This essay examines the messianic desire that impacted the cultural products of German-speaking Europe so strongly during the 1910s and 1920s. It then problematizes that desire by arguing that a famous 1930s debate, ostensibly about the political aesthetic of those previous decades, actually had as its central nerve the configurations of the messianic seen there. In juxtaposing two fundamentally disparate ways of the thinking the messianic (in contemporary theory as well as in the art and literature of a distinct period), I aim to interrogate the dialectical and aporetic structures inherent in messianism, as well as the consequences of secular co-optations of Jewish and Christian models.