In this essay, we describe our experiences working with a rebellious primary stakeholder, Sylvia, as evaluators of a district-wide safe schools program. Given the breadth of the program and its multiple target constituencies, we were confronted with the challenges of managing a large number of stakeholders, or those individuals and groups that could affect or be affected by the program's success or failure (Freeman, 1984). We describe the circumstances that gave rise to Sylvia's emergence as a rebel stakeholder and discuss the implications of her "rebellion" to the well-being of the program. We introduce the term "rebel stakeholder" to describe someone like Sylvia--ambitious, talented and well-meaning--who, despite their best intentions, can have a significant role in undermining the process of evaluation and have the potential to put programs at risk. We describe our role in working with Sylvia and other key district stakeholders to help get the program off the ground and the evaluation underway. We describe how Sylvia's invaluable involvement early on later proved to be detrimental to the long-term viability of the program. We describe the circumstances that resulted in Sylvia being barred from participating in any aspect of the program. Our reflections are informed by our review of transcripts and notes from interviews and meetings with key district stakeholders and notes from our meetings as an evaluation team. The events described herein occurred during the first 12 months of our work with the school district.