The first biography of an eminent historian of South Africa Bill Freund, the late social historian and leading analyst of African history, passed away in 2020 soon after finishing his autobiography. Often described as the academy’s ‘outsider insider’, he was an eminent South African historian who published prodigiously in the areas of labour, capital and economic history. What influenced this American-educated academic to become such an astute and trusted observer of the political economy in Africa? We follow Bill’s intellectual journey from a modest Jewish home in Chicago in the 1950s to the Universities of Chicago, Yale, Ahmadu Bello University in Nigeria and Dar-es-Salaam, Tanzania, and finally to a permanent teaching position at the University of KwaZulu-Natal in Durban, South Africa. Peppered in between the commentaries on academic life are stories of his travels, poems he wrote for loved ones, and endearing anecdotes of friendships that shaped his life. As an ‘outsider’, both in the United States and abroad, he is able to offer rich insights into the world of Africanists and their scholarship on different continents. His thoughtful and balanced observations on late- and post-apartheid South Africa are especially interesting and refreshing. This posthumously published autobiography will give deeper insight into this unusual man and the world that shaped him – and which he in turn influenced through a deep commitment to rigorous scholarship. It includes a select bibliography of Bill Freund’s many publications as well as a foreword by Robert Morrell on the making of this autobiography.