When Jack asked Torby Macdonald what he thought of his running for Congress, his former college roommate—who’d grown up in a town near Boston—flatly stated that if his friend ran, he’d win.
Of all Jack’s best pals, Red Fay was the sharpest in seeing Jack’s inner directedness. When Jack told him of the pressure he was getting from his father—“I tell you, Dad is ready right now and can’t understand why his fine son Jack isn’t ready”—Fay understood that that wasn’t actually the whole story. “Although Jack shammed indifference to the whole idea of a political career, there was an underlying determination to get started on what he considered a very serious obligation. I wasn’t surprised early in 1946 when he made a very serious decision to run for Congress—and when he asked me to come east to campaign for him, I came.”
It was about this time that he met a new friend, Charlie Bartlett, down in Florida. “We were down there after the war, and, you know, gorgeous women were all getting divorces down there, and they were really good-looking girls. It was very upbeat, the whole thing, and I went to Palm Beach. My family lived in Hobe Sound. We drove down for the evening and went to this place called Taboo. And they had an orchestra and I was with a very, very pretty girl who was getting a divorce and it turned out she knew Jack and Jack came over and sat down and started telling me about his plans to go into politics. And I said, ‘Well, I’m getting ready to go into the newspaper business.’ And he said, ‘Well, you know, I’ve been there now and I haven’t been very deep but I have to tell you, you don’t get anything done. You can’t make changes. There’s no impact. I’m going to go into politics and see if you can really do anything.’ “
Bartlett, a sixth-generation Yalie, would be Jack’s close friend from that day forward.
Jack knew the leap he was taking in running for Congress. “I had never lived very much in the district,” he admitted years later. “My roots were there, my family roots were there. But I had lived in New York for ten years and on top of that I had gone to Harvard, not a particularly popular institution at that time in the 11th Congressional District. But I started early, in my opinion the most important key to political success, in December before the primary election next June.”
Charlie Bartlett recalled the conversation they had. “He was very clear about his decision to go into Congress. Sometimes you read that he was a reluctant figure being dragooned into politics by his father. I really didn’t get that impression at all. I gathered that it was a wholesome, full-blown wish on his own part.”
Jack Kennedy’s own thoughts support his friend’s memory: “A reporter is reporting what happens, he’s not making it happen, even the good reporters, the ones that are really fascinated by what happens and who find real stimulus by putting their noses into the center of the action, even they in a sense are in a secondary profession. It’s reporting what happens, but it isn’t participating.”
By the time he made his decision, Jack, at the age of twenty-eight, possessed a level of intellectual preparation for public office uncommon even to seasoned career politicians. He had wrestled with the big-picture issues of war and peace in the 1930s, had survived the most extreme hazards of war, and been a firsthand observer of major international events. What he lacked was any practical grounding in the business of politics.
The fact that his father would take care of what the political types call the “wholesale”—the media, the press relations—hardly let him off the hook. The relentless workaday demands of a campaign lay ahead. He, the candidate, had to be the one to master the “retail,” which meant not just meeting voters one on one and winning them over, but inspiring them to join the effort. If you couldn’t connect with voters, then your other advantages, in the end, counted for little.
With the help of a local PR firm, Jack would soon be making the rounds of community groups: VFW and American Legion posts, Lions and Rotary Club meetings, communion breakfasts and Holy Name societies. This was a new world to him. But it was a necessary part of achieving his ambition, and he did it all. Writing his stump speech himself, he drew on his recent travels as a reporter in Great Britain and Germany, but always made sure to emphasize his recent stopover in Ireland.
Simultaneously, Jack decided to teach himself about being Irish. The diary he’d been keeping in Europe now contained a number of scribbled book titles accompanied by their Dewey decimal numbers. He’d always liked to connect to knowledge through reading, and, on that score, nothing had changed. Ireland and the President of the United States, Ireland in America, Ireland’s Contribution to the Law, and Irish American History of the US are some of the volumes he listed.
He was also soliciting the reactions of local political figures to his potential candidacy. But when he called on them, especially the Irish ones, he wasn’t just making the mandatory courtesy visits, he was brushing up against the city’s history. “For all Irish immigrants, the way in Boston was clearly charted,” he dictated in a memo years later. “The doors of business were shut; the way to rise above being a laborer was politics.”
His own path, he acknowledged, had been a privileged one. Being third-generation and not first makes a difference. “I had in politics, to begin with, the great advantage of having a well-known name and that served me in good stead. Beyond that I was a stranger to begin with and I still have a notebook which is filled page after page with the names of all the new people I met back there in that first campaign.”
One of the new acquaintances was a fellow by the name of Dan O’Brien, who was skeptical about the young man’s chances. After meeting him, Jack came away with these jotted-down impressions: “Says I’ll be murdered—No personal experience—A personal district—Says I don’t know 300 people personally. Says I should become Mike Neville’s secretary. O’Brien says the attack on me will be—1. Inexperience 2. Injury to me: me . . . father’s reputation. He is the first man to bet me that I can’t win! An honest Irishman but a mistaken one.”
The candidate also recorded maxims that applied to the situation. Among them:
• In politics you don’t have friends—you have confederates.
