This dissertation was an exploratory study of the perspectives of teachers who were knowledgeable about the effort to unionize one charter management organization (CMO) within the larger Chicago metropolitan area. Current trends in charter schools indicate high turnover amongst teachers, with contributing factors including workload (longer school days and school years), as well as a fast-paced culture of high expectations within the schools. An increasing number of charter schools nationally have unions. Organizing efforts have occurred in major U.S. cities, such as Chicago, Philadelphia, and Sacramento (Loewus, 2017). The primary source of data for this study were interviews conducted with six teachers who had been teaching for more than seven years and were knowledgeable about, and active in, the effort to organize teachers within a three-school charter management organization (CMO). All of the teachers had spent the majority of their careers in primarily Black, majority low-income schools. The interviews were conducted in Summer 2017, at the close of the academic year following a vote for union representation (2014-2015). Secondary sources of data included state collected school performance data and the documents related to collective bargaining were examined. The findings of this study reveal similarities in teachers' views with respect to reasons for unionization. The results were discussed in light of previous research and implications for practice, including a focus on the tension between structure and flexibility.