by Thomas Maier
When their sons grew older, the Kennedys sent Jack to the Canterbury School in New Milford, Connecticut, a boarding school for upper-class Catholic students, where Rose hoped her son’s inquisitive mind and his restless soul would be inspired. At Canterbury, Jack’s health suffered terribly, with constant fevers for unknown reasons. A frail thirteen-year-old freshman with barely skin on his bones, Jack tired of being treated by the school’s doctor for weeks on end; at dinner, rather than chatting with the rest of the kids, he sat quietly next to the doctor and the headmaster’s wife, hardly any fun. Jack’s eyes gave him constant trouble, his sight weak enough that for a time he wore glasses. In his letters home, though, he kept a generally upbeat and humorous tone, recalling how he tried to sing Catholic hymns—the “Kyrie Santus [sic], Agnus Dei, and so on”—while his voice cracked. The Agnus Dei comes at the most solemn portion of the Mass, the consecration, when the school’s choir would chant in Latin, “Lamb of God,Who takest away the sins of the world, have mercy on us.” The teacher suspected Jack of fooling around irreverently until he got a good listen at this hormone-stricken youth. “My voice must be changing because when I go up, it sounds as if Buddy (the dog) was howling,” he wrote to his parents.“I go up another note and Buddy is choking. Another note and Buddy and me have gasped our last.” His report card at Canterbury for the fall of 1930 was a disappointment. Although he earned “Good” grades in math, science and English, he received only a “Fair” grade of 75 in religion, and a nearly failing grade in Latin.“He can do better than this,”Nelson Hume, Canterbury’s headmaster,wrote on the report to Kennedy’s parents, underlining the Latin grade. “In fact, his average should be well into the 80s.”Aware of his mother’s religious concerns, Jack started another letter to her by underlining that he’d just finished breakfast and “am going to chapel in about two minutes.” Canterbury students such as young Jack Kennedy not only learned the central beliefs of the Roman Catholic Church but also reflected on their meaning and how they might apply to their own lives.“We have religious talks on Tuesday and Catacism [sic] on Wednesday,” he informed his mother. Rose noticed the Catholic school teachers were not helping her son’s poor spelling.“We have chapel every morning and evening,” Jack wrote, “and I will be quite pius [sic] I guess when I get home.”
Jack’s difficulties at Canterbury were endured not only in the classroom and the doctor’s office but on the sports field as well. Unlike some teenagers who already possessed adult bodies, Jack hadn’t grown yet, and his small stature only added to his problems. “Football practice is pretty hard and I am the lightest fellow on the squad,” he wrote home.“The heaviest is 145 pounds—five pounds heavier than Joe. My nose,my leg, and other parts of my anatomy have been kicked around so much that it’s beginning to be funny.” Another Canterbury student, Robert Sargent Shriver Jr., who would become Jack’s brother-in-law, remembered Jack as a “very wiry, energetic, peppy youngster . . . who did extremely well playing on the lightweight football team.” Despite his jaunty tone, though, Jack wasn’t well. Before the year ended, he was forced to drop out of Canterbury because of illness. Though Jack’s difficulties as a teenager at Canterbury are hardly mentioned by his biographers, the disappointment of that year led to one of the most significant decisions in the life of the future president. He would never attend a Catholic school again.
THE FOLLOWING YEAR, after catching up with the help of a private tutor, Jack joined his older brother at Choate, one of the nation’s most exclusive private schools and patterned after Eton, the elite British boarding school. His parents, though, still feared for their son’s almighty soul.
