This article examines the career of the educationalist, Conservative politician and published writer on education and politics, Rhodes Boyson (1925-2012). As an educationalist, Boyson established Highbury Grove Boys' Comprehensive School in Islington, North London: An inner-city school which was antithetical to the wave of progressivism in the 1960s and early 1970s. The article explores Boyson's educational approach and vision in greater depth than has been the case in previous publications about him and attempts to place him beyond the limitations of a caricature and offer some redemption, seeing him as a paradox: he was welded to educational traditions but at the same time had a vision which can be seen as forward-thinking. This duality, and the sense of Rhodes Boyson as a paradox, makes the Janus metaphor apposite.