In 1966 Palestinian poet and activist Mahmoud Darwish published two essays, one titled, “Letter to a Negro,” and the other titled, “Second Letter to a Negro.” In them Darwish, a Palestinian citizen of Israel, wrote about how the writings of black Americans such as James Baldwin resonated deeply with him. But Darwish also insisted on distinguishing between the overt forms of racialized oppression experienced by black Americans and the more covert forms of oppression he faced at home. While a number of recent scholarly works have shed new light on how Palestinians and black Americans have compared their respective struggles for freedom with one another, the dominance of English-language sources in this body of scholarship has meant that important Palestinian perspectives have not yet been brought to the fore. In particular, the writings of Palestinian intellectuals in Israel who saw clear parallels between their own positionality as minoritized citizens and the positionality of black Americans have not yet been adequately investigated. I address this gap in the literature by tracing the ways in which Palestinian intellectuals in Israel engaged with multiple facets of the black American struggle for freedom through a close reading and analysis of Darwish’s two essays. I argue that Palestinian citizens of Israel understood that they, like black Americans, faced a modern, racialized system of oppression that had similar internal logics, albeit with different external manifestations. More importantly, I argue that these Palestinians drew upon the experiences and perspectives of black Americans in order to push back against the structures of racialized oppression they faced at home while seeking to connect transnationally to other minoritized and colonized peoples who were engaged in similar struggles. By showing how Palestinian citizens of Israel compared and contrasted the intertwined logics of racialized oppression both at home and abroad, this paper elucidates the deep transnational engagements of Palestinian citizens of Israel during an important—and often overlooked—period of history. By focusing on Palestinian writings in Arabic, this paper also provides fresh insights that can contribute to important and timely discussions developing among scholars in Middle Eastern studies, cultural studies, critical ethnic studies, decolonization studies, and American studies.