During the summer of 1934, after a short stay by the two boys at the Gabriel Laymen’s Retreat in Brighton, Massachusetts, the priest in charge wrote a letter to Rose, generally praising her “fine manly boys—so sincere” before getting to the point. He confessed to Rose that he feared for their piety. Far more than mere apostates, Father Nilus McAllister warned Rose, her boys might become indifferent to their faith or,worse, doubters. Shaken by the priest’s concerns, Rose sent the letter to her husband, who was away on business, and he sent his own reply back in the mail. In his estimation, the two boys were “very critical and rather of an inquisitive frame of mind,” Joe explained to the priest. He further mentioned that Joe Jr., two years older than Jack and already a Choate graduate, had started that fall at Harvard and would be in contact with the St. Paul Catholic Club on campus where he’d meet “people of a more rational point of view.” But there was no sense in defending his younger son. “As far as Jack is concerned, I am very worried,” Joe admitted to the priest.“I did try him at the Catholic school—Canterbury—and feel I completely wasted a year of his life. We made every effort to interest parish priests near the Choate School, which he attends, but with no help or cooperation whatsoever—a fact, I believe, to be a disgraceful proceeding on the part of the clergy.” Expressing his appreciation to Father Nilus for his warning and enclosing a further check “to defer” the retreat’s expenses, Joe Kennedy promised that he and his wife would be “more insistent on attention paid to this obligation” with their boys in the future.
Joe Sr. began to bear down on Jack, aiming to rid him of his carelessness and instill more order into his life. His son’s dismal year at Canterbury was in stark contrast to Joe Jr.’s success at Choate, where he excelled as a student and an athlete. In cheering his eldest’s overall performance, Joe Kennedy told his namesake:“There is not much that a father can do to make his boy’s career a success—it rests entirely upon the boy.” His parents didn’t have to worry much about Joe Jr. He showed the kind of industriousness, the stick-toitiveness, prized by his father and the unquestioning religious faith valued by his mother. When Joe Jr. later studied at the London School of Economics with the brilliant socialist Harold Laski, he was quizzed about the Catholic Church during a discussion with Laski’s wife, Frida. “I don’t know the answers to all those questions but I know the Catholic Church is right, anyway!” young Joe insisted. (Laski was bemused by young Kennedy’s talk of becoming America’s first Catholic president. During their class trip together to Soviet Russia, Frida recalled young Joe Kennedy’s “RC reaction at the museum of anti-religion. I can see him to this day in all amazement.”) To his parents, Joe Jr. was a true defender of the faith. Rose encouraged religious training for her sons as well as her daughters because it provided “a sense of responsibility and a sense of security,” and a set of moral guidelines so they “knew exactly what they were expected to do.” Seeking to assure his mother that he was being a good boy at Choate, Jack signed off one letter he wrote home in 1932 by asking,“P.S. Can I be the Godfather to the baby?”—little Edward Moore Kennedy born that year. Rose and her husband were still concerned about their second son. Young Jack had changed from a “funny little boy” who loved life, Rose recalled, into a youth who was “generally a nuisance and wasting his time and the time of a lot of the (school) masters.”
THE EXCHANGES BETWEEN Joe Kennedy and his sons reflected his high expectations for them. In writing to his eldest son, the Kennedy patriarch mentioned traveling up to Choate to watch Jack compete in a football game against Deerfield. “Jack plays tackle and played very well, but still has that careless indifference of his,” wrote his father. At Choate, Jack’s actions were monitored by a coterie of teachers, including Russell Ayres, a former classmate of Joe Kennedy’s at Harvard, who promised to keep an eye on the boy. In this large Irish clan, Joe Jr. took naturally to the role often designed for the oldest child—protector of the small ones—and was treated as a surrogate parent. Joe Jr.’s place as the anointed one, the son most like the father, most likely to succeed and realize his father’s ambitions, are implicit in Joe Kennedy Sr.’s letters. They also expressed strong misgivings about his second son:“Mr. Ayres told me that he [Jack] has one of the few great minds he has ever had in history and yet they all recognize the fact that he lacks any sense of responsibility and it will be too bad if with the brains he has he rea
lly doesn’t go as far up the ladder as he should. If you can think of anything that you think will help him, by all means do it.”
