Albeit Latin pilgrimages and military expeditions to the Levant during the High Middle Ages have often been portrayed as archetypal clashes between the putatively monolithic blocks of Christianity and Islam, the historical record describes a dynamic geopolitical landscape wherein political factions cooperated and competed across a meta-ethnic frontier (a biocultural boundary between two or more human groups). The present chapter qualitatively reviews these complexities, thereafter quantitatively demonstrating a cyclical oscillation wherein victory and unity are inversely correlated. This chapter’s macrohistorical analyses offer empirical evidence that: (1) Turco-Saracen within-group competition facilitated Latin victories; (2) Latin victories over Turco-Saracen factions facilitated Latin within-group competition; and (3) Latin within-group competition facilitated Turco-Saracen victories. This historical period then perfectly illustrates Evrigenis’ negative association as described in the quote above. A broadly shared cultural heritage and common religion were not always sufficient to keep these groups bound together and clearly demarcated from one another. Triumph over a common foe relaxed bonds; defeat by such a foe strengthened them. When on their heels and behind their battlements, either group assumed the proportions of a monolith; like a sedimentary rock whose layers are bound by pressure. However, victory slowly undermined solidarity, relaxing these pressures, exposing underlying layers of association.