In this article, I summarize, through the use of two case studies, the anthropological contributions when working with farmworker–migrant youth who have become “gang-involved.” The Florida Institute for Community Studies (FICS) worked with a total of 65 youth and their families in a federal antigang initiative, with one session being held in a Presbyterian-based farmworker mission and another at a middle school. Both groups of youth live in rural Hillsborough County, Florida, with a lack of afterschool or other prosocial opportunities outside of school. I share my personal experiences and reflections on how I got involved in working with gangs, which had not been a priority for me in the past. One area of concern was our finding that youth were recruited into gangs and risky behaviors through friendship and familial networks. The school-based youth did not fare as well as the mission-based group, principally because of labeling by the school and the lack of autonomy of youth in a school setting to take ownership of the program. I provide recommendations for anthropologists working with youth who live “la vida loca” or the crazy life.