AS KENNY WOULD recall later, “1957 was one of the happiest years. It was the lead-up to ’58 and the huge reelection victory that secured his run in ’60; it was the year Jack won the Pulitzer Prize for Profiles in Courage, edged out Estes Kefauver for a seat on the Foreign Relations Committee, which he enjoyed on several levels, but most importantly, [it] was the year his first child, his beloved daughter Caroline, was born.”
“Never,” Kenny said, “had I seen someone so thrilled to be a father.” After Jack’s health scare, marriage difficulties, and Jackie’s two difficult and unsuccessful pregnancies and the loss of a stillborn child in 1956, it all seemed to turn around in ’57. They moved out of the large estate at Hickory Hill with its pristine, sadly empty nursery.
“The house had seemed,” Kenny said, “to bring them no luck. Jackie was miserable, and Jack had been driven to distraction by the morning and evening commuter traffic.” It was a house built for a growing family and children. The empty bedrooms seemed in some manner to mock Jackie, so they sold it to Bobby and his growing brood, with child six, Michael LeMoyne, to be born in 1957. They chose a Federalist townhouse in Georgetown on N Street. “When Caroline was three weeks old, they moved into their new home on N Street. Jackie, their new daughter, and Jack were finally, as Dave said to Kenny, on the surface at least, happy and at peace.”
Kenny was pleased. If there was more going on in the background, Kenny was unaware of it, as his relationship with the family, at least for now, remained need-to-know, though that would change as they approached the White House campaign.
For Kenny the next step was a return to Massachusetts and working with O’Brien to run Jack’s reelection campaign. The 1958 Senate campaign marked several significant firsts for the presumptive chief of Jack’s Irish Brotherhood. The race would mark a permanent and positive change of roles for Kenny O’Donnell. “You must understand,” Kenny told Sandy Vanocur some years later, “the 1958 race was critical and indeed crucial as the precursor to the 1960 national election campaign. This was also the first campaign when I began to fully assume my role as the future president’s right-hand man.”
Kenny would find himself exactly where he wanted to be and in a position for which he was uniquely suited. His new job as an advisor to Jack would keep him working in tandem with O’Brien, but it would also enhance his position in relation to the senator. This new role would also mark a change in the relationship between Bobby and Kenny.
The plan for ’58, as Kenny and Larry had originally worked it out, was for Ted Reardon, who had been Jack Kennedy’s long-serving (some might say long-suffering) aide and scheduler, to move from the office into a full-time role as Jack Kennedy’s personal and political assistant. This meant traveling with him at all times and being his political eyes and ears.
Kenny and Larry wanted to stay close to the ground and to the campaign operations in Boston. In many ways, they saw Reardon’s role as a reward for his long service to Kennedy. He, like Dave Powers, had been with Jack since that first campaign in 1946.
But Ted Reardon performed this new job for a couple of days before complaining to Kenny that he simply hated it. He was much happier working in the senator’s office. “Thanks, but no thanks. It was just too stressful,” Ted had said.
Surprised and without any other suitable candidate, Larry and Kenny decided that they would take turns until they found someone who could assume the role full-time. Neither Kenny nor Larry had envisioned the position for themselves. Kenny felt sure that Larry would be a natural for the role and ideally suited for such close quarters with Jack.
That did not work out so well, either. Jack was miserable. He called Kenny at his hotel in Boston early one morning, asking him to meet with him at his apartment at 122 Bowdoin Street. Jack made clear to Kenny that the job was his. Period. Kenny never asked O’Brien what happened, but Kenny never relinquished that job with Jack until fate intervened. In retrospect, one can only imagine how different the outcome might have been had Reardon or O’Brien wished to stay.
In many ways, while Kenny and Larry loved Reardon, as did Dave Powers, they began to realize in hindsight that it was a good thing he had turned the job down. He was not well suited for the new role. As Jack’s political hunger and ambition grew, the role increasingly required someone who was not only sensitive to political realities as they arose but also adept in political operations beyond the Senate campaign.
The role also required a fearless “don’t give a damn what people think” quality and an ability to stand up to the senator and the Kennedy family no matter what that Kenny seemed, for better or worse, to possess. In addition, Jack required someone in whom he had absolute trust, but also someone who had no fear of Jack. In other words, someone who could shoot straight with Jack, without fear of reprisal or retribution. Kenny fit the bill perfectly.
Kenny and Jack shared, from the beginning, a mutual respect founded in their war experience and their common distaste for sentimentality.
“Kenny was a guy’s guy,” said his old friend William “Bill” Connors, “who came right at you. No holds barred. You knew where you stood with Kenny, like it or not.”
Jack was the same sort of man, so the two seemed beautifully suited to work together, spending long hours on the political hustings under enormous pressures without, importantly, driving each other nuts.
Kenny also kept his mouth shut. Any conversations he and Jack had stayed between them. That was another quality Jack would come to absolutely appreciate.
“Kenny,” another pal noted, “also was a political guy, so it allowed Jack to be the candidate and Kenny to cover the political angle, then transmit that information to O’Brien, Bobby, or the father, whomever needed to know in order to act.” The truth was a lot simpler than all that because Jack had begun to trust Kenny’s instincts and was comfortable around him. In the end, that was all that mattered.
Some found Kenny’s approach intimidating, but he had just the persona Jack needed. He also seemed to have no personal ego and couldn’t care less about anyone else’s opinion, with the exception of Jack.
“Kenny,” Vanocur recalled with a chuckle, “didn’t give a damn who liked him or who didn’t. He was his own man. Always. I’d never seen anything like it in politics.”
