Clusters of youth suicide and death are tragic for communities and present long-term consequences for the surviving youths. Despite an awareness of community-based patterns in youth suicide, our understanding of the social and community factors behind these events remains poor. While links between poverty and suicide have been well documented, wealthy communities are rarely targeted in suicide research. In response to this gap, we conducted ethnographic research in a wealthy U.S. town that, over a recent 10-year period, witnessed at least four youth suicides and seven more youth accidental deaths. Our interviews (n = 30) explored community values and stressors, interpersonal relationships, and high school experiences on participant perceptions of community deaths. Youth participants characterize their affluent community as having (1) perfectionist standards; (2) permissive and sometimes absent parents; (3) socially competitive and superficial relationships; and (4) a “bubble” that is protective but also exclusionary. Our qualitative findings reveal network influence in teen suicides and accidental deaths in a wealthy community. Greater attention paid to the negative effects of subcultural values and stressors in affluent communities is warranted. Further, our work promotes the value of ethnographic, community-based methodologies for suicidology and treatment.