This rhetorical analysis examines the attributes, ideologies and performance of Obafemi Awolowo during his very first experience at governance as premier of the defunct Western Region of Nigeria and, by extension, leader of his party, the Action Group. It gauges Awolowo’s political communication against the background of the contingent apprenticeship that he and other African nationalists were subjected to under the colonial rule. It, further, examines Awolowo’s zeal and enthusiasm at governance, with a view to determining his readiness for the onerous task of proving to the world that he, like his contemporaries, was capable of performing more creditably than the colonial masters, formerly in the saddle of leadership in Nigeria. The study forms part of the ramifications of the developmental study of Awolowo’s political rhetoric, during his entire political career. Thus, this study of Awolowo’s first experience at governance, from October 1, 1954 to 31 December 1959, has been lifted from the totality of the umbrella study of his full career, as a politician, from 1951 to 1983, undertaken by this same researcher. With the original intendment of the whole developmental study, 40 political speeches, delivered by Awolowo, during six periods of navigating the political terrain of Nigeria, were carefully chosen, for content analysis, via the proportional stratified sampling technique. Nine of these were in the compilation for the period under scrutiny. The purpose of this particular study was to determine how articulate Awolowo was with governance and how serious he was with his philosophy of democratic socialism. The hypothesis tested, in this study - whether any significant difference existed in issue salience, judging by Awolowo’s reactions to them – was answered in the affirmative. Awolowo was also discovered to have been very articulate as premier and was serious with the execution of his philosophy of democratic socialism, although he tended to be equivocal in the discussion of the philosophy.