Teachers' work is inherently political at both the interpersonal and structural levels. Yet, now, many teachers are under state-sanctioned and local pressure to be apolitical. Moreover, many teachers are citing feelings of political attack as a significant driver in their decisions to stay or leave the teaching profession, even as the US faces growing teacher shortages. Historically, the impact of teacher shortages fall most negatively upon urban intensive schools which already find themselves at the center of harsh political critique and relative political disadvantage. However, little appears in the current body of academic scholarship around teachers' political development. Against this backdrop, I conducted interviews with 15 current unionized TK-12 teachers serving in a financially imperiled urban school district to better understand urban intensive teachers' own conceptions of the political dimensions of their profession in terms of both constraints and opportunities. Of particular interest was discerning if and/or how the teachers' varying degrees of involvement in their teachers union impacts their expression of "teacher political fluency" or the skills and knowledge teachers employ to navigate the political lay of their work. The results of this five-month qualitative study offer valuable preliminary insights into the political dimensions affecting urban intensive teachers' work, teachers' strategies for navigating work-related political challenges, and how these relate to teachers' involvement in teacher unionism. Further research is recommended to build our understanding on the topic of teacher political fluency development with implications for a variety of education stakeholders including educational researchers, teacher education programs, teachers unions, and educational policymakers. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]