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Tea & Telephones. It was one of the briefest retirements in political history. Within six months O'Brien was hard at work, organizing Massachusetts for John Kennedy, then a third-term Congressman and an unannounced aspirant to the Senate. Kennedy had known O'Brien casually for five years, had spotted him as a campaign organizer of rare talent. Within a year, O'Brien had recruited 350 secretaries, 18,000 volunteer Kennedy workers. By the time Kennedy formally announced his Senate candidacy, O'Brien was all ready with a purring statewide political machine. The O'Brien brain was a supermarket of political innovations: the campaign tea parties, with Kennedy's mother and sisters pouring (and an omnipresent guestbook to provide O'Brien with the names and addresses of potential campaign workers) ; the expanding "O'Brien Manual," a handbook of organizational instructions written in language that any amateur could understand; the O'Brien Home Telephone Technique, rounding up women volunteers who would each call all the people listed on a single page in the telephone book, ask for support and offer transportation to the polls. Explains O'Brien: "The key to this is the full utilization of womanpower. Normally, women are wasted in a campaign. They have children. They can't come to headquarters."
To the Kennedy team, O'Brien was and is more than a skillful political organizer. He has the experience and understanding to serve as a bridge between the Democratic Old Guard and the New Frontier. The bright, eager young men around Jack Kennedy have always baffled and often offended the Skeffingtons of Massachusetts; but Larry O'Brien can talk to politicians in their own language and win them over. "He was the essential transition man for us with the Old Guard," says Bobby Kennedy. At the same time, O'Brien was an invaluable professor of political science for the likes of Bobby, Kenny O'Donnell, Dick Donahue and other young members of the Kennedy group who were rank political amateurs in Kennedy's successful 1952 senatorial campaign. They have since become a close-knit, highly professional team that is known in Administration circles as "the Irish Mafia."
Big Thoughts. As a first-term Senator, Jack Kennedy had a legislative record that was nothing to brag about. But his political appeal was such that in 1956, when Democratic Presidential Nominee Adlai Stevenson threw the vice presidential nomination up for grabs at the party's Chicago convention, Kennedy made a wildly disorganized eleventh-hour attempt for the prize. He lost to Estes Kefauver, but by so narrow a margin that it set the Kennedyites to thinking really Big Thoughts. Recalls Larry O'Brien (who had not even attended the convention): "After that convention, we began to realize that Kennedy could go all the way."