July 4, 1776 marks the national beginnings of the United States and is celebrated as the date of its independence from the imperial dominion of the United Kingdom. This turning point in the history of the nation is accepted as the genesis of the American freedom that champions the unassailable rights of life, liberty, and the pursuit of happiness. Amidst the general enthusiasm for freedom, however, the existence of slavery stood out as the ultimate paradox which the new nation had to contend with. Contrary to the accepted historiographical explanations for the incongruous presence of slavery in this land of freedom, the article claims that the principles that defined the US citizenry also drew a racial boundary between white and black communities where whiteness, inflected by nationhood, was held to be coterminous with being American, while other (colored) identities were hyphenated incessantly. The first part of the article addresses the teleological and apologetic explanations for the slavery problem and argues against them by giving a detailed analysis of the inconsistent attitudes of the abolitionist politicians and communities towards African-American populations. The second part of the article studies the black responses to American freedom and Frederick Douglass's famous speech that excoriates the hypocrisies coiled in the founding principles of the nation.