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This series of hypothetical cases, written for executive training programs for new mayors, frame the quintessential problems faced by municipal chief executives. These include labor relations and negotiations with a public employees union, the question of the degree to which political influence should be extended to influence the tactics and mission of a city agency staffed by people who view themselves as professionals, and the trade-offs and strategic options that arise when a chief executive must cut back a budget. These cases explore the mandates and limits of political power through tightly focused decision-forcing narratives.