The present study is a comparative analysis of two Jewish educators, well known figures before the Second World War, who responded in opposite ways to the same historical reality of oppression by choosing different avenues of resistance. The first figure is the world-renowned educator, paediatrician and children’s book writer Janusz Korczak. The second is the Bible teacher, Hebrew and Yiddish poet, Yitzhak Katzenelson. This comparison touches the very essence of an educator’s identity; it forces us to ask ourselves how we view educators. Do we see them as civil servants who obediently transfer the commonly accepted knowledge of their society to future generations or do we expect them to resist evil and lead their society to a better reality?