This study offers a rhetorical analysis of George Jackson’s Soledad Brother, informed by class critical and critical race theory. Recent rhetorical studies scholarship has taken up the problem of prisons, mass incarceration, and resultant issues of race, yet without paying attention to the nexus of black radicalism and criticisms of capital. This study views George Lester Jackson as a rhetorician in his own right and argues that his combination of critical race and class critical perspectives is an important move forward in the analysis of mass incarceration. Jackson is able to combine these ideas in a plain-writing style where he employs intimacy, distance, and the strategy of telling it like it is. He does this in epistolary form, calling forth a long tradition of persuasive public letter writing. At this study’s end, ideas of circulation re engaged to show the lines of influence Jackson has and may continue to have. Through rhetorical analysis of Soledad Brother, this study demonstrates the utility of uniting class critical criticism and critical race theory for rhetorical studies, and suggests further avenues of research consistent with this approach.