Kenny took great pains to ensure his independence. As he explained later, “It is important to understand that during this entire period, from my first involvement with Jack Kennedy right through the ’58 campaign, I was never a paid staffer. I never wanted to work for the Kennedys, and by that I mean get a paycheck. I felt it would change the relationship. Helen was in complete agreement with me from the very beginning. It gave me the ability to speak my mind with Jack Kennedy. I know it made me more comfortable. I know he appreciated it, and it made him more comfortable. He knew he could speak his mind with me with no fear. I actually did not start getting paid for my work with Jack Kennedy specifically until the White House, and that would be January 1961, after the inauguration. At that point, it was more than appropriate. We were both comfortable then, because in truth, I was being paid by the American public, not President Kennedy.”
The decision not to be paid put Kenny in a unique and powerful position within the Kennedy organization. It brought him deeply into their inner circle and garnered a respect from them that no staffer would ever attain. Joe Kennedy, who had been suspicious of Kenny from the beginning, was impressed.
This tough decision must have placed burdens on Kenny’s home life. But Jack never wondered about Kenny’s real or imagined agenda. Kenny never worried that telling it like it was might get him fired. This sense of freedom in their relationship cemented an honesty and trust that would only build in the years to come as they spent increasing amounts of time together. Jack, who was not given to trust easily, came, by the end his life, to trust Kenny utterly and completely.
Jack later said, “I never doubt Kenny. His loyalty to me is absolute. I trust him completely. We may disagree at times over politics or people. He is not always right, nor am I. But I always know he has my back and always will. He always calls it like he sees it. I appreciate that.”
This faith Jack placed in Kenny led to another unofficial title for Kenny. The press would dub him “the ultimate insider.” You knew, said one Washington reporter, “when Kenny spoke . . . he spoke for Jack. You could take it to the bank. He never lied or misled. He always played it straight with us, whether it was answering a question or telling us to go to hell. We respected that.” His agenda was Jack’s agenda.
Kenny and Larry’s strategy for the 1958 Senate race was a simple one: use the Kennedy machine to scour every corner of Massachusetts for a vote. The goal was to run Jack as if this race were in question and everything depended on each vote. They had to get the vote out and build up the vote count. This was not an easy task in an off-year election against a particularly weak, nonpolarizing opponent, Vincent J. Celeste. Celeste was a Republican whom Jack had faced in the House in 1950 and had already beaten once. Later, Celeste would correctly point out that Joe’s money made a serious bid by any candidate against Jack difficult. While that was certainly true, Kenny and Larry believed that the sheer number of registered Democrats in the state who were inclined to back Jack against any Republican was another key element in Jack’s success.
Kenny and Larry, having taken over the Massachusetts state party, had spent the time between Jack’s election and the ’58 race making sure Jack’s reelection was as preordained as possible. They intended to establish a sense of inevitability to Jack’s reelection, while at the same time working to keep Jack’s involvement to an absolute minimum. Nevertheless, they worked tirelessly to give the voters the impression that Jack’s presence was everywhere in their state.
The Irish Brotherhood could hardly have kept their political operation humming across Massachusetts without the healthy budget afforded to them by what Kenny referred to as “the Old Man’s purse strings.” In the end, Kenny noted that Joe spent something in the neighborhood of $1.5 million on Jack’s reelection campaign. Such an amount of money, in 1958 dollars, was unheard of for a race not in question.
Such expenditures in grassroots organizing, advertising, and overhead allowed Larry and Kenny the resources they needed to build the Kennedy machine and put it into operation as they had long envisioned it. This time, however, they did so with an understanding between Joe, Jack, and the Brotherhood that the Kennedy machine was being well oiled with Joe’s cash in preparation for running it nationwide.
This was about a lot more than Massachusetts. Their goal of a landslide victory for Jack, once achieved, cemented his position nationally and placed him exactly where they had hoped it would: on the radar screen of the national media.
Kenny and Larry also made sure that at every opportunity the media, both print and fledgling television, were in tow. They wanted to expose Jack as much as possible on the national stage, not only to convince national party leaders of his viability. It was also to expose the nationwide audience to this young, handsome candidate with a beautiful wife and child. This exposure was accompanied by design with a sense of inevitability and Hollywood-style glamour that had not been seen before in national politics.
Kenny had just seen the effect that the Kennedy panache had on the crowds in Chicago in ’56 as Jack gave his concession speech, which turned into, in many ways, an eventual victory speech for Jack. Kenny and Larry were in full agreement here with Joe Kennedy, that getting Jack and Jackie out there in the public eye, not just in Massachusetts but nationally, was of critical importance. They approached every media outlet they could think of. The strategy worked in the end, but not without a few funny slipups.
At one stage of the campaign, Rowland Evans, a reporter from Time magazine, and two other reporters were all doing profiles of Jack. Evans’s piece was for the cover of Time, thus his traveling with the candidate had taken on a special importance. The public relations value of a Time magazine cover was not to be underestimated.
Because Kenny and Larry had sought to keep Jack’s physical role and involvement in the campaign to a minimum, whenever they did have him, the schedule was jam-packed, with no room for error. For the most part, all went according to plan. But not always.
One particular campaign stop, Kenny recalled later, involved a trip to Quincy, Massachusetts. Kenny had personally made the choice for Quincy, feeling it would showcase what he and Larry later jokingly called the “vaunted Kennedy machine in action.” The trip actually would teach Jack, Kenny, and Larry that they still had much to learn before they were ready to take this show national.
From the moment they arrived, everything went wrong. For some reason the Kennedy secretary, Jack Curley, a young, efficient lawyer and vet who exemplified the new wave of Kennedy recruits, had gotten it into his head that they were arriving at 10:00 a.m., but instead the candidate and his entourage arrived at 9:00 a.m., an hour early. When they arrived, media in tow, there was no Kennedy secretary to meet them. There was only confusion.
