The purpose of this instrumental case study was to understand the ways in which the leaders of one high-achieving, large, urban high school communicate with Latino families about math with the intent to shine a light on the issue of communication with families as it relates to student achievement and the persistent math achievement gap among Latinos. Specifically, the researcher set out to answer the following four research questions: (1) How do the leaders of one high-achieving, large, urban high school communicate with Latino families about math? (2) Is communication with families about math purposeful? (3) Is there consistency in message? (4) Is there a shared belief in the role that communication with families about math plays in student math achievement? This study was a qualitative analysis involving the triangulation of interviews, documents, and audiovisuals. The findings show that while the leaders of this particular school do share beliefs and they do communicate consistently with students, they do not communicate as consistently with families, nor do they communicate consistently or purposefully with Latino families specifically about math. Despite these findings, however, the school boasts high achievement in math among Latinos, which, the researcher holds, is likely due to other factors, including the strong sense of community, the pervasive positivity, and the many systems of support; this would have to be confirmed through future studies. This study provides fertile ground for future studies, as it brings to the fore notions of purposeful communication with families; purposeful communication with subgroups; purposeful communication specifically about math, community, and positivity; and the effects of systems rather than aspects of systems on student achievement. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]