Joe Kennedy’s letters to his second son cut him no slack. One well-written letter from Jack was notable in his father’s judgement because, as he later wrote back,“there seems to be a forthrightness and directness that you are usually lacking.”Yet, Joe Kennedy also could be a thoughtful parent, careful not to push his son too hard. His remonstrations were designed to kick-start Jack’s ambition. “Now Jack, I don’t want to give the impression that I am a nagger, for goodness knows I think that is the worse thing any parent can be, and I also feel that you know if I didn’t really feel you had the goods I would be most charitable in my attitude toward your failings,” he wrote in a December 1934 letter. “I am not expecting too much and I will not be disappointed if you don’t turn out to be a real genius, but I think you can be a really worthwhile citizen with good judgment and good understanding.” Although Joe was judicious in his comments about Jack’s best friend at Choate, Kirk LeMoyne “Lem” Billings, a bespectacled pal who became Jack’s lifetime friend, he subtly implied that Billings wasn’t always the best influence for his son. “After long experience in sizing up people, I definitely know you have the goods and you can go a long way,” Jack’s father implored.“Now aren’t you foolish not to get all there is out of what God has given you and what you can do with it yourself.” His language resonated with the biblical adages that Rose taught the boys—especially St. Luke’s instruction:“To whom much is given,much will be expected.” In the spring of that school year, Joe showed little patience with his son’s poor performance. “Don’t let me lose confidence in you again, because it will be pretty nearly an impossible task to restore it—I am sure it will be a loss to you and a distinct loss to me,” Joe reminded him.“The mere trying to do a good job is not enough—real honest-to-goodness effort is what I expect.”Aware of their parents’ expectation, both Joe and Jack Kennedy faced additional hurdles as Catholics at Choate. Pupils were required to attend Protestant chapel services daily, the Catholics standing mute as psalms were recited. (Roman Catholicism was not the only religion tracked. As apparently part of the screening process, Choate asked each applicant’s guardian: “Is the boy any part Hebraic?”) With other Catholic students, Joe and Jack had to attend Mass at a church in downtown Wallingford while the religious needs of their Protestant peers were tended to on campus.
Jack’s biggest crisis at Choate was caused by his wiseacre behavior, which upset George St. John, the school’s headmaster. In his sermons dedicated to upholding the ideals of Choate, St. John routinely derided the “muckers” who caused problems in the school. Kennedy, Billings and their pals conspired to form their own “Muckers Club.” When the Choate headmaster found out about the boys’ mockery, he summoned Joe Kennedy to a meeting at the school about his son’s poor behavior and threatened to expel the impudent young man. During the meeting, Kennedy scolded his son, who was seated by his side, but reminded the headmaster that the term “mucker” was for many years a slur used against the Irish. Years later, the headmaster still couldn’t help noting the family’s ethnicity. “Jack’s father didn’t hold back—in fact, he spoke very, very strongly, and also with Irish wit,” wrote St. John about the meeting. Privately, Joe radiated with anger toward his son, but kept a cool head while convincing the headmaster not to throw Jack out. Shaken by the experience, Jack nevertheless graduated on time and, despite his mediocre grades, was voted “most likely to succeed” by his amused classmates.
Generally, the Kennedy boys fit amiably enough into life at Choate, though their status as Irish Catholics remained an unspoken barrier. At Choate and later at Harvard, another bastion of Brahmin culture, the Kennedy boys sought friendships mainly with Irish Catholics. Jack roomed with Torbert Macdonald, a Boston Irish Catholic from a modest family, and Joe’s best friend was Ted Reardon, another Boston Irish Catholic, who worked his way through college. Bobby’s roommate and closest friend at Harvard, Ken O’Donnell, was an Irish Catholic from Worcester.“A sociologist or a psychiatrist might make something out of a study of the friends that the three older Kennedy boys sought at Harvard,” commented writer Joe McCarthy in his 1960 book about the family.“Selecting such friends at Harvard instead of continuing an association with the upper-crust types in their own wealthy economic level whom they had known in prep school, the Kennedys made an interesting reaching grasp at the racial, social, religious family roots from which they had been removed as children.” McCarthy contended this assimilation process went only so far with this generation of Kennedys: “You can take the boy out of Irish Boston but apparently it is difficult to take the Irish Boston out of the boy.”
