Farmers markets play an important role within local food systems and short food supply chains (SFSCs); they create community connections. While the number of farmers markets has increased dramatically since 1994, many markets fail, and it is unclear why. Little is known about the influence of leadership practices on their success and decline. This qualitative case study explored how leadership influences factors contributing to success and failure. The first objective explored patterns contributing to the success and failure. The second objective analyzed markets through different lenses of leadership. The study applied a leadership hexad (Jackson et al., 2018); adaptive leadership (Heifetz et al., 2009); and good-to-great leadership principles (Collins, 2011). Findings revealed surging operational changes, strong support in the SFSC, and the need for stabilizing forces. The six lenses of Jackson et al.’s leadership hexad generated nuanced findings about the influences of vendors, champions, and partnerships; the role of managers in supporting the community and entrepreneurship; confusing nature of ownership; planning for succession; surviving the startup phase; professionalizing farmers market management; co-constructing leadership with the community and vendors; evolving the purpose; and leveraging the purpose of farmers markets. Recommendations for future practice include professional development leadership pipelines.