Ensuring student academic achievement is a constant challenge for public school educators. A review of the relevant literature revealed considerable research pertaining to specific leadership behaviors and leadership styles that impact academic achievement; it clearly demonstrates that principal leadership matters. The literature also suggested that principals’ leadership behaviors affect school organizational health and these features influence academic achievement and perhaps more so for at-risk student populations. What appears to be less understood is the nature of academic achievement among students identified as “at-risk.” Organizational health provided a conceptual framework within which the relationships among principal and teacher behaviors and at-risk student achievement could be investigated. Therefore, the purpose of this causal-comparative study was to compare identified high poverty schools that are “high performing” and those that are “low performing” to investigate differences in the organizational health. The study also investigated other school level teacher variables to further understand the relationship between such characteristics and academic achievement of at-risk students. The 37-item Organizational Health Inventory for Elementary Schools (OHI-E, Hoy, Tarter, & Kottkamp, 1991) was administered online to teachers employed in selected high performing and low performing high poverty schools located in seven public school districts in southeastern Louisiana. The results of the study indicated significant differences between the two groups in terms of their organizational health as well as collegial leadership, resource influence, teacher affiliation, and academic emphasis. No significant differences were found regarding institutional integrity. Implications related to strong effective leadership, organizational change, and maintaining healthy organizations are discussed.