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With Larry O'Brien and his organization working as though their own lives were at stake, Kennedy won re-election to the Senate in 1958 by close to 900,000 votes, the biggest plurality in Massachusetts history. Kennedy's reputation as a prime vote getter—presumably on a national scale—was correspondingly enhanced. And so, in late February 1959, Jack Kennedy called a special presidential strategy session at his father's Palm Beach home. Present were Brothers Bobby and Teddy Kennedy, Brothers-in-Law Sarge Shriver and Steve Smith, Adviser Ted Sorensen—and Larry O'Brien. In this first formal planning for a Kennedy effort to reach the White House, O'Brien was assigned the job of establishing Kennedy organizations throughout the U.S.
Courthouse v. White House. Carrying out that assignment, O'Brien crossed the nation nine times, traveling 100.000 miles, talking deep into every night, stoking himself with three packs of Pall Malls, a Niagara of black coffee each day. He set up the local organizations, staffed mostly by enthusiastic amateurs in the states where Kennedy had to win presidential primaries to have any real hope for the Democratic nomination. O'Brien could also talk turkey with such patronage-minded politicans as a local West Virginia leader who told him bluntly: "I'm not interested in the White House. I'm interested in the courthouse."
The primaries won, O'Brien was in Los Angeles setting up Kennedy headquarters a full month before the Democrats met to choose their candidate for President. In Los Angeles, O'Brien's elaborate telephone and walkie-talkie system of instant, 24-hour communication with the convention floor and each state delegation headquarters was a marvel of modern political efficiency. After the convention, O'Brien applied all his tried and true organizational techniques to Kennedy's winning campaign against Republican Richard Nixon. "It was dog work," he recalls, "but it was worthwhile: it worked." Jack Kennedy's own post-election appraisal of O'Brien: "The best election man in the business."
Immediately after Election Day, O'Brien drew an arduous assignment: checking the qualifications, background, weak points and strong suits of nearly 10,000 prospective officials in the new Administration. One afternoon in Palm Beach, going over the lists of names with O'Brien, Kennedy casually notified him of his new job: "By the way, I think this role of congressional liaison is for you." As a graduate of both houses, Kennedy gave O'Brien a warning against the pitfalls of intimacy. "In politics," the President-elect told him, "you don't have friends. You have allies."