Attention-deficit/hyperactivity disorder (ADHD) is among the most common mental health disorders of childhood, occurring in 3% to 5% of the population and more often diagnosed among boys than among girls (for review, see Barkley, 1998). Children with ADHD are characterized by developmentally inappropriate levels of inattentiveness and/or impulsivity and hyperactivity that cause significant impairment in behavioral, academic, and social functioning. These difficulties begin early in life, with kindergarten or first-grade teachers often alerting parents to problems in the classroom, thereby triggering an evaluation. The disorder is now known to persist well beyond the elementary school-age years, with the majority (about two thirds) of children continuing to exhibit problems into their adolescent (Bagwell, Molina, Pelham, & Hoza, 2001; Gittelman, Mannuzza, Shenker, & Bonagura, 1985) and adulthood years (Barkley, Fischer, Smallish, & Fletcher, 2002; Mannuzza, Klein, Bessier, Malloy, & LaPadula, 1993). For a number of reasons, children with ADHD have become a target of research inquiry among substance abuse researchers (Flory & Lynam, 2003; Lynskey & Hall, 2001; Smith, Molina, & Pelham, 2002). Although there are some inconsistencies across study reports, with some studies reporting group differences in substance disorder (Gittelman et al., 1985) and others not (Biederman et al., 1997), the most recent report on this topic (Molina & Pelham, 2003) comes from our program of longitudinal research on ADHD conducted at the University of Pittsburgh Medical Center ADD (Attention Deficit Disorder) Program. In Molina and Pelham (2003), 142 children diagnosed with ADHD at the ADD Program (per the Diagnostic and Statistical Manual of Mental Disorders, third edition, revised [DSM–III–R], or fourth edition [DSM–IV]) were reinterviewed as adolescents. Detailed assessments of their substance use (age of initial use, frequency, quantity, etc.) and abuse/dependence were collected for comparison to use and abuse in a newly recruited sample of 100 adolescents from the community who were demographically similar to the probands. In an effort to address previous inconsistencies in the literature, the assessment included a broader range of substance use behaviors than had been reported in previous studies. We found that, compared to adolescents without childhood ADHD, probands were more likely to have been drunk in the previous 6 months, to have used an illicit drug or marijuana, and to have had alcohol-related problems (e.g., fight with parents over drinking alcohol). Of particular relevance to the current study were the findings regarding cigarette use by the probands. As adolescents, the children with ADHD were three times more likely than the comparison adolescents to report daily cigarette smoking, and probands reported first smoking cigarettes and becoming daily smokers at significantly younger ages than did adolescents without childhood ADHD. Among probands, severity of childhood inattention symptoms and persistence of ADHD were associated with quantity and frequency of cigarette use in adolescence, even after controlling for childhood oppositional defiant disorder (ODD) symptoms, childhood conduct disorder (CD) symptoms, and adolescent CD. This finding indicated a unique risk for nicotine addiction attributable to ADHD and its persistence over and above a tendency toward problem behavior in general (which is also a known risk factor for cigarette use). Our findings of elevated risk for regular cigarette use among children with ADHD are not without precedent. Milberger and colleagues reported a statistically significant elevation in daily cigarette smoking by adolescence among clinic-referred children with ADHD compared to children without ADHD (19% vs. 10%, respectively; Milberger, Biederman, Faraone, Chen, & Jones, 1997). More days of tobacco use by the ages of 13 to 15 was predicted by childhood ADHD, but not by childhood CD without ADHD, in another clinic sample followed longitudinally (Burke, Loeber, & Lahey, 2001). Finally, in a sample of middle school students, ADHD based on symptom ratings by teachers was concurrently associated with student self-report of cigarette and smoke-less tobacco use (Molina, Smith, & Pelham, 1999). All of these studies indicated contributions of ADHD diagnosis or symptomatology to risk for tobacco use above and beyond associations with antisocial behavior (i.e., CD diagnosis, delinquency score). Taken together, these findings are important given the high prevalence of ADHD in children and the well-established difficulty of quitting smoking once habitual use is initiated. Indeed, most daily adult smokers begin their smoking careers in adolescence, illustrating the potential public health importance of preventing nicotine addiction among youth (U.S. Department of Health and Human Services, 1994). In the Molina and Pelham study (2003), adolescents who reported daily smoking also reported having done so for an average of 2 years. Thus, childhood ADHD appears to set the stage for early exposure to cigarette smoking, habitual use, and perhaps intractable addiction (although the latter supposition remains to be tested empirically). The data also indicate that not all children with ADHD develop cigarette-smoking habits, which creates an opportunity for researchers to examine characteristics of children with ADHD that decrease or increase risk for cigarette smoking uptake in adolescence. The study of coping skills forms an area of substance use research in which findings have generated significant implications for intervention and in which there is heuristic appeal for research on adolescent ADHD. Stress and coping models of adolescent substance use have much empirical support in general adolescent populations (for reviews, see Wills & Cleary, 1995; Wills & Hirky, 1996). Certain types of coping skills are particularly important for reducing the adverse impact of life stress and are generally associated with decreased vulnerability for substance use that includes tobacco. One active coping strategy, behavioral coping (e.g., doing something to solve the problem), has repeatedly been found to be inversely related to adolescent smoking cross-sectionally (Pederson, Koval, & O’Connor, 1997) and longitudinally (Wills, 1986; Wills, Sandy, Yaeger, Cleary, & Shinar, 2001). Cognitive coping (e.g., trying to see the problem in a different light) is also associated with decreased vulnerability to smoking, although findings have been less robust (Wills, 1986; Wills, Sandy, et al., 2001). Use of less effective coping strategies associated with increased risk for smoking among adolescents include anger coping, hangout coping, helplessness (giving up), and distraction or avoidance (Pederson et al., 1997; Sussman et al., 1993; Wills, 1986; Wills, Sandy, et al., 2001). Social support from parents, discussed by Wills (1986) as an additional strategy for coping with problems, has also enjoyed widespread empirical support as a protective factor for adolescent smoking (e.g., Chassin, Presson, Sherman, & Edwards, 1992; Fleming, Kim, Harachi, & Catalano, 2002.) For several reasons, the elevated risk for cigarette smoking among children with ADHD that we and others have found might be partly explained by coping skill deficiencies in this population, especially among children with persistent ADHD. Such a hypothesis is supported by correlations found in the general adolescent population between coping skills and temperament dimensions onto which the core symptoms and associated features of ADHD can be directly mapped. These results are best illustrated in the research findings of Wills and colleagues (Wills, Windle, & Cleary, 1998), who report significant associations between temperament and self-control dimensions that include activity level (e.g., never seem to stop moving), task attentional orientation (e.g., once involved, can’t distract), and impulsivity with coping skills such as behavioral coping and anger coping. Indeed, it is widely recognized that adolescents with ADHD have large skill deficits and poor coping strategies in a variety of academic and interpersonal settings (Robin, 1998). Thus, one reason that children with ADHD might have elevated risk for regular cigarette smoking is a maladaptive style of coping with the academic, behavioral, and social impairments common to children with ADHD. As such, we hypothesized that adolescents with a childhood history of ADHD would have fewer adaptive (i.e., behavioral and cognitive) and more maladaptive (i.e., avoidant) coping skills than would adolescents without a childhood history of ADHD and that this deficiency would mediate the association between childhood ADHD and later cigarette use. To this end, the current study tested this mediational model for adolescents as an extension of the findings reported by Molina and Pelham (2003).