This case explores the challenges and opportunities facing Bill Evans, the president of the West Kentucky Media Division of Paxton Media Group. As the leader of several local new outlets in Kentucky and Illinois, he must develop strategies to preserve the businesses within his portfolio in the face of longstanding declines within the media industry. The case reveals the actions that Evans took to reduce costs and boost efficiencies within his organization, such as consolidating office locations, using generative AI to produce headlines and rewrite press releases, and adapting his workforce to publish stories across multiple platforms. It also explores the communication strategies that Evans used as he implemented these organizational changes. The case is suitable for use in MBA and executive education courses on media, communications, and leadership.