• One day they feed you honey—the next will find fish caught in your throat.
• You can buy brains but you can’t buy—loyalty.
• The best politician is the man who does not think too much of the political consequence of his every act.
He also noted: “The one great failure of American government is the government of critics.” Making the rounds and learning the ropes, he’d quickly recognized, as every politician must, the impossibility of pleasing everyone.
Now, for the first time in his life, Jack needed to make friends on a basis other than compatibility. Living on Beacon Hill, a young bachelor with no fixed address beyond rooms in the historic Bellevue Hotel, he lacked roots in the local community and needed to establish himself. The most important task was to enlist supporters who’d spent their lives in the district and would come on board, willing to stand up for him. While you could always hire a few professionals, the vast army needed for a win had to be made up of volunteers, those who helped him because they decided to.
The first hire was Billy Sutton, four years older than Jack and just discharged from the army. His description of the Jack of those days was a thin, bright-eyed figure with his hair cut close on the sides. Billy—whom I got to know well many years later—said that Jack had reminded him of the young Charles Lindbergh.
Before the war Billy had made himself useful in local politics as a result of his job checking gas meters, which naturally put him in touch with a wide variety of people. But he was the kind of guy who loved talking to anyone, and so, with Billy as his guide, Jack began trudging up and down the three-deckers of the old neighborhoods, introducing himself and asking for support. The person most surprised by this was his father. What Joseph Kennedy had yet to realize was the way the navy had changed his second son. The young man who returned from the Solomon Islands was not the one who’d left for there in
early 1943, and a large part of the reason the experience so altered him was because it offered continual exposure to people unlike himself, from all over the country and from every walk of life.
The fact that he was a returning serviceman was a key factor from the start. Working-class fellows like Sutton—and, later, Dave Powers, who’d served with the Flying Tigers—were ready to accept a young rich guy who’d been awarded the Navy and Marine Corps Medal with a citation for “extremely heroic conduct.” What convinced Powers was witnessing Jack’s appearance before a group of Gold Star Mothers, those women who’d lost sons fighting in the war. “I think I know how you feel,” he told them, “because my mother is a Gold Star Mother, too.” When Powers heard Kennedy say that and saw the reaction, he signed on and never would stop working for his new boss.
What Jack Kennedy brought to the table, besides his sterling war record and those well-known Boston names—Kennedy and Fitzgerald—was his obvious affection for the old Irish world he now was entering. He loved hearing his grandfather’s stories, from “Honey Fitz” himself, the city’s long-ago mayor and congressman.
Not surprisingly, the daily slog of introducing himself to constituents was not quite compatible with a chronic back problem, not when it meant going up and down the stairs of multifamily houses day after day. Come early afternoon, Jack would take a nap, then continue the trudge of one-on-one campaigning on into the night. He did this for months, and not everyone liked to see him doing it. The local politicians viewed him for what he was, a carpetbagger.
His voting address, after all, was a hotel, and he’d registered just in time to vote in the primary. Tom O’Neill, a local state assemblyman known as “Tip,” wasn’t impressed by the newcomer, war record or not. He was backing Mike Neville, the former Cambridge mayor, and the one whose turn it now was to hold the seat. “I couldn’t believe this skinny, pasty-faced kid was a candidate for anything.” He recalled the first time he met Kennedy outside the Bellevue Hotel: “He was twenty-eight but looked younger, and he still hadn’t fully recovered from his war injuries. He also looked as if he had come down with malaria.”
Tip’s description tallies with that of other observers. To Billy Sutton, he “wasn’t looking healthy then.” To Mark Dalton, the young attorney who would become Kennedy’s formal campaign manager, he resembled that same “skeleton” to which we’ve often heard him compared. His father, too, worried about his son’s emaciation. “My father thought I was hopeless.” Why? “At the time I weighed about 120 pounds.”
Chuck Spalding suggested that Jack’s precarious health, and his determination to surmount it at any cost, only added to the campaign’s wild, even hectic, pace. “This impatience that he passed on to others . . . made everybody around him feel quicker.” The trouble was, it didn’t necessarily make for great organization.
One out-of-the-blue crisis almost derailed Jack’s first run for office before it even officially had started. It seems that while he was obsessively wearing himself out walking the neighborhoods, he’d somehow overlooked a giant detail. The one to discover it was his old navy pal Red Fay, who’d come east to help out, he said, “even though I was a Republican.” Arriving in Cambridge, Fay found the headquarters a shambles of unpaid bills and invitations to speak, and was soon put in charge of trying to run the campaign on a more “businesslike basis.”
One of the campaign workers casually asked Fay about the candidate’s filing of his nomination papers. The deadline was that very afternoon, and yet no one had thought to do it. Not only that, it was now after five o’clock, and thus, past the deadline. So there they were, with Kennedy’s petitions not in, and the Boston Globe’s late edition already reporting the fact. Yet, incredible as it seems, given today’s 24/7 news cycle and minute-by-minute reaction speeds, no one was besieging the headquarters. Or even paying any attention.
