F. Scott Fitzgerald is valued for his contribution to literary arts, culture and his discussion of the American Dream. I argue that his discussion of the American Dream was a lens through which he gave readers access to political insights and an education about political philosophy, American politics, virtue, and reasoning. The American Dream, at its greatest, for Fitzgerald is a nation building myth but at its lowest is a dull materialistic construct. Throughout his works Fitzgerald connects philosophic ideas to the American Dream in attempts to educate and ennoble his readers. The ability to judge well is a critical piece of self-government that was a focus of Fitzgerald's throughout his body of work. In The Beautiful and Damned, by giving weight to Platonic ideals of beauty and goodness, and Platonic heuristics like the allegory of the cave he attempted to negate the detrimental effects of nihilism in America at his time and after. In The Great Gatsby, by presenting virtue of the contemplative life that could be cultivated by his readers, in his time, and including esoteric teachings on those virtues and values he attempted to negate the detrimental effects of materialism on the American dream. Finally, in The Last Tycoon, by articulating an American alternative to the philosopher-king he put forward a vision of statesmanship that could mitigate the effects of materialism and keep the American Dream alive against a socialist attack.