The aim of this study is to identify the typical psychological, demographic, socio-economical, educational, health, and criminological characteristics of juvenile delinquents who tend to continue in their criminal career to adulthood and therefore obstruct the possibility of successful, non-offending integration to society. Subjects of research were young male prisoners jailed in the Juvenile imprisonment house that completed the test battery. By ex-post analysis after a period of five years, the differences between offenders and non-offenders were identified. Results show significant differences in the age of prisoners, length of imprisonment, presence of violent offence (esp. robbery) in the criminal history, number of previous offences recorded, differences in factors i, h, and q1 from the Sixteen Personality Factor Questionnaire, responses within the Hand test characteristic (affection, dependence, and communication), and in several signs of the drawings in a Draw-A-Person test. The importance and influence of listed factors is discussed.