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Douglas McGregor’s conceptualization of Theory X and Theory Y has influenced management practices for almost six decades, despite the relative paucity of empirical support. This empirical study examined the relationships between health care employees’ perceptions of (1) manager Theory Y and Theory X orientations; (2) work unit psychological safety, organizational citizenship behavior, and service quality; and (3) the employing entity. The study used survey data from more than 3500 employees of a large US health care system and analyzed them using confirmatory factor and hierarchical regression analyses. Results indicate that McGregor’s conceptualization is best considered as two separate constructs—Theory Y and Theory X—rather than as one-dimensional X/Y construct. This study’s three dependent variables were positively related to Theory Y and negatively related to Theory X, with larger Theory Y effect sizes. Psychological safety partially mediated the relationship between Theory Y and the dependent variables Y. Practical implications are presented.