Along with the rooming house the family also ran a poolroom and O'Brien's Cafe and Restaurant. Myra O'Brien did the cooking—her clam chowder, beef stew and soda bread were locally renowned—and Larry did the hustling, standing on a Coke box at age 10 and taking on all comers at eight ball. At home the O'Brien kitchen became a political hotbed where such luminaries as Boston Mayor James Michael Curley and U.S. Senator David Ignatius Walsh held forth. In rapt wonder, Larry listened as they carried on like IRA conspirators. Not surprisingly, in high school his chief interest was debating, which he pursued with a flair that would have made Curley, his hero and the flamboyant archetype of The Last Hurrah, proud.
O'Brien recalls, "Our kitchen used to be the place where some of the boys would meet, and my father would say, 'All right, now we'll get the signatures.' It was organizational politics, signatures on petitions, door-to-door canvassing. He was a great planner—all the things I wound up being involved in myself."
While working at night toward his law degree from the local branch of Northeastern University, he tended the mahogany bar at O'Brien's Cafe by day, chinning for hours with ward heelers and candidates of every stripe. Clearly, lobbying and not law was his passion, and at 22 he became the chairman of his local ward and president of the Hotel & Restaurant Employees Union. As a neighborhood saying put it, when it came to getting out the vote young Larry O'Brien "could talk a dog off a meat wagon."
As it turned out, the union job was the only elective office O'Brien ever ran for, an ironic turn for the man Jack Kennedy called "the best election man in the business."
Their alliance began in 1951, when O'Brien organized Massachusetts for Kennedy, who was making his first bid for the Senate. Then 33, the same age as Kennedy, O'Brien was a wellspring of political innovations. Things, little things, like teas and Christmas cards and telephone campaigns became his vehicles for shaping big events. And always he followed his No. 1 political dictum: there's nothing like ringing a doorbell.
It was "dog work," he once confessed, but as detailed in a 70-page handbook called O'Brien's Manual, it became the electioneer's bible. In recent years everyone from Barry Goldwater to former British Prime Minister Harold Wilson and Philippine President Ferdinand Marcos has employed the O'Brien method. Goldwater may have missed the main thrust of the manual when he used it for his unsuccessful 1964 Presidential campaign. O'Brien sums it up thusly: "Keep it simple, avoid the slick, and work like hell."
How well the O'Brien approach works was first demonstrated when Kennedy won the Senate seat in 1952, upsetting the initial heavy favorite, Henry Cabot Lodge. And then it was on to the White House, ringing doorbells all the way, and the heady days of the New Frontier. Along the way O'Brien picked up enough material to pen a bestseller. Patriarch Joseph Kennedy, for example, passed on some sage advice about how to keep from being unduly influenced by prestigious people in or out of politics. "Whenever you're dealing with someone important to you," the old man said, "picture him sitting there in a suit of long red underwear."
As for influence peddling, O'Brien learned early on that it helps to see things from another man's point of view, even if the other man happens to be a hidebound NBA owner. Once, when stumping for Kennedy in the back hills of West Virginia, O'Brien began wooing a local leader with his usual pitch for a New America. The man listened for a while and then said bluntly, "I'm not interested in the White House. I'm interested in the courthouse."
Such lessons have taught O'Brien to be a realist. He doubts there ever was a Camelot, as least not in his terms. "I don't know what I'm doing with this crowd," he once said of the Kennedy clan. "I don't even fit the pattern. I didn't go to Harvard. I don't play touch football. In sports, I am pretty much of a spectator."
Burdened by 20/400 eyesight and a complexion that turns red as quickly as a stoplight if he lingers in the sun too long, O'Brien is no outdoorsman. Or, as one friend put it, "Larry's not the kind of guy you'd throw into the swimming pool." Jackie Kennedy understood. No great slotback herself, she preferred to sit in the shade with O'Brien during all those Hyannis football games. In return, on the campaign trail, where she did not think she should be seen smoking in public, Larry would sneak her a few furtive puffs every now and then.