The paper looks at the roots of the Arab Spring, the subsequently contentious political landscape, which emerged in post-revolutionary Middle East, and the series of conflicts and dizzying challenges, which have gripped much of the region. Principally, it examines, historically, the distinct combination of (structural, agential, and triggering) factors, which led to the Arab uprisings as well as the role of moderate, mass-based Islamist movements, principally the Egyptian Muslim Brotherhood (mb) and its offshoots, which managed to rise to power, in certain countries, after the downfall of Arab strongmen across the region. But, shortly after, to be followed by the unceremonious demise of Egypt’s Muslim Brotherhood (mb), and the ensuing region-wide backlash against its offshoots in 2013. The paper argues, after a careful examination of the structural roots of the 2010–11 Arab uprisings, that one of the principal pitfalls of the ruling Islamist parties was their inability to establish a credible mode of governance, which could decisively mark a break with the old order. They failed to provide an alternative economic agenda to address the structural maladies of the crony capitalism, which emerged on the heels of accelerating market-oriented reforms in the 1990s. The influence of Arab Sheikhdoms on Arab Transition Countries (atcs), and their support for ultra-conservative Salafi groups, further diluted the process of democratic transition, leading to, among other things, the breakdown of the political process in Egypt.