This study examined the aspirations formation of disadvantaged Jamaican male youths. The design of the study was a Type 3 holistic design which considered the global nature of multiple cases, and focused on the impact of work, family, school, peers and siblings on subjects1 aspirations. Six case studies were conducted using observations, focus groups, taped interviews and document inspection techniques. Data were analyzed using McCraken's coding techniques. The results showed that the youths' aspirations were leveled, reflected realities f their employment possibilities, and were patterned after their father's occupations. The youths' reluctance to raise their aspirations signals the need for Jamaican policy makers to address the problems caused by low aspirations among youths. Recommendations for further research are offered.