Every day, thousands of local government employees across the country serve, support and protect vulnerable youth in administering legislative policies and public programs. Unfortunately, little research has focused specifically on the role of these employees in implementing youth policies and programs, and even fewer studies have translated employees’ experiences into valuable lessons for the field of youth policy. To address this gap in the literature, this report analyzes the results of interviews with twelve City of Chicago government employees, each of whom work in child, family or youth programs, and explores their day-to-day experiences serving Chicago youth. Interview results find that the rise of the youth programs depended heavily on financial and political support from the mayor, as well as on the City government’s operation as a service funder. The ongoing success of the programs, on the other hand, relied on expert frontline staff and longterm mayoral support. This report concludes with four youth policy recommendations, and ultimately shows how local government employees’ nuanced policy knowledge can and should be used more effectively to inform youth policy decisions in the future.