Objective: This article aims to analyze the concept of the teacher within conservative and progressive educational paradigms through a comparative examination of the philosophies of Ibn Jama’ah and John Dewey. The study addresses the contemporary crisis of teacher authority, wherein educators risk being diminished to mere technical facilitators of learning, while their pedagogical authority is caught in a tension between conservative domination and aimless progressive liberty. Method: Employing a qualitative library research methodology with a comparative-philosophical approach, the study utilizes Ibn Jama’ah’s Tazkirat al-Sami’ wa al-Mutakallim fi Adab al-‘Alim wa al-Muta’allim alongside John Dewey’s Democracy and Education and Experience and Education as primary sources. Data were examined via close reading, qualitative content analysis, conceptual analysis, and a critical comparison focusing on authority structures, teacher-student dynamics, ethics (adab), experiential learning, and pedagogical methods. Results: The findings reveal that Ibn Jama’ah conceptualizes the teacher as an ‘alim (scholar), a mu’addib (cultivator of character), and a moral-spiritual mentor whose authority is founded upon knowledge, adab, muraqabah (spiritual vigilance), muruah (dignity), haibah (reverence), compassion, and the responsibility for holistic student development. Conversely, Dewey envisions the teacher as a director of experiences, a facilitator of inquiry, an organizer of learning environments, and a guide for the social growth of students. Novelty: A comparative synthesis demonstrates that Ibn Jama’ah’s conservative educational model cannot be simplified as rigid and authoritarian, as it inherently incorporates principles of gentleness, pedagogical adaptation to student capacities, continuous evaluation, and a profound respect for the learner's dignity. Similarly, Dewey’s progressive education cannot be misconstrued as unguided freedom, given that the teacher retains a crucial role in imparting structure, direction, and educational value to the learning experience.