The Chronic Self-Destructiveness Scale (CSDS) was administered to 80 putativcly non-delinquent male high school students and to 101 delinquent males, revealing high internal consistency reliability for both groups. CSDS responses were factor analyzed independently, and separate three-dimensional oblique structures were found for each group. A major factor underlying the self-destructiveness of both groups involves alcohol use and other related risky behavior. For the high school males, two factors which distinguish between Active Responsibility and Passive Avoidance of duties also underlie their CSDS responses. The structure underlying self-destructiveness in delinquent males does not distinguish between active and passive forms of irresponsible behavior. An independent, ‘acting-out’ factor, which did not emerge for the normative sample, was interpreted for the delinquents. Interestingly, just as male delinquents may not distinguish between active and passive forms of neglecting responsibilities, their high school counterparts may not distinguish between active and passive engagement in risky behavior. Juvenile delinquency intervention strategies are suggested. © 1998 by The Haworth Press, Inc. All rights reserved.