Anyone with an interest in 20th-century physics has heard the name of John A. Wheeler (1911-2008), but, if we were to ask what he actually did over the course of his long career and how that relates to the eminent status usually accorded to him, the answer would often be rather confused. Luckily, Wheeler also left a vast archive that allows us to reconstruct his original ideas, ambitious aims, peculiar methodology, and fruitful suggestions. In this talk, in the light of Wheeler's notebooks and other archival materials, I will sketch his trajectory roughly from the early 1950s, when his attention first turned to general relativity, to the early 1980s, when he enunciated his radical "law without law" and the main traits of the later "it from bit" made their appearance. As Wheeler's questions became more and more ambitious, he also tried to establish dialogues with other disciplines, among which biochemistry, logic, and the history of philosophy. I will also detail some of these transdisciplinary dialogues and make a few methodological considerations on how to deal with them, both conceptually and historiographically.