In this chapter, I discuss how the medieval Islamic Philosophers wrestled with issues to do with the role and function of expertise. I show how this leads them to an epistemological position I call ‘Islamic Moderate Evidentialism’ and show how it directly bears upon their political philosophy whereby the Prophet is thought to be the ideal political leader. I then move to a more contemporary context and note parallels of this thought in the mid-twentieth-century revolutionary Islamism of Sayyid Qutb and Abul A’la Maududi. I show how understanding this movement from the perspective of medieval Islamic Philosophy leads us to articulating a unique political position where both Perfectionist Liberal thought and Anarcho-Socialism sit together side by side.