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Chris Kraus’ texts show a great fascination with the figure of the artist as loser, which is most famously the case with her 1997 cult novel I Love Dick. This article questions the strategies deployed by the writer to explore the paradoxical logic of the loser – starting with the idea of what, exactly, is meant by losing in a culture in which one rejects the standards that define winning. Kraus promotes the letter/diary as a deliberately minor literary mode, situating her work within an intellectual and artistic tradition that identifies itself with the margins of the literary and art worlds. Here, the artist thinks of herself in terms of rivalry: rivalry with her own ambitions as well as with the artistic institutions she tries to find a place in. By valorizing losing as a mode of authenticity, Chris Kraus brings to the fore a tradition of subversion within a world of various coded rivalries (between men and women, between overt and shameful desire, between artists in the art market, etc.) and in doing so establishes the art of losing as a radical ethical position.