This thematic biography demonstrates how Stephen Douglas’s path from a conflicted youth in Vermont to dim prospects in New York to overnight stardom in Illinois led to his identification with the Democratic Party and his belief that the federal government should respect the diversity of states and territories. His relationships with his mother, sister, teachers, brothers-in-law, other men and two wives are explored in depth. When he conducted the first cross-country campaign by a presidential candidate in American history, few among the hundreds of thousands that saw him in 1860 knew that his wife and he had just lost their infant daughter or that Douglas controlled a large Mississippi slave plantation. His story illuminates the gap between democracy then and today. The book draws on a variety of previously unexamined sources.