The ideal of the Socratic Gadfly has been an inspiration for a wide variety of activists, thinkers, and movements. That it is an inspiration for instigators of social change suggests the Gadfly is one example of what Sternberg and Soleimani Dashtaki call transformational wisdom: “wisdom applied at a level that makes a positive, meaningful, and potentially enduring difference to the world as a whole” (Sternberg & Soleimani Dashtaki, 2024, p. 2). Nevertheless, the diversity of causes for which the Gadfly has been enlisted, along with the apparent failures and grim fates of some paradigmatic cases, make it unclear who counts as a Gadfly and whether they better the world in ways that warrant being called transformationally wise. In this chapter I defend an account that both enables us to discriminate true Gadflies from pretenders and vindicates the Gadfly’s transformational wisdom, focusing especially on the Gadfly’s capacity to help sustain positive social change.