This essay contests the prevalent view of Richard Wright as a proponent of violent black masculinity.  Beginning with Uncle Tom’s Children, I argue, Wright provides a radical critique of the very ‘macho’ violent wish-fulfillment he has been accused of endorsing.  Stories such as "Big Boy Leaves Home," "Down by the Riverside," "Long Black Song" and "Ethics of Living Jim Crow" underscore the cruel ironic bind of black masculinity under Jim Crow: Black male children can be punished as “men” for the slightest perceived misstep, even while grown Black men are forced to assume the permanent position of “boys,” forever deferential to white authority.  Wright confronts us with the trauma of black male vulnerability, while also interrogating the complex and contradictory psychological reactions and socio-political responses such vulnerability gives rise to.  His work grasps the impulse to black masculinism as an understandable response to the particular historical circumstances of Jim Crow, while at the same time underscoring the strategic liability of such violent and individualist reactions.  Ultimately, Wright suggests that it is only the concerted response of the larger black community that offers black boys and men alike a chance of meaningful resistance.