Building on the rise of family history and migration studies as vibrant new modes for narrating American, Middle Eastern, and Jewish history, this paper traces the points of convergence and divergence between the lives of my Muslim father and his Tunisian Jewish teacher over the post-WWII decade that coincided with the decolonization of Tunisia. Born in 1941, my father left Tunisia in 1961 with the aid of an American government scholarship designed to orient postcolonial “Third World” students towards the United States. By encouraging him to apply for this scholarship, David Errera played a decisive role in what proved to be the fundamental event of my father’s life: his migration to the U.S. and education as a petroleum engineer at the University of Tulsa. Errera was descended from the Livornese Sephardic diaspora whose organized presence in Tunisia dates back to the late seventeenth century. Like Albert Memmi, he was imprisoned as a young man in a German labor camp in Tunis during the Nazi occupation of North Africa, became a teacher (of English) after the war at the Lycée des garçons de Sousse, and wrote for the Tunisian newspapers La Presse, La dépêche tunisienne, and Le Petit Matin. WWII changed everything for both men. Decolonization and the rise of Cold War ideological proxy warfare created a path for my father to migrate to the U.S. and pursue his dream of becoming a chemical engineer. For his part, Errera (and other Tunisian Jews) encountered an increasingly tenuous place in the new postwar (and eventually postcolonial) Tunisian society. Opportunities for social advancement like entering the teaching profession were available, but they were tied to the perpetuation of French cultural and institutional influence in Tunisia. Perhaps sensing the decline of that influence, Errera himself increasingly turned toward the U.S. as a vehicle for mediating his vision of Tunisia’s postcolonial future. Tensions over Israel, Algerian independence, and the 1961 Bizerte crisis with France ultimately overwhelmed that pluralist vision. Errera made his own exit from Tunisia in 1962, therebv converging in a paradoxical way with my father’s story – though his reasons for leaving may have extended beyond anti-Semitism. Using sources drawn from family papers, the archives of father’s school, newspapers, and French public records, this paper reconstructs the intersecting fates of two sons of Tunisia as they navigated the headwinds of life after WWII and independence.