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Throughout his life, W.E.B. Du Bois frequently turned back to Reconstruction in order to think about his political present. Many of his accounts of the period, most famous among them his magisterial Black Reconstruction in America, present the moment of post-war Reconstruction as a “path-not-taken,” a missed opportunity, or a political future foreclosed. This paper makes sense of Du Bois’ writings by focusing on one particular aspect of the doomed Reconstruction project, the plan to provide land to freed slaves. Du Bois demonstrates how the failure to achieve a more equal distribution of land not only propelled white recapture of Southern politics, but also fostered the conditions for the rise of a new economic order and new ways of thinking about politics. I read his essays from the 1930s in order to sketch Du Bois’ understanding of how the new order emerged and what political conditions enabled this modern capitalist order to take hold. Finally, I turn to Du Bois’ 1911 novel, The Quest for the Silver Fleece, to detail the political-economic arrangement that continued to oppress workers black and white up through Du Bois’ moment. In the novel, Du Bois offers a “counter-history” of the Gilded Age that provincializes federal politics as the proper site for combating political corruption and oppression. Only through local action and self-organization can the black tenants of the story achieve real emancipation. I conclude by reflecting on how these essays, novels, and treatises figure land as foundational for black freedom in the United States. For Du Bois land is important in the struggle for black freedom because land was a crucial form of capital, signified a particular place of oppression, and constructed a common aesthetic world worth preserving.