The Anti-Jewish violence during the Civil War in Revolutionary Russia left many besprizorniki, children who were orphaned and homeless. The Bolshevik government worked closely with international Jewish ‘bourgeois organizations’ to set up Jewish orphan homes across the country. This paper looks at the Bolshevik’s doctrine of engineering ‘the new citizen’ and examines the dilemmas and controversies associated with its implementation in a Jewish school context. In particular, the paper considers the case of 300 orphaned children who were transported from the territories beyond the Pale of settlement in the Ukraine to the city of St Petersburg in the beginning of 1920s with the help of the American philanthropic organisation known as the Joint. Zusman Kiselgof, a well-known Yiddish ethnologist, led the school. There, the Bolshevik’s doctrine was scrutinized through the lens of Jewish, national, radical ideas. An urban space, where rural ethnical representations were incorporated, was created. This paper draws upon Russian and Yiddish archival sources and applies some of the leading Soviet psychologist, Lev Vygotsky’s concepts, in an effort to understand how those alternative ideas about education were put together to generate a new socialist culture of schooling in an urban setting.