The militaries’ economic role(s) in the Middle East have attracted much attention since the 2011 Arab uprisings. Specifically, The Egyptian Armed Forces (EAF) had been singled out as running a “business empire” with an incredibly wide-ranged statistic of “5-40% of the economy,” circulating in the literature. Obviously, one should ask is the military business market share as small as 5% or as big as 40% then? Or, more reasonably, has that share been oscillating and not monolithically the same, since 1952, as the literature currently have us believe? In triangulating the evidence to address the question of Middle East militaries' economic roles, this paper locates Turkey, Egypt and Israel together within the general political-economy phenomenon of the oscillation that took place as the three countries transitioned from welfare states with state-led enterprises into experimentations in free market economy. No study has paired these three countries’ trajectories together to systematically show similarities and differences. More specifically, the paper argues that in establishing the National Service Products Organization (NSPO) in 1978, to perform post-Peace Treaty developmental economic activities, Egypt was only mimicking a similar establishment of Turkey’s own Armed Forces Pension Fund (OYAK) of 1960, that was set, by law, following mutiny in the Turkish military, against Menderes policies that in the name of civilian control, cut resources for the military as a class, albeit within an overall entrepreneurially rising Turkish bourgeoisie in the 1950s. Sadat avoided such civil-military agitations by re-defining the military’s “developmental role” in a peace economy, thereby adopting aspects of Turkey’s model. Moreover, the Egypt’s military is equally compared to two traditions of “self-sufficiency” and “strategic sectors” of the Israeli Defense Forces (IDF), that currently dominate the High Tech business as a “strategic domain.” Thus, in this paper’s conceptualization, the three countries are to be understood within a Dynamic Regional Order that includes practices in the Middle East at large. The paper locates the very paradox of three armies’ contemporary neoliberal economic enterprises in the longer historical trajectory of war and peace economies; developmental and “modernization” literature; and recommendations for what was deemed “sound civil-military relations,” back at the time. The research findings tell, in in novel ways, the shared inception stories of military economic enterprises and their current contemporary perils. Methods for this comparative research design include examining primary documents, laws, media coverage, and anthropological ethnographic fieldwork interviewing in Turkey, Egypt and Israel on research trips (2011-2016).