Over a decade ago, when I studied in my dissertation the lives of three world-renowned philosophers, Bertrand Russell, Ludwig Wittgenstein, and Georg Henrik von Wright, my main sources were their published biographies and memoirs. Later on, when I came across the correspondence between Wittgenstein and von Wright, and realised how frankly and spontaneously they wrote to each other, I was fascinated and convinced of their friendship. Not only were they colleagues with a similar cultural background, who understood each other and each other’s work, but they also seemed to be trusted friends who freely shared their lives, fears, and joys in their letters. This paper sheds light on the surprising friendship of Wittgenstein and von Wright. It aims to show why they became friends by analysing their personalities, life choices and Wittgenstein’s legacy to von Wright drawing mainly, but not exclusively, on their correspondence, thus giving space to their own voices.