“My God,” Kennedy said when he heard the bad news. It was 6:30 in the evening. “A series of frantic phone calls were made,” Fay reports. “Then, very quietly, the candidate and some loyal public retainers went down, opened up the proper office and filed the papers. Another couple of hours, and all the thousands of hours of work by the candidate and his supporters would have been completely wasted.”
This is a loyalist’s account of an after-hours escapade that had to have been blatantly illegal. But what’s remarkable is that Jack himself went into the municipal building that night and did what had to be done, putting those petitions in the right pile as if they’d been there by the deadline.
Kennedy pulled off other escapades. Early in the race, a rival candidate, Joe Russo, had run this newspaper ad: “Congress Seat for Sale. No Experience Necessary. Applicant Must Live in New York or Florida. Only Millionaires Need Apply.” The Kennedy campaign didn’t get mad, it got even.
Locating another Joe Russo, they paid him a few bucks to file as a candidate. The effect would be to confuse voters and skim off some of the politician Joe Russo’s votes. There was an Italian vote in the district and, this way, it would be divided.
But there were other sources of resentment. A popular newspaper column authored by a “Dante O’Shaughnessy” mocked Kennedy for being “oh, so British” and for having a valet who looked after him. Tip O’Neill recalled a far more daunting, more relevant advantage. Joe Kennedy had gotten Reader’s Digest to publish a condensed version of the John Hersey PT 109 piece that had run in the New Yorker, and now the campaign was mailing out 100,000 copies of it to voters. Tip couldn’t even remember a candidate before Jack Kennedy who’d had the money to pay for first-class postage.
What you did was rely on campaign workers to deliver literature.
And, even more astoundingly, Joe Kennedy, who’d made money owning chains of movie houses, had gotten local theaters to show a special newsreel recounting the story of Jack’s wartime heroism. No Boston pol, or voter, had ever before seen the like in a local congressional race. Or any race, for that matter.
An important—and brilliant—clincher came just days before the primary: Jack’s father and mother hosted a tony afternoon reception, a formal tea party, at the Hotel Commander in Cambridge. Women from throughout the district were invited, and all were flattered and thrilled. They’d always read about such fancy society events in the papers, but neither they nor anyone they knew had ever been to one.
Kennedy was starting to create what Tip O’Neill called the “Kennedy Party,” one separate from the regular Democratic organizations. He was making it happen by asking citizens who’d never been involved before to come on board. He, the millionaire’s son, was seeking the help of regular folk, not just the predictable party faithful or the machine hacks. Anyone stopping by Kennedy’s storefront headquarters would be asked to volunteer, and, in agreeing, they’d become, on the spot, “Kennedy” people. Thus, as word began to get around that someone’s son or niece was “working for young Jack Kennedy,” the popular appeal of the campaign grew, along with its strength.
Meanwhile, Jack himself continued acting in a way that was deeply impressive for someone of his wealth and name. He was out there going door to door on foot, and it was not simply a choice but rather a necessity. While his rivals could count on their associations with other politicians to further their candidacies, he was a newcomer who, despite his hard-core Boston bloodlines, didn’t have those established connections. His only means of getting to know voters was to meet them himself.
With either Billy Sutton or Dave Powers by his side, he went everywhere. “He met city workers, he met letter carriers, cabbies, waitresses, and dock workers,” Billy recalled. “He was probably the first of the pols around here to go into the firehouses, police stations, post offices, and saloons and poolrooms, as well as the homes, and it was probably the first Jack ever knew that the gas stove and the toilet could be in the same room.” Having the gabby, comical Sutton—a gifted mimic of character high and low—with him provided great company.
He deliberately made the rounds of the Cambridge city council
men, putting up with their silent responses or sometimes outright abuse. He was showing that he had the guts to do it, gaining respect, if not for this election, for the next time. He was honoring the political rule of keeping his enemies in front of him, showing them he wasn’t afraid and letting them know he had what it took to look them in the face.
At one candidates’ event, he listened patiently to each of his rivals describe their difficult lives. When his turn arrived, he, son of one of the world’s richest men, stood up and began, “I guess I’m the only one here who didn’t come up the hard way.”
He also did something else other candidates failed to think of, or were unable to imagine themselves doing, which was making a direct appeal to women. “Womanpower,” he would tell Tip, “the untapped resource.”
Red Fay reported that visiting junior colleges in the area with Jack back then was like traveling with the young, also very skinny Frank Sinatra. “They would scream and holler and touch him—absolutely, in 1946. I mean these girls were just crazy about him.”
Finally, there was the undeniable stamina Kennedy poured into the race, working hard at it until the very last day. Years later he would say it was mostly a matter of getting started early. “My chief opponents . . . followed the old practice of not starting until two months before the election. By then I was way ahead of them. I believe most aspirants for public office start much too late. When you think of the money that Coca-Cola and Lucky Strike put into advertising day after day though they have well-known brand names, you can realize how difficult it is to become an identifiable political figure. The idea that people can get to know you well enough to support you in two months or three months is wholly wrong. Most of us do not follow politics and politicians. We become interested only around election time. . . . In my opinion the principle for winning a war fight or a Congressional fight is really the same as winning a presidential fight. And the most important ingredient is a willingness to submit yourself to long, long, long labor.”
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