A university education professor invited an urban middle school principal to "give me 50 of your most academically challenged students who need additional support to be educationally successful." What followed is an ongoing lesson in how achieving educational success is a family and community affair. One community-based middle school's attempt to build family legacies and transform its surrounding geographic community through academic enrichment for students and English as a Second Language (ESL) for their parents is described. (Contains 6 figures.)