Data were obtained from nationally based random sample surveys of police chiefs and sheriffs. Of the participants, 1,279 were white, 77 were Hispanic, 23 were black, and 25 were Native American or Korean. Participants were police chiefs of municipal police organizations or sheriffs of county police agencies. The following variables were identified as potential stressors affecting the institutional and organizational environment of police executives: executive selection, legitimacy issues, control over hiring procedures, and organizational complexity. Individual characteristics of interest included educational attainment, belief in public service, ethnicity, and length of service. Dependent variables involved role stress, work alienation, and anomie. It was found that institutional and organizational features of the police chief's occupational environment often had a negative relationship with stress constructs. Individual characteristics had positive relationships with all stress constructs. Positive contributions of individual characteristics in many instances, however, disappeared in the face of institutional and organizational stressors. Specifically, in all associations involving role stress and in half the associations involving anomie, positive benefits gained from particular individual characteristics disappeared when contextual factors were included in the analysis. On the other hand, effects of education, minority status, experience, and belief in public service on work alienation remained significant, even in the presence of institutional and organizational stressors. Appendixes contain indexes of institutional, organizational, and stress-related variables. 32 references, 2 notes, and 4 tables