My essay aims to develop my authorial map-account of Martin Duberman's various educational paradigms manifest in his experimental seminars at Princeton University, Hunter College, and Lehman College CUNY, 1966-1971 (and beyond) that I abstracted from his claims about his innovative educational teaching. I tried to develop a terrain of educational philosophical paradigms that shaped his goals, judgments, definitions of success, frustrations, and so on, and engage in a dialogic analysis of this terrain. His innovative pedagogy was driven by diverse and often conflicting educational philosophies involving democracy, dialogism, and therapy, among other values. I discuss the synergies and conflicts of these values in Duberman's pedagogy.