Kenny’s main concern was that the savvy and experienced Evans from Time was there along with a reporter from The New York Times and a few people from the Boston press. The last thing they wanted was some headline written in a national publication saying, as Kenny imagined it, “‘This is amateur hour and Kennedy has the most confused, screwed-up campaign organization on the planet.’ Not a good piece as you prepare to run nationally.”
Evans had only the one day, so whatever impressions he took away from this day’s events would comprise the entire story.
But Kenny and Jack improvised quickly with a tour of the Quincy shipyard, much to the surprise of the superintendent who ran it. Once they knew they were in trouble, Kenny sprinted ahead, getting to the shipyard and explaining their dilemma. The fellow, eager to please the senator, wanted to help, but it was Saturday, and there were at best only one hundred men around. Not to be deterred, Kenny suggested that the senator could inspect a ship. When the entourage arrived, Jack shot a nervous look toward Kenny, who walked quickly up to Jack announcing, “Senator, this is the ship you were to inspect.”
“That’s right, Kenny,” Jack replied, no doubt with great relief. “We are going to inspect a ship here.”
With that, Jack, with Kenny in tow and the press clipping at his heels, inspected the ship from bow to stern. After this, and still with no Kennedy secretary in sight, the group quickly headed to the local mall, where Jack and Kenny leaped out of the car, showing Jack’s “grace and vigor,” as Kenny recalled it, laughing. The reporters were impressed with how rapidly Jack moved through the mall, shaking every hand, even climbing over barricades to greet people with his familiar Boston accent: “Hi, I am Jack Kennedy!”
Kenny and Dave Powers chuckled afterward. Kenny said, “If only the press had known that we were moving so fast because the day was a complete disaster, the schedule was blown to smithereens, and we were making it up as we went along!”
Kenny recalled that much of the day went like that, racing with Dave from made-up event to made-up event, “hoping that we would not get found out.”
Later that night, when Kenny joined the reporters for drinks at the pub, not far from Jack’s Boston apartment, “the press marveled at how terrific the senator was on his feet, how healthy he appeared to be, which was not what they had heard, and how organized our operation was.”
One reporter even noted, “You have days like this on the national campaign, you’re headed to the White House! What a terrific operation!”
Kenny said that he and Dave exchanged a glance and downed their beers as fast as possible. Later, when Kenny rejoined Jack back at the apartment, he filled him in on the unofficial reviews of the press corps.
“He shot me a look,” Kenny said. “‘Next time,’ he asked, ‘should I plan my own schedule and advance myself? It seems you and O’Brien have a bit too much on your plate to make sure this campaign runs well. I would not want to overburden you.’”
The point, while made in jest, was clear. Don’t screw up again. And if you do, try not to do it with the national press in tow.
It was during this critical 1958 campaign that Jack discovered perhaps his best-kept secret political weapon in Jackie Kennedy. Kenny had seen little of Jackie since Helen’s party for her at the Parker House in Boston and the wedding in Newport. When Helen would ask him about some article or puff piece on Jack and Jackie or the birth of their daughter, Kenny would glaze over or run for the door.
Kenny liked Jackie well enough. She seemed fine as far he knew. She just didn’t talk politics, and so Kenny had no need to spend a lot time chatting with her on the rare occasions when their paths crossed. He would not have known what to talk to her about anyway. Kenny was comfortable with someone like Helen: charming and attractive but also able to talk Harvard football and poll results in Ward 6 in Boston, and able to throw a hell of a good pass just in time to beat Bobby and Ethel during a game of pick-up at Hyannis Port.
Jackie, as Kenny was about to find out, was an entirely different creature. Like Kenny, she did not give a damn what other people thought of her or her actions. She did what she wanted, a trait that both Jack and Kenny would alternately admire and, especially during the White House years, find maddening.
“The president,” Kenny said, “would ask Jackie to do such and such, which she did not want to do. She’d ‘yes’ him to death, then do exactly what she wanted. It drove him crazy at times, but Jackie was always her own person. Always.”
What Kenny had heard about Jackie was not necessarily encouraging. He knew secondhand from staffers in Jack’s office and some political wives that she was “a difficult girl and sort of a snob,” that she, in fact, did not like politics and did not even like Jack Kennedy being in politics. Kenny remembered hearing all this in the background, but he couldn’t have cared less. It had nothing to do with him or his role in Jack’s political career.
This was all in Kenny’s mind early one morning when Jack told him over one of Dave’s wonderfully cooked breakfasts at the 122 Bowdoin Street apartment, with some mischievous delight, waiting to see Kenny’s reaction, “Jackie wants to campaign with us. She is going to join us on the swing through Haverhill. This will be her first, and I want you to show her the ropes.”
Kenny was horrified. “She’s a woman,” was all he could think to say.
Jack stared at him, no doubt enjoying Kenny’s discomfort, and said, “Nothing gets past you.”
Jack was clear: the next day Jackie would be joining them. Kenny knew when he’d lost the argument. That night he went home and promptly called Helen at their new house in Bethesda, just outside of Washington, to complain. He didn’t know what to do with a woman, he said to her. Helen, surveying her home, which was by then filled to the brim with four children, quipped that he seemed to have figured it out fairly well in the past. Kenny was not amused.
“I’ve been told,” he complained to Helen, “she’s difficult.”
“By whom?” Helen demanded.
