If the phrase ?a picture has a thousand words,? holds truths, what then can be said about an icon, let alone one that crosscuts politics, culture, race, and domestic divides? The power of icons has both implicit and explicit power that reverberates in more than just the political sphere and the iconization of Barack Obama before and after his presidency is no exception. Against the backdrop of Freak Show Politics and the democratization of technologies, this study attempts to position the icon of Barack Obama between spectrum of its use a hegemonic tool to reflect propaganda all the way to its use as a democratic tool utilized to reflect popular bloc?s beliefs. While the normative justification for his victory in November 2008 is substantiated through his mass political appeal, this study investigate a less-researched contributor and consequence of Obama?s successful campaign through less traditional forms of artwork and photography. These images - evoking the dogma of hope, innovation, and change pictorially articulate the transformational resurgence of the mass? desire to find a prophetic leader in the midst of the political legacy left by prior administrations. This study also applies the business model and cycle of creating an iconic brand to provide further insights regarding the marketing and branding of the Barack Obama image and its possession of the message of change. Through pre to post election, this study explores the birth, life, and predicts the legacy of iconic image of Barack Obama and its implications on the role of the presidency in the years to come.