Most studies on grit examined participants who were more successful than others and found grit was a significant factor. There was a gap in the literature for participants with extreme failure, first-time-detained juvenile delinquents, and the impact of grit. The purpose of the present study was an explanatory and exploratory study of grit and the interaction with other factors for first-time-detained juvenile delinquents. A sample of juvenile delinquents incarcerated for the first time in the United States was used. The results, using analyses of variances and correlational analysis, suggested grit in juvenile delinquents incarcerated correlated negatively with a mental illness screener and positively with higher social self-esteem. Examining grit at different levels revealed juvenile delinquents had other factors which impact grit. A discussion about the meaning of labeling theory followed from the results, and recommendations to improve educational outcomes in juvenile detention centers were given.