Kenny said that Joe Kennedy had called him that very afternoon and said she was “a difficult, fragile china doll who might not be excited about shaking hands with Vernon Clearly of Taunton.” Helen laughed. “This is the same Joe Kennedy whom you ignore 90 percent of the time, but this time he’s got to be right.” Kenny felt that Helen simply was not appreciating his plight, so he forged on.
If that was not bad enough, Bobby called Kenny to ask him to please “try to have some manners. I mean you really should try to have some manners and be nice; she’s very fragile. You don’t want to frighten her. She’s never dealt with anybody like you,” Bobby said worriedly.
“I’ve never dealt with a woman like that,” Kenny protested to Helen. “What does that mean, ‘Have some manners and don’t frighten her’?”
Helen laughed. “Maybe your brother Cleo will pinch-hit for you,” she replied, completely unsympathetic and obviously enjoying his discomfort.
Kenny was horrified. He had no idea how he was going to handle such a situation. Hardball politics with the Dever people he could deal with; toughing it out in Chicago with Kefauver’s fellows, that was okay; tossing a guy through a window or over a bar, that was fine. But how the hell do you talk to a china doll?
Before they hit the trail the following day, just as they climbed into the car outside the Kennedy apartment on Bowdoin Street, Jack pulled Kenny aside, whispering so that Jackie would not overhear them. “Jackie doesn’t like campaigning, and she doesn’t like politics or politicians. You have to be careful with her. She is a rather delicate flower.”
Kenny couldn’t take this anymore. “A delicate flower?! Jesus!” was all he could think of. “Does she know what you do for a living?” Kenny asked, half to himself.
Jack shot him a dirty look. As they climbed into the car, Kenny thought to himself, The McClellan Committee doesn’t look so bad just now. Maybe he should have stayed in Washington with Bobby!
Later, after Jackie and Kenny became close and formed a deep and trusting friendship that lasted for years after Jack’s death, they would laugh about this first substantial meeting.
“Massachusetts politics constitute a rather rough variety of politics,” Kenny recalled. “I felt when Jack told me this about her that in fact this was not going to go very well. We had a day trip scheduled, and particularly during a trip like this, you never know what you are going to run into. So I was very concerned about how to handle Jackie. I wanted her to be happy and content. I wanted it to be a good day. My main concern was I did not want her to fall apart, start crying, and cause any trouble for the candidate. I would not have known what to do with a sobbing, hysterical woman.”
“I was astonished when I met her,” Kenny laughed later. “Larry and I were prepared for a very high-strung, fragile, demanding china doll who couldn’t cope with anything. This is what the buildup had been. We did not know what the hell to expect. Well, I recall the day vividly because she was the most pleasant, sweet, beautiful, elegant child, and very funny. I found her to be that way from that point forward. She was and is simply a delight as a person. She never raised her voice. She never once complained. She was not enthusiastic, but she never complained. In truth, most politicians’ wives are not excited about this aspect of their lives, either, but most are phony and put on a big show. She never did that. She did exactly what you asked of her, but she was never a faker about it. She was not terribly interested in meeting the local politicians, whose big excitement was describing their local shoe factory. It wasn’t that unusual to not want to listen to some of those fellows. Half the time, I didn’t want to listen to them, either. I admired the fact that she wasn’t a phony. I noticed that the locals also seemed to admire the fact that she was not a faker. She was beautiful. Beautiful in a sense that these fellows were not accustomed to seeing. Jackie was very elegant and classy. Unusual, not your regular politician’s wife, but then Jack Kennedy was no average politician. She would travel with Jack, and he would introduce her. She would say a few words and knock everyone dead. All she had to do was say hello, and these average fellows were captivated. It really was a foreshadowing of the future. This was before she had become completely transformed, but you could see that it was coming.”
“Over drinks a few days later, I asked the senator, ‘Have you actually met Mrs. Kennedy?’ He looked at me astonished and asked what I meant. I told him of our experiences, and I said, ‘Senator, she is anything but fragile; she’s smart as hell, capable, funny, and has a keen political instinct that in certain situations was better than ours. But fragile flower? No.’” Jack nodded, but Kenny sensed that he was surprised. Jack was beginning to understand that if he could persuade her, Jackie could be a useful asset on the campaign trail.
There is one trip in particular that Kenny recalled as marking the beginning of their relationship, or the start of Madame La Femme, as Kenny had dubbed Jackie.
This was a standard political trip for the Kennedy operation to Western Massachusetts’s industrial towns. This trip would be different, however, because it marked their first political trip with Jackie. And because it was her debut, Jack in particular was, as Kenny put it, “a wreck.” Kenny and Larry wanted her to be happy, mostly because they wanted her husband to be happy.
“We were all very hungry,” Kenny recalled, “so we stopped finally for lunch. One of the things that we did during the campaign was we always took two hours for lunch. We did this throughout Jack’s career. This was one of the things that we always paid great attention to and made sure to take a full two hours. It was very important for Jack’s health.
“We really held our Kennedy secretaries throughout the state to this routine. It would also later be an important part of our national schedule. We did it in the 1960 campaign, and we were very tough with everyone about it. Joe Kennedy was the one who first spoke to me about it. He asked me directly for this one concession and said for his son’s health it is important that he eat properly. It was one of the only concessions I made to Mr. Kennedy. I will say I did so with great pleasure, though, because I felt he was quite right.”
Kenny still was not fully versed in Jack’s health issues, but the recent health scare in 1955 had given him enough information to know the well was far deeper than it appeared.
Kenny could see that Jackie was laughing generally at the entire operation. She was not quite able to figure out what all these maneuvers were about. She didn’t know any of the players or understand the purpose of it all. It was evident that she thought it was all a bit silly.
