With respect to Benjamin's treatments of the work of art and his historiographical method, Adorno accuses Benjamin of not being dialectical enough and of inadequate theorizing. This article argues that Adorno's blanket prescription for more dialectics covers over a chiastic relationship between his particular concern in each case. On one hand, Adorno worries that Benjamin gives over the artwork to ideological narratives. On the other hand, Adorno is concerned that Benjamin's historical materialism refuses historical narrative, which is precisely where Benjamin locates ideology. Indeed the disruptive potential that Adorno grants the artwork with respect to social and political ideology thus corresponds to the disruptive potential that Benjamin ascribes to his historical materialism with respect to historicist ideology. In this context the article considers the nature of autonomy for Benjamin and Adorno and its relationship to subversion, disruption, and redemption.