In this chapter, we explore transformational wisdom, as defined by Sternberg and Soleimani Dashtaki (2024). We propose that transformational wisdom has itself transformed over time, as illustrated by three iconic wisdom figures: Socrates, who (on Plato’s account) transformed modern Western philosophy; Ibn Sīnā (Avicenna)—less well-known in America—who transformed Islamic and Christian understandings of wisdom by integrating medicine, science, and theology through reason and allegory; and Mohandas (Mahatma) Gandhi, who transformed wisdom through political activism that fought against social injustice. We also consider several other figures like Aristotle, Sa’di, and Thich Nhat Hanh, who were influenced by earlier transformational wisdom and often are transformational themselves. We conclude by using a method developed by Deleuze and Guattari (1987) to show the multifaceted connections between the transformational wisdom of these three iconic wisdom exemplars and those who followed them, and their implications for understanding the development of transformational wisdom over time.