“We were in the back room in a restaurant. John Lenihan was there. He was our secretary in Haverhill. We were all seated around this table, having our lunch: steak, baked potato, glass of milk, and chocolate cake for dessert. That was really our standard lunch, always prearranged in advance, so we could just sit down and order it. Jackie was terribly amused that we all ate the same thing every day. But it was what the senator wanted, and so that was that.
“Senator Kennedy was giving me his usual twenty-five instructions: ‘I want you call so-and-so. Then call that SOB down there and tell him to do such-and-such. Call this fellow over there and tell him to do this.’ I had my pencil and my usual notebook, which was really the back of an envelope. I wrote down every single thing he said and made a list.
“Jackie was eating, sipping her drink, and watching me intensely. We got all through the list, and Jackie said, ‘I have always wondered what exactly is it you do with all those things Jack tells you. You keep writing them all down, but I have never actually seen you do anything with any of the items on the list.’
“Senator Kennedy had decided, since Jackie was with us, to relax a bit, and so he had ordered everyone at the table a glass of wine with lunch. I thought it was quite funny that she should notice this, and I said to her, ‘Well, you know what I do with them? I wait until he calms down, and then I only do what I think is important, and I throw the envelope out.’ Jackie burst out laughing.
“‘I knew that!’ she declared. ‘I just guessed.’
“Jack was less than amused. While he likely understood my routine better than most, he was as nervous as a schoolboy and obviously was trying to impress his wife.
“He was furious. ‘You son of bitch,’ he barked, ‘I bet that is just what you do!’” Kenny tried not to laugh, suddenly realizing for some odd reason that Jack was really trying to impress Jackie.
“Oh, Jack,” Jackie said, putting her hand on his arm to calm him down. “He’s just teasing you. Relax. It’s all supposed to be good fun.”
Kenny watched as Jack immediately returned to his good-natured, teasing self and laughed.
“You SOB,” he said again to Kenny as they rose to leave. “I have no doubt that you do exactly what you want, no matter what I say.”
Kenny laughed, lagging behind as they left the restaurant to return to their cars. He caught Jackie watching him and pretended to throw the envelope away. He laughed instead, stuffing it in his suit coat pocket. It was the first time Kenny had been exposed to Jackie’s charming side, and Kenny was utterly captivated.
Kenny told Vanocur later, “She had not yet made the full transformation into this enormously popular national figure, but you could see the potential was there. For the first time, I also saw just how important she was to the senator. Her good humor and wonderful perspective kept him level-headed, and in politics that is critical for a candidate.”
It was clear to the Irish Brotherhood that Jackie was a political asset. Kenny took note of it for the future, though this was not something he needed to write down on an envelope.
The campaign that Kenny and Larry designed was, as Kenny described it, “as nearly perfect in planning and operation as an election campaign in an off year could be.”
AS THE CAMPAIGN got under way, the first order of business for Kenny and Larry was to bring together the Kennedy secretaries from throughout Massachusetts. This would, in essence, be a copy of the 1952 race, but with clearer footing and more political cards in their deck, Kenny and Larry were determined to run up the numbers. They instituted the same card system they had in 1952, bringing in the girls, led by Helen Lempart and Kenny’s younger sister Justine O’Donnell, to update the system; this also meant pushing the Kennedy secretaries hard. While money wouldn’t be an issue, access to the candidate this time round would be extremely limited, so Kenny made clear that days were to be jam-packed and that each event needed to bring in the votes as well as pound home the Kennedy sense of inevitability.
“The truth was,” Kenny and Dave recalled, “While [Jack] was running for reelection as senator for Massachusetts, Kennedy was still carrying on his national campaign for the 1960 presidential nomination, making appearances at political gatherings all over the nation. This meant the time he could give to personal campaigning in Massachusetts was limited. Actually, he spent only seventeen days in the state between the September primary and the November election.”
Kenny told Vanocur, “He and O’Brien had worked out the schedule for the senator from September to November during the lull in campaign in the summer months. Jack, Jackie, and Caroline had been in Europe, ostensibly on a tour for the Senate Foreign Relations Committee. He was due to return on a ship that would dock in New York on primary day in Massachusetts; both Kennedy and Furcolo were running unopposed on the Democratic ticket. “The schedule was so tough that Kenny admitted later that he dreaded showing it to the senator. They had already given it to Joe, who had joined them at the dock to greet his son. Upon reading it Joe exploded. “What are you trying to do, kill him?!” he roared.
Kenny had shrugged. “Given the limited time we have with him and the numbers we need to run up, it is what we have to do.”
When Jack and Jackie got off the boat, he took the schedule from Kenny, and with that computer-like mind of his, he looked it over immediately. Handing it back to Kenny, all he said was, “Looks good.”
Joe was appalled, but Jack and Kenny were more worried about the primary vote that day. While such a vote was always light in off-year elections, Furcolo was far ahead of Kennedy in the totals and that was not good, particularly in the Italian districts.
There was also some anger among teamsters, longshoremen, and other labor unions over the Saint Lawrence Seaway and Bobby’s role at the McClellan Committee; since Kennedy was running unopposed, they decided to blank the ballots, “which,” Kenny said, “substantially dropped our numbers.” The light turnout and disappointing numbers in the primary made it easier to get Jack to agree to the schedule, and while both Kenny and Larry well knew that a light primary does not necessarily mean anything for November, they were still disgruntled and concerned. These were not impressive numbers for a candidate rumored to be running for the White House in 1960.
“We cannot,” Larry said, “take any chances. It must be an all-out press.” And so it would become.
