In this article I excavate and critique two dominant images of the international lawyer that emerge from the oeuvre of Martti Koskenniemi. In doing so, I hope to briefly shake the faith critical international legal thought so often invests in the potential of the subject. The first image is of the critical subject that emerges from From Apology to Utopia. She also happens to be a projection of the critic, governed by both elitism and unhappiness, for whom freedom is always both a constant and overarching possibility, and yet always embodied in a fleeting moment. By way of critique, I question whether this critic(al subject) may not unwittingly embed the very aspects of liberal legal and political thought that she seeks to challenge. The second image is of the professional lawyer, left on the shores of pragmatism. She emerges from my reading of Koskenniemi's The Gentle Civilizer, the 2005 Epilogue and his Kantian texts. She is constructed as Koskenniemi's critique is domesticated, taking a last, and perhaps futile, refuge in an ethics that is needed to buttress an identity which can aid international law's moral regeneration. Koskenniemi's writings urge today's international lawyers to put their sense of identity into question; this article asks which identities (and their possibilities) he embeds as he does so.