In this paper, the notion of pearl diving as a metaphor for historical methodology is explored as a possible conceptual contribution to pedagogical thinking and practice. Pearl diving in the thinking of Hannah Arendt and Walter Benjamin refers to a process of bringing to life and coming to terms with a fragmented past, and requires of the thinker a form of Homeric impartiality. This they contrast with the processual and functional modern understanding of historiography, where events and things are subsumed by a causal linearity. According to Arendt and Benjamin, our past cannot be understood as though in one piece, but should rather be engaged as fragmented and crystallised into events—or pearls—which can be retrieved and can help us to illuminate our past and to understand our present. This paper considers what such an approach would entail for pedagogical theory and practice, as well as for the work of the pedagogical thinker and the teacher.