This chapter surveys the early history of the Democratic Party and traces Stephen Douglas and Jefferson Davis’s paths into national politics. First, it charts the rise of Jacksonian Democracy in the 1820s and 1830s, using the career of Martin Van Buren to highlight the strengths and weaknesses of the party’s cross-sectional coalition. Although successful in winning elections and notching policy victories, the Democratic Party suffered from ominous sectional divisions. These became especially alarming in the 1840s, just as Douglas and Davis entered Congress. Loyal to Jackson and devoted to the Democracy, Davis and Douglas entertained divergent visions for the party’s future. Douglas embraced the party’s populist rhetoric, muscular expansionism, and commitment to white men’s egalitarianism. Davis regarded the party as an instrument for protecting slavery by making preservation of masters’ property rights a national imperative. Friction between these rival Democrats shaped both men’s careers from the moment they stepped onto the national political stage.