The ’58 campaign would “follow really a small-scale model of what we did nationwide in 1960 and had one attractive feature that was unfortunately lacking in the later presidential campaign: We had Jackie Kennedy, who was able to accompany her husband on several of his long days’ journeys. Local politicians went nuts over her,” Kenny said. “Trust me, there are lots of homes around Massachusetts with pictures of Jackie taken during the ’58 campaign. It was but a small inkling of what would happen in the White House.”
By now Kenny had gotten used to Jackie and her style. He was quickly learning firsthand what a powerful political weapon she could become. Jackie, Kenny believed, had been key to their success in 1958. He would come to very much regret that she would not participate in ’60, which is why her agreement to help in the ’64 campaign had been a source of such excitement. But, still, Kenny and Jackie’s early meetings in ’58 were not without their bumps in the road.
If Kenny called Jackie Madame La Femme privately, she called him “the wolfhound”—for his serious demeanor, intimidating style, and fierce protectiveness of Jack. The nickname also referred to the fact that every time Kenny arrived, Jack had to return to work.
But, from the 1958 campaign forward, Kenny and Jackie would learn to dance around the political realm, both knowing that in their own way they had Jack’s best interests at heart. For instance, Kenny and Jackie often joked later about another humorous incident from the ’58 campaign.
Kenny and Larry had been sent to Haverhill, Massachusetts, with Jackie in tow. The community was largely French, with many members still speaking French. Both Kenny and Larry believed, correctly as it turned out, that Jack would carry the area by overwhelming numbers. They also felt that Jacqueline Bouvier Kennedy would be a smash hit!
The schedule called for a tea at the local church parish’s school hall. Unfortunately for Kenny and Larry, the local Kennedy secretary had gotten the day wrong. When Kenny and Larry arrived with Jackie, on what would be only their second trip with her and her first trip without Jack, there was no one there but a few nuns and the parish priest.
As they walked into the room, used mostly for recitals and practices for the schoolchildren, they were expecting a large crowd. Even though Kenny, Larry, and Jackie had arrived a day early, the kitchen staff at the church had made enormous urns of hot tea, surrounded by delicate white-and-pink teacups. To make matters worse, each of the tables was piled high with mouthwatering small tea cakes, carefully frosted to reflect the flags of the United States and French Canada. The pièce de résistance was the piano player, an older nun who had been long retired but who loved the Kennedy family and was brought back especially for this grand occasion.
The idea was for Jackie to meet and greet the enormous crowd that no doubt would soon arrive and then address them in French about the importance of supporting Jack’s candidacy for the Senate. Jackie immediately began chatting with the priests and the nuns while waiting for the crowd. She looked elegant in a classic navy cloth coat, gloves, and pillbox hat. Kenny watched admiringly as Larry watched the huge clock over the doorway tick away the time. Still no Kennedy secretary and no crowds.
Larry finally sidled over to Kenny. “It’s been a half hour; something is wrong.” Kenny, brought back from reverie, looked up at the clock. “Shit!” the wolfhound exclaimed loud enough for Jackie and the priests and the nuns to hear. The room remained mostly empty. Kenny realized he was going to have to improvise to avoid a disaster in front of Jackie.
Jackie shot Kenny a disapproving look. He shifted his weight uncomfortably and waved, turning to Larry, “Call the SOB!”
As Larry left to call, Kenny took action. Not knowing what else to do and wanting it to look like something was happening, Kenny ordered the nun to begin playing.
“Play what?” she asked, concerned.
“I don’t care! Anything,” the nonmusically inclined Kenny said. “‘Danny Boy’!”
The nun stared at Kenny, puzzled. “I hardly think that is appropriate for an afternoon tea,” she replied, looking at him sternly.
It reminded Kenny of his parish in Worcester. He didn’t like the look then and he did not appreciate it now, either.
“Play anything you want,” Kenny snapped as he suddenly began pouring tea into the cups and stuffing pastries in his pockets.
Just then, Larry returned, breathless. He stopped and watched Kenny, puzzled for a moment. “What are you doing?” he asked, almost afraid to get the answer.
“Start drinking some tea and stuff some of these pastries in your pockets, Kenny barked to Larry. “You as well,” he said to the sister, shoving a plate over to her at the piano.
Larry obliged at once. “And why are we doing this?” he ventured to ask as he began stuffing the cakes in his mouth.
“Jackie keeps looking over here, and she is trying to head this way. I want it to look like somebody’s been eating and drinking the tea.”
Larry surveyed the empty room, save for Jackie and about a dozen nuns. “Who exactly is she to think has been eating them?” Larry asked through a stuffed mouth.
Kenny looked up from his hands full of cakes. “Shit, here she comes.” Kenny heard a distinct disapproving hiss behind him.
“Sorry, Sister,” Larry said, spitting cake out as he spoke.
“Dance,” Kenny ordered.
“What?” Larry asked, incredulous.
“Dance,” Kenny ordered. “I will be right back.” Kenny began dancing across the room toward the door, cake in one hand, teacup in another, and sort of waved as he headed out the door. Jackie came to a full stop watching him, puzzled, amused, or perhaps frightened; it was hard to tell from her expression. She then turned to watch Larry, who waved while dancing clumsily from side to side and sipping tea. She looked past him toward the nun, who was dutifully playing while taking occasional breaks to stuff cake in her mouth.
Jackie stood elegantly but with the most puzzled expression on her face.
She admitted to Jack later that she really did not know if this was standard fare or perhaps the vaunted “wolfhound” and his partner in crime, O’Brien, were having a breakdown and perhaps she should call her husband?
Before she could decide, Kenny returned, still holding the cakes and teacups, followed by an older nun, who turned out to be the school principal, and a sea of giggling girls, not one of whom could vote. Also along was the gardener, and Kenny had managed to round up a few passersby, which included women with baby carriages.
