Background The objective of this study was to estimate the lifetime prevalence of diversion (i.e., trading, selling, giving away or loaning) of four classes of controlled medications (pain, stimulant, anti-anxiety, and sleeping) among adolescents, and to identify demographic and behavioral characteristics of adolescents who divert their own controlled medications. Methods A web-based survey was self-administered by 2744 secondary school students from two southeastern Michigan school districts in 2009–2010. The sample consisted of 51% females, 65% Whites, 29% African-Americans, 4% Asians, 1% Hispanics and 1% from other racial categories. Results Thirty-three percent of the students had ever been prescribed at least one controlled pain, stimulant, anti-anxiety, or sleeping medication. Approximately 13.8% (n = 117) of lifetime prescribed users of controlled medications (n = 848) had ever traded, sold, given away or loaned their medications. Multiple logistic regression analyses indicated that being approached to divert medications, nonmedical use of prescription medications, externalizing behaviors, and being non-White were significantly associated with the diversion of controlled medications. Multiple logistic regression analysis indicated that the odds of substance use and abuse for lifetime prescribed users who diverted their controlled medications were significantly greater than prescribed users who never diverted. Conclusions The findings indicate that approximately one in seven prescribed users had diverted their controlled medications in their lifetimes. Being approached to divert medications and substance use are more prevalent among adolescents who diverted their controlled medications. Careful assessments, diligent prescribing and monitoring of controlled medications, and continual patient education could be useful in reducing medication diversion.