This paper explores the history of the Muslim Brotherhood's ideological development, periodizing it into the organization's formative period and two following generations. Using this framework, it describes how the formative period influenced the second and third generations and how the discourse between various factions within each generation of the Brotherhood resulted in a new trajectory for each subsequent generation. In order to do so, this paper compares and contrasts the views of Ḥasan al-Bannā, the founder of the organization, to those of his first three successors: Sayyid Quṭb, who succeeded al-Bannā as the organization’s chief ideologue as well as Ḥasan al-Huḍeibī and ‘Umar al-Tilmisānī, the second and third murshids (General Guides). The main points of comparison are the four men’s views on three key issues related to their understanding of the so-called “Islamic state,” the way of establishing it, and their understanding of sharia. For this comparison, the paper uses the original Arabic versions of al-Bannā, Quṭb and al-Huḍeibī’s writings. As for ‘Umar al-Tilmisānī, it relies mainly on two lengthy newspaper interviews in which he discussed issues related to these three points. The paper also makes use of the writings of the former Muslim Brotherhood senior official ‘Abd al-Munʻim Abū al-Futūḥ who published his “testimony” on the evolution of the Islamist movement in Egypt. The paper argues that the changes in the Muslim Brotherhood ideology under Nasser and Sadat’s regimes had their roots in ambiguities in al-Bannā’s teachings. Both radicals and gradualists found models for their respective political behavior in al-Bannā’s rhetoric and leadership. In addition, the paper argues that the Muslim Brotherhood's complex relationship with the state throughout its history has driven many of its ideological shifts, oscillating between moderation and radicalization based two main variables: the type of the Egyptian regime under which the Muslim Brotherhood operated and the strategic adaptation of the organization’s leadership to the changing political circumstances.