Participant observations from the 41 Make Peace With Police (MPWP) sessions involved 70 youthful offenders committed to the Massachusetts Department of Youth Services (DYS), 35 Boston police officers, and MPWP facilitators during 1995 and 1996. Data on the 103 juvenile offenders were obtained from a 3-year study of juvenile offenders preparing to be released from DYS long-term secure facilities. Four primary cycles of subcultural youth alienation were identified that stemmed from arrests of neighborhood drug dealers, high rates of unsolved crime, police inconsistency in decision-making, and neighborhood vulnerability. These cycles were reproduced through subcultural rituals. Nonsubcultural patterns of alienation were stimulated by an absence of supportive adults, an abdication of general moral values, and offender perceptions of negative labeling by the police. Implications of the findings for reforming the role of the police vis-a-vis juvenile offenders are discussed. 21 references, 4 endnotes, and 2 tables