In his monograph entitled The Wages of Oil, the American political scientist Michael Herb argues that Kuwait’s high degree of political participation, relative to the neighboring Gulf states, owes itself to the Iraqi threat on two occasions (first in 1961, then the Iraqi Occupation in 1990). The resultant political institution derived from these two episodes of external threat is Kuwait’s National Assembly, which sets the stage for the ruling family’s “[in]ability to return to absolutism”. Such an irreversible trajectory is indicative of “path dependence” in political studies, which specifies that institutions and policies have a tendency towards inertia. In other words, when a political path is set on its course, it requires significant effort to divert them elsewhere, constraining future choices in the process. By analyzing windows of possible change, known as “critical junctures” in a path-dependent model, this paper seeks to compare the regime-building trajectories in Kuwait and Oman. Two critical junctures are singled out in order to decipher the room for political participation and regime resilience. First, the context that led to state-building (1961 for Kuwait, and 1970 for Oman), and second, the impact of the 2011 Arab Spring, which generated civic pressures but resulted in little genuine reform. This paper will show that regime resilience was reinforced at the onset of state-building, following a path-dependent model which prescribes long periods of stability but also punctuated by brief phases of institutional flux. Personalized sultanistic rule in Oman with little leeway for civil liberties meant that situations of flux had higher stakes. For Kuwait, the regime built on tenets of joint governance and pluralism allows a degree of political maneuvering, but only to a level acceptable to the executive power. This paper will also consider how al-Nahda (the Renaissance or the Awakening) in both Kuwait and Oman is recast under different myths that set the stage for the chosen regime type. The notion of path dependence is then reassessed in terms of structure and agency, with the latter being increasingly noticeable in an active citizenry.