In this article, Boaz Tsabar explores the fundamental significance of relations of trust between educator and child in the work of renowned Polish-Jewish pedagogue, author, children's rights advocate, and orphanage director Janusz Korczak. The first part of the article investigates the existential importance of trust in a pedagogy that is based on humanistic-dialogical principles. The second and central part explores three ways in which Korczak strived to implement the element of trust in his educational work with children at the "Dom Sierot" orphanage in Warsaw: the first manifested in a renouncement of idealism coupled with a concrete demonstration of respect for students' actual life experience; the second in the creation and maintenance of a consistent and orderly pedagogical space so as to infuse pupils' lives with a sense of security and rational order; and the third in a refinement of reality to the level of a game while upholding the child's right to engage in trial-and-error within it. Finally, Tsabar discusses the fundamental importance of forgiveness in Korczak's concept of trust and concludes the article with an investigation of two implicit threats to the development of relations of trust in the contemporary public school system.