Jack was in for a tough battle. With the hesitancy over his youth and Catholic faith, and his sporadic support for liberal causes, winning favor with state party bosses who controlled many of the convention's state delegates would prove an amazing feat. There were only sixteen state primaries, so making contact with state leaders was essential. This was clearly different from his other campaigns, so plotting a course of action would take the organizational aptitude of Bobby Kennedy.

Kennedy needed the support of state leaders such as Chicago's Mayor Richard J. Daley, California Speaker Jesse Unruh, and Pennsylvania Governor David L. Lawrence, but he also needed support from primary voters. So Jack did what he had grown accustomed to doing over the past few years. He traveled. First he stopped in New Hampshire where the primary was scheduled for March 6, 1960. This New England territory was a certain win, since Adlai Stevenson and Stuart Symington had little hold on the state. Jack won 85 percent of the vote.

Campaigning in Wisconsin

Jack was also expected to win Indiana and Nebraska, but the Protestant state of Wisconsin posed a real challenge. This time, Kennedy had a challenger: the personable and well-liked Hubert Humphrey. Jack, however, had paved the way the year before with a sixteen-day tour of the state. Although the cold wreaked havoc on his back, for six weeks he walked the streets meeting and greeting the voters, many of whom gave him an unenthusiastic welcome. In the end, Jack's vigor paid off. On April 5, he narrowly beat Humphrey with 56.5 percent of the vote.

Proving his Viability in West Virginia

Although Wisconsin was a victory, there were still doubts about Kennedy's ability to win non-Catholic votes. The six districts he won in Wisconsin were composed mainly of Catholic voters, while Humphrey won the Protestant districts. In a sense, this was a defeat for Kennedy since it failed to prove his viability among non-Catholics in a national race. On the religious issue, the press turned out to be more of a hindrance than a help; they commonly mentioned his religion in news stories. This was frustrating to Jack, but he carried on. He hoped to put the issue to rest once and for all when he arrived in West Virginia, where only 4 percent of the state was Catholic. This time, Jack expected to enjoy a decisive victory over Humphrey and prove he had what it took.

Jack decided to address the religious issue head on. His first stop in West Virginia was in Charleston. From the steps of the post office, he openly discussed the issue. This was an important decision, considering that Humphrey was using the religious issue to his advantage. Humphrey had aptly adopted the theme song “Give Me That Old Time Religion,” and warned listeners that voting for a Catholic would mean a partnership with the pope. Jack, although frustrated, assured voters that church and state would remain separate under his leadership.

Jack needed all the help he could get. Jackie came along but campaigned for only a short time due to her pregnancy. Her mannerism and style of dress were impressive to voters, who viewed her as a type of American queen. Also on the campaign trail with Jack were his brother Ted, long-time friend Lem Billings, and brother-in-law Sargent Shriver. In a stroke of genius, Joe, working on the campaign from Hyannis Port, recommended that they send Franklin D. Roosevelt Jr. to campaign for Jack in West Virginia.

The state was surrounded by monuments memorializing FDR, so the presence of his son was a winning strategy. During Roosevelt's personal appearances, he praised Jack and contrasted Jack's heroic service in World War II with assertions that Humphrey was a draft dodger who had sought military deferments during the war. Humphrey was irate that the statements were not retracted after he informed Jack that physical disabilities had prevented his service. To the public, Jack made it clear that he had never approved the statements, but it was too little too late. The damage had been done to Humphrey's image.

Jack outspent Humphrey $34,000 to $25,000 — significant considering that votes were essentially for sale. Voters cast their votes according to the approved list of candidates named on their slate. The county boss, who determined the slates, backed the candidates who paid the most money. Jack could afford to pay, but Humphrey could not. On May 10, Kennedy won West Virginia by 60.8 to 39.2 percent.