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Despite the crucial role they play within the criminal justice system, community corrections practitioners are largely understudied. The events and factors that influence staff views and practices remain unknown—particularly the role of the political environment. Using in-depth interviews of 25 probation and parole frontline and management staff within one agency, we use a novel life course method (Nelson 2010) to map their career trajectories. We use thematic analysis techniques to uncover and understand how shifts in state and local politics across a career influence attitudes toward punishment and practice, and impact morale. Findings suggest women’s perspectives vary by individual characteristics, but similarities about attitudes exist within geographic regions suggesting localized political issues may also bear influence. The results of this study can inform upper management regarding best implementation practices for policy and procedure to improve organizational climate and boost staff morale.