well as Rogers’s notion of empathic understanding. By exploring the experiences of academically successful Latino students, this research offers insight into the attitudes, behaviors, and dispositions of supportive school adults. Empathy may be a critical element of key relationships that promote school success for a historically underserved population which now comprises the majority of students in California public schools. Respondents reported that the current focus on accountability measures may constrain educators’ ability to offer needed empathy, understanding and guidance to students.