This article poses a synthetic analytical approach to casing migratory projects that set out to effectuate a redistribution of power and resources: migration as contentious politics. Contentious migration is presented as an attempt by a collective to mobilize adequate political leverage to advance claims in the location of immigration through spatial relocation and demographic change. To demonstrate the analytical leverage of this approach, this article then conducts a case study of the under-examined Hechalutz settlement movement active in North America between 1905 and 1953, which facilitated the settler migration of American youth to rural agricultural colonies on the colonial frontiers of late-Ottoman and British Mandatory Palestine. It draws on extensive, original findings in colony and national archives, examining official movement publications, correspondences, emissary notes, meeting minutes and daily records from the training farms across North America, diaries, and obituaries. Through eventful analysis, the article explicates three salient mechanisms of the mobilization for contentious migration: (1) environmental (attributing political opportunity and threat); (2) relational (forging networks, as a proxy for diffusion and organizational cohesion); and (3) cognitive (devising resonant diagnostic, prognostic, and motivational framings).