As they all converged in the room en masse, the schoolgirls’ giggles and squeals at the sight of the food reaching an ear-splitting level, they all spied Jackie standing in the middle of the room. For a moment, all parties surveyed each other in silence. That is when, teacup in hand, Kenny began dancing with the principal, while Jackie watched in amusement. Then Kenny got to Larry and began to dance. The girls giggled, took this as sign, surged past this beautiful lady—with no idea who she was—and headed for the food!
Kenny and Larry kept dancing as Jackie approached them, hands clutched behind her back, purse in her hand. “Do you think she will hit us with it?” Larry asked as he two-stepped badly with Kenny.
Kenny watched her approach. “No, but I am dreading what she is going to tell her husband!
Larry was watching Jackie and said, “Stop leading, Kenny!”
Despite their best efforts to dance away from Jackie, who was a superb athlete, amateur ballet dancer, and horsewoman, Jackie solo-danced right up to them. Escape was impossible.
“The jig is up,” Kenny said.
“Thank God!” Larry said with relief. “You were stepping on my toes. I don’t how women do this!”
Kenny glared at Larry.
“Kenny,” Jackie inquired in her elegant, whispering voice.
“Yes, Mrs. Kennedy?” Kenny replied as if this were all perfectly normal. “Anything wrong?” he asked over the din of screaming schoolchildren.
“I don’t want to hurt your feelings,” she said, her deep brown eyes locking with his, “but shall we both save ourselves further pain and embarrassment and simply admit your event is a failure? Besides,” she said, looking at the two of them with their overstuffed pockets, cakes bulging out of each one, “I really don’t think either one of you could stuff another cake in your suit pockets or drink more tea. Shall I just take it from here?” she asked with a tone that said, Let me show you how it’s done.
Sheepishly, Kenny and Larry agreed. With that Jackie turned to go but stopped short and looked back. “Besides,” she added, “I really don’t think I could stand watching you stepping on Larry’s toes any further.”
Kenny grimaced.
“Follow me,” she ordered.
From there they followed her to the monsignor, who was trying in vain to corral the girls away from the cakes.
Jackie whispered something in French, and before they knew it, they were sitting in the monsignor’s private den in the rectory. Jackie requested a beer each for Kenny and Larry. She had a glass of wine with the priest as they spoke in French. Kenny had no idea what they said; he did not ask, but he could tell that the beer tasted good.
As they climbed back in the car later, Kenny said little. What could he say? She was obviously going to complain to her husband and there would be hell to pay.
Finally, after a painfully quiet trip they met Jack back in Boston at John Fox’s place for dinner. Dave had already ordered it: steak, baked potato, salad, and chocolate cake. As they entered the back room, Jack rose, pain briefly evident on his face, but it was quickly replaced with delight at the site of Jackie.
“How did it go?” he asked, excited, shooting Kenny and Larry, who’d hung back, an it better have gone well look.
After a pause as Jack pulled out a seat next to him for his wife, she smiled broadly and met Kenny’s steady gaze. “It was wonderful, Jack,” she exclaimed. “Just the most unique experience I’ve ever had. I also was exposed to Larry and Kenny’s hidden talents. They certainly have panache.”
Kenny smiled and in a rare moment pulled the waiter aside and ordered two beers.
“Thanks,” Larry said,
“Get your own,” Kenny said. “Those are for me.”
Jack, sensing something was up, looked to Kenny for an explanation. Kenny simply smiled and downed his beer. Jack let it go, but as dinner came to a close, Jackie again piped in, “Jack, darling,” she said with a smile at Kenny, “I don’t think Kenny or Larry need any cake. They’ve brought their own.” Jack looked over at Kenny, puzzled.
Kenny suddenly remembered all the cakes in their pockets, now stale and stuck together as he and Larry pulled them out of their pockets and put them on the table in front of them.
“For the kids,” Kenny said.
Jack looked at him skeptically. “You are going to mail the cakes to Washington?”
Powers, sensing pending disaster, not for the first time, quickly stepped in with one of his stories, changing the subject. “You can tell me what happened later,” Dave chuckled as they headed to the car.
It was days later, when sitting with Jack at lunch during a jam-packed critical campaign day, that Kenny got confirmation that Jack had heard the whole humorous and disastrous story.
As Jack was looking over the afternoon schedule and Kenny and Larry were diving into their steaks, Jack suddenly asked, “Larry, how are your feet doing?”
Larry looked up, puzzled for a moment. “Fine,” he said, confused.
Kenny stopped chewing and looked at Jack, waiting for the explosion, but instead he got an amused look.
“Good,” Jack said, “because I hear Kenny has two left feet.”
Nothing more was said until years later in the White House, when Jack humorously admitted to Kenny that Jackie had told him the entire story with great relish and spared no detail.
In the end, as it turned out, Jackie had convinced the monsignor to endorse Jack from the pulpit at every Mass and to do so in French.
As things turned out, Jack would carry the district overwhelmingly.
There were some changes to the ’58 campaign that Kenny and Larry did not like, but they were dictated by Joe. It seemed to Kenny anyway that it was the senator’s way of appeasing his father. For instance, rather than set up Kennedy for Senate headquarters across the state as they had in 1952, Jack decided they needed to work out of single headquarters on Tremont Street in downtown Boston. Kenny, whose entire focus was running up the numbers, was dismayed. In addition, this time around there was no Bobby. He was busy writing his book The Enemy Within, about his days at the McClellan Committee, and wrapping up the committee in preparation for 1960.
