Advising an urban FFA chapter can be a challenge for urban agriculture teachers. The contextual differences between the rural-oriented FFA and urban FFA members can make bridging the gap difficult. This narrative study sought to explore how the urban context shapes the work of an FFA chapter from the perspectives of two FFA advisors at the same school. Both advisors had the same viewpoint about what experiences their FFA members should have, which included competitions and events beyond the local chapter level. Yet, they struggled to meet this goal. Their FFA members who attended the National FFA Convention discussed the need to feed local, food insecure people as an opportunity for their FFA chapter. This revelation did not make the advisors feel more confident; rather, they were still frustrated that their members could not find success beyond the chapter level in FFA activities such as career development events (CDEs) and supervised agricultural experience programs (SAEs). This meant that the definition of success for the FFA Chapter fell to the FFA advisors and not their members. Implications from this research include the role of advisors' past experiences in shaping how they conceptualize their FFA chapter activities and success.