There was a recklessness and perversity in Headlam which hung about him all his life, Caustic expression, straining after effect, and the bald statement of paradoxes as though they were the commonplace of all but the insensitive or the malign, while sometimes acceptable in youth are rarely so in the more mature, and Headlam accumulated large numbers of influential opponents. His own biographer – in a work read and approved by Headlam – referred to ‘an imp of mischief’ that seemed to rest upon him. Yet the same work speaks also of his courage, and this was echoed by others who have assessed his life and ideas. To many of his contemporaries he seemed eccentric: a clergyman who praised the insights of atheists and secularists, a member of the ‘respectable’ professions who mixed in theatrical and artistic circles, who embraced Fabian Socialism, who supported outcasts like the Ritualist priests prosecuted under the Public Worship Regulation Act, and who befriended Oscar Wilde at the time of his trial. Headlam actually revelled in the seeming incompatibilities. ‘It is because we are Communicants that we go to the Theatre’, he said on one occasion; ‘because we are Priests that we believe in Progress’. To the modern ear such sentiments will not seem strange. To late-Victorian sensibilities they could sound profoundly shocking, and Headlam's vaunting tone did not help. He may, indeed, be rightly accused of poor judgment over the expression of his ideas; for ideas, to be influential, have in some measure to be acceptable to the generation who receive them, and Headlam lacked both the historical sense and the balance of temperament needed to adjust his opinions to the expectations and common assumptions of the Church and the society he served.