This article advocates a radicalized theoretical construction of community service learning. To accomplish this radicalization, I initially take up a discussion of traditional understandings of CSL rooted in pragmatic/progressive thought. I then suggest that this traditional structural foundation can be radicalized by incorporating Deborah Britzman's (1998) “difficult knowledge” and Cornell West's (1989) historic catastrophe into that traditional structure. In conclusion, I discuss the implications that such a radicalized understanding of CSL entails.