This article applies a (micro)biographical approach to the life stories of two Ottoman orphans sent to Germany to receive vocational training during World War I, Ali and İsmail Dağlı. Coupling family archives, oral and visual sources with state documentation, I elaborate on the post-Ottoman afterlives of German know-how, education, and capital in the social and economic history of Turkey. Biographies of Dağlı brothers show that the successors of both empires restored former channels of circulation of expertise, technology, and labor. Especially seen in the context of Jewish emigration, the life and work history of the brothers elucidate the positive reception of their German education, the importance of their position as “cultural intermediaries,” and the extent of Turkish-German business entanglements.