This work sheds new light on the elevation of African Americans to the highest political offices of the land. The election of the Honorable President Barack H. Obama to the Office of the President of the United States of America was accomplished on a road paved by the blood, sweat and tears of many African Americans including John Jones, Oscar De Priest and several others. The stances taken by these leaders were forged from the historic struggles of race relations in America. It was their common belief in the American Dream and efforts to secure their share of that dream that led to the rise of African Americans in the political arena. The labors of these leaders created a legacy which extends from the Nineteenth Century in the State of Illinois to political elevations at the national level in the Twentieth Century. It also highlights the struggles endured by several of these leaders within their respective eras and provides insight into the handoffs which occurred between the leaders at the conclusions of their terms. Their efforts to organize the disenfranchised produced great victories in each era. These victories became the stepping stones for more victories in the succeeding eras. In doing so, these leaders laid a groundwork for perpetual success and a legacy which is second to none.