E. H. Carr’s relationship to realism is more complicated than the standard descriptions of it would have us believe. Based on his The Twenty Years’ Crisis, the first section of this chapter highlights two points on this relationship. First, Carr does not present a clear definition of realism (or utopianism). Second, in a self-contradictory manner, he depicts utopianism and realism both as unmixable belief systems and realities and as always synthesized, or else synthesizable, ones. Indeed, throughout Crisis, Carr offers various descriptive and prescriptive syntheses of utopianism and realism. In this context, his critique of utopianism often turns out to be a critique of realism. The second section describes the “utopian” schemes for a lasting peace Carr proposes in his Conditions of Peace and Nationalism and After. The third section focuses on Carr’s version of “the first great debate,” which has played an oversized role in shaping the mythical image of realism as the level-headed doctrine that triumphed over (an imagined) utopianism (a.k.a. idealism or liberalism). The chapter concludes that Carr’s unclear definition of realism and utopianism, as well as his version of the “great debate” between them, rendered realism’s conceptual boundaries indeterminate from the outset.