The 1958 campaign would be organized differently than the one in 1952. The role of campaign manager would fall to Jack and Bobby’s younger brother, Teddy Kennedy, who was, Dave said, “getting his baptism by fire,” and Steve Smith. Steve, a New Yorker, was newly married to their sister Jean Kennedy, and it was Steve who was really in charge of the day-to-day operation. He was new to the Kennedy organization and family for that matter, but Kenny and he immediately hit it off. Smith was low-key, sharp, and excellent with money and numbers. Kenny found him to be a no-bullshit kind of fellow on whom he could always rely to give him straightforward feedback and advice. It was the beginning of a relationship that would simply strengthen over the years.
“Steve is,” Kenny said, “smart as hell, great political insight and instincts, his own man, so I could approach him with issues regarding the senator and the family that I could not discuss with others. I knew whatever we discussed would go no further.”
Steve, Kenny learned, could always be trusted to keep any and all conversation private.
There was one particular incident that stood out for Jack Kennedy during ’58 on these jam-packed campaign days. Jack would make a point of moving into the crowd, shaking hands and talking to voters. After one seemingly successful event, where the crowds had roared and surged around Jack as they left a factory, Kenny noticed that Jack seemed troubled.
“What is it?” he asked, puzzled by why such a great crowd might leave the candidate troubled.
Jack stopped and winced for a moment in pain before climbing into the car. “Half those people,” he said, “were not registered to vote.”
Kenny stopped. He had not checked, just assumed. Jack put up his hand to indicate that that was not his point. His concern, a focus that he would take into the White House, was that all these nonregistered voters in essence had no voice in the democratic process. It bothered him deeply. As a war vet, who had fought for these cherished rights, it bothered him that given the opportunity, people would not choose to register and vote.
“It bothered him deeply,” Kenny said, “that there were millions of people, particularly in black populations, who could cheer a candidate but not vote for him.”
Jack tasked Kenny with refocusing the Democratic National Committee once they were in the White House. “At the time of his death,” Kenny recalled, “in the 1964 campaign he wanted the Democratic National Committee to have two main functions only: to raise as much money as possible, and to spend most of it on registering voters, particularly in poor and minority areas.” President Johnson would carry this policy forward, going as far as to appoint Kenny executive director of the Democratic National Committee, a job he took on in addition to his normal duties for President Johnson. Jack, Kenny reasoned sadly and later told Jackie, “would have been pleased.”
Foster Furcolo, who in ’52, ’53, and ’54 forward had been battling Jack for primacy in Massachusetts politics, now saw the writing on the wall. He was eager to be governor and wanted to tie his campaign to Jack’s. Steve Smith, no doubt quietly amused given the history of distrust and dislike between Furcolo and Kennedy, agreed, but only if Furcolo would pick up the cost of all the billboards, pamphlets, and advertising. Furcolo, seeing the inevitability of a Kennedy win in November, happily agreed.
Kenny told Steve, “That alone gets my respect for you forever!” The two men chuckled. Despite having only one central headquarters and not paying for the advertising, the Kennedy campaign was nevertheless the most expensive Senate campaign up until that point. With an eye toward 1960, Joe Kennedy was taking no chances.
As Election Day dawned, though Kennedy’s victory was never in doubt, Kenny, Larry, and Dave felt the pressure to deliver a landslide victory. Their opponent, Vincent J. Celeste, was no real threat to Jack, but as Jack noted to Kenny and Dave on Election Day, “If we don’t get a majority of more than five hundred thousand, Celeste will be the real winner.”
To win by such a margin meant that they would need at least two million people to go to the polls, not an easy task in an off-year election.
Yet Dave Powers was confident, noting later to Kenny that “nearly everybody in Massachusetts, Republicans and Democrats alike, had been thrilled by Jack Kennedy’s performance at the 1956 Democratic Convention in Chicago.”
He was sure that meant they would come out and vote. The operation they put together in Jack’s 1958 Senate race was an expanded, more efficient effort than in his first Senate campaign in ’52. This time Kenny and Larry, having learned from experience, made sure to get out the vote as much as possible.
This included, as Kenny put it, a two-channel approach: “the senator making personal appearances in as many towns and cities as possible, as well as large numbers of volunteer workers enlisted for door-to-door canvasing in every community.”
This would include some three hundred thousand signed pledges to vote for Kennedy. It would also involve an extraordinary effort of sending out 1,240,000 copies of a tabloid-style newsletter describing the senator’s past accomplishments and future aims.
On election night, all that personal outreach paid off. Close to two million people—1,952,855 to be exact—actually went to the polls and voted.
It was an off-year-election record. Jack would receive 73.6 percent of the votes, giving him 1,362,926, which provided an incredible 874,608 margin over Celeste. It would turn out to be the biggest majority by which any candidate had won the Senate in Massachusetts and the largest majority won by any senatorial candidate across the nation that year.
Kenny said with satisfaction, “His showing was much better than even he or we had hoped for. His victory attracted much attention all over the country, and he came out of the 1958 election a much more prominent candidate for the presidency.”
At Joe Kennedy’s apartment in Boston on election night, the Brotherhood watched the returns with Jack and Jackie, a mixture of anticipation and excitement in the air. By 2:00 a.m. it was over, and Jackie and Jack returned home.
Joe, Kenny, Larry, and Dave stayed up a bit longer to talk. “It was not that we weren’t excited,” Kenny said later. “We were excited, but we were already thinking about the next ball game.”
They had succeeded in demonstrating that Jack could achieve a big win at home, putting him on the national map as a viable candidate for the presidency. This was done for the voting public across the nation, but also for the party leaders, who watched Jack’s team stack up an impressive set of numbers for an off-year election. The plan for 1960 was coming together.
