The connection between political radicalization and political violence is often thought to follow “organic stages.” That is, radicalization is considered to be a progression leading to violence, after which time radicalization and violence evolve together dialectically. This ideal-typical process does correspond to historical evidence, and this article presents such evidence from the political contention in Palestine during the Mandate period. However, other historical evidence points to deviations from this ideal type. Evidence from political contention in pre-1921 Ireland and in pre-1960 Cyprus suggests two forms of such deviations. Irish history suggests that violence may be effectively introduced by political forces that at an earlier stage had not been part of the process of political contention at large; Cypriot history suggests that violence may be introduced through forces that were autonomous from the ongoing process of political contention even though organizationally part of it. The historical comparison at hand, furthermore, points to the increased role of historical contingency in the instances where the relation between political radicalization and political violence deviates from the ideal-typical form.