The prevailing situation in which students of color represent over one-third of school enrollments, yet teachers of color represent merely one-tenth of the nation's teacher force, is an important yet rarely considered factor amidst the constant claims of teacher shortages. Urban and rural schools struggle with an inadequate supply of teachers, but shortages are more concentrated in selected fields such as bilingual education and special education. In urban school districts that are majority children and youth of color, students have great need for teachers who can be cultural intermediaries to navigate between school and home cultures. In this article, the authors describe their programmatic efforts to address the urgent shortage of certified Latino bilingual teachers for the Chicago Public Schools. They start by setting the Chicago context and introducing the "Pathways" opportunity, portray their Project 29 Pathways program in some detail, and close by discussing outcomes and lessons learned.