Prior to 1960, presidential nominees were largely selected in the infamous "smoke filled rooms" of state party conventions. In 1960 two serious contenders for the Democratic nomination, Hubert Humphrey and John F. Kennedy, realized their weaknesses with party bosses that would make this path nearly impossible. For Kennedy his youth, his Catholic faith, and his aloofness toward party leaders would undermine his campaign. For Humphrey his strong positions on civil rights would cost him support in the vital South. This work focuses on the Wisconsin and West Virginia Primaries, the only two in which both candidates competed. Original manuscript sources illuminate the differences between Kennedy's well-financed, well-organized campaign and Humphrey's more amateurish effort. These sources, along with a wealth of newspaper sources, also offer fascinating anecdotes of life on the campaign trail.