This study examines the impact of John Dewey’s democratic educational principles on the reforms of the Lebanese educational system using data collected through semi-structured in-depth interviews, with open-ended questions, as part of case studies designed for this purpose. The participants in this study are all academics, facilitators, intellectuals and scholars of a Lebanese decent (n=30), undertaking full-time and part-time academic posts, involving learning and teaching activities at universities and other higher educational institutions/providers in Lebanon and in the diaspora (United States of America and Australia). As part of the case studies, the individual, personal, and professional teaching and learning journeys of the educators are sketched in details in relation to John Dewey’s four (4) key democratic educational reformative principles. Moreover, the current research study finally concludes by providing a realistic response to the following question that currently lingers in every academic Lebanese mind and on every Lebanese, scholar’s lips, namely, given Lebanon’s current liberal and relatively democratic educational system, are the Lebanese intellectual reformers truly given the opportunity to create a positive and constructive future vision for Lebanon through its educational system. The current chapter further provides a realistic and clear-cut description of the hurdles facing the current Lebanese educational system, including the scholars, intellectuals, and academics, residing in both Lebanon and in the diaspora. The current study further provides an elaboration on how such hurdles to actual and realistic reforms in Lebanon are impacting on the country’s brain drain phenomenon, as witnessed during the unfortunate latest Lebanese crisis (1975-1991), and post-crisis (1992-present) periods, which, in itself, act as a vicious circle, heavily contributing to the continuously deteriorating state of the current public Lebanese educational system.