This research examines freedom within philosophical principles and American design to provide an argument to show how freedom within America has uprooted freedom from a sense of autonomous affinity and benign humane essence into a given and subjugated understanding. America’s desire for freedom through the Revolutionary War was a foundation towards freedom becoming a right rather than a relationship in the form of republicanism and America’s idealism of democracy. Further along the history of America, the Westward Expansion was a mirror to the core values of freedom within the Constitution and America, but in the originality of what was deemed ‘The Wild West.’ Still, it was reflected in the romanticism and Western culture of the period but precluded only the same fundamental discrimination found in traditional American principles.