Community health workers (CHWs) have been bridging the gap between under-served populations and health care systems for centuries; however, their experiences are rarely recounted. The Miami Healthy Heart Initiative is a randomized control trial designed to examine the effectiveness of CHWs on reducing the risk for cardiovascular disease among Hispanics with poorly controlled diabetes in South Florida. This manuscript, told from the perspective of CHWs, is a summary of cases that were successful and some that did not achieve optimal outcomes. These case summaries include anecdotal data and clinical variables that demonstrate each patient's progress during the intervention.