At Harvard, Jack couldn’t gain acceptance into any of the elite clubs because of his religion.“Jack Kennedy was part of the Irish contingent, the Catholic contingent, and that set him apart somewhat,” recalled a former fellow student Donald Thurber. “The class was, in those days, just dominated by a WASP atmosphere. And Kennedy didn’t fit into the mold at all. Do I think Jack Kennedy ever suffered ethnic prejudice? Well, yes, I think so—because he was such an obvious Boston-Irish type.” To many at Harvard, the Kennedys were Wall Street hustlers rather than old money, and Mayor Fitzgerald the very epitome of outlandish Irish ethnicity beyond the ivy walls of Cambridge. Joe Jr. endured the same treatment at Harvard. But Jack’s friends prevailed on one group, the Spee Club, to let him in. “It’s wrong that Jack Kennedy can’t get in a club,” said Bill Coleman who, along with Jimmy Rousmaniére, insisted that the club accept them as a threesome or not at all. Jack remained particularly grateful to Bill Coleman, reared in an Episcopalian and Republican family, for helping him overcome this social barrier, a feat neither his father nor brother ever accomplished. Torby Macdonald, despite his popularity and athletic accomplishments, didn’t get into the Spee Club because he was perceived as too Irish, certainly not as polished as his roommate. As the first, Jack learned how to make himself acceptable to the WASPs at Harvard, in his polished speaking manner, his stylish appearance and engaging yet deflective sense of humor—all skills he’d later employ on a grander scale.
It is understandable why teenagers from a minority group, away from home for months at an institution sometimes hostile to their religion, would find comfort with friends who shared the same cultural touchstones. In this world, the Kennedy sons seemed to find comfort in the shared Irish Catholic background of their inner circle of friends—a pattern often repeated within the family. In his own pursuit for wealth and acceptance, Joe Kennedy relied on a rear guard of Irish Catholic cronies, such as Eddie Moore, an Irishman educated in the public schools of Charlestown. (The New York Times once described Moore as “Irish as a clay pipe.”) These men were born several rungs down from the Kennedys on the social ladder, and yet, through some alchemy of similar heritage and experience, they could be trusted with the most intimate secrets of their Kennedy friends. This pattern of friendships would continue into the White House, where Jack’s “Irish Mafia” of confidants, including O’Donnell, existed on a parallel plane to the tweedy official world of State Department experts and Foreign Service diplomats.
JACK KENNEDY’S SENSE of ethnicity and religion, like other aspects of his personal character, was always hard to decipher. Each version of reality, as attested in the numerous volumes written about him, seemed to depend on who was doing the looking. When she wrote her 1974 autobiography, Rose Kennedy asked Jack’s best friend at Choate, Lem Billings, to recall their school days; he claimed the worst thing they ever did, besides the Muckers Club fiasco, was to keep a messy room and sometimes arrive late for class. “Some of our [Muckers Club] members, I expect, did break the school code of conduct by going into town and smoking, drinking and so forth,” he allowed. Two years later, in a biography of JFK written by an old Harvard friend and his wife, Lem Billings revealed another, quite different escapade, which happened while the Choate students were on vacation: “Another ti
me I remember, when Jack first got laid. What a night!” enthused Billings, recalling how Kennedy and another pal, both seventeen, lost their virginity in a Harlem whorehouse (“they were white girls of course”) and then panicked at the thought of contracting venereal disease. Lem accompanied them to a hospital for treatment. “These salves and cremes and a thing shoved up their penis to clean it out,” Billings recalled.“They came home, still sweating. They couldn’t sleep.”
For a young man steeped in the conservative mores of the Catholic Church, the secrecy and shuffling surrounding sex—as well as the fear of punishment—were all part of the thrill for Jack Kennedy. His handwritten letters to Billings, now entombed in the Kennedy Library,were replete with adolescent musings about sex, masturbation and his exploits with women, paid or not. Although the tales are undoubtedly exaggerated, given his bad back and sickly body, young Jack one summer still dreamed of the nurses who came into his hospital room while he was being treated at the Mayo Clinic and serviced him sexually as well as medicinally. In Kennedy’s world, with its images of madonnas and whores, there were good girls for marrying and bearing children—exemplified by his mother, Rose—and other girls for partying and quick sexual encounters. Lem and Jack knew the rules and delighted in breaking them without getting caught. Kennedy seemed convinced that his Saturday night excesses could be forgiven if he said enough prayers at Sunday morning Mass.
Sex outside marriage loomed as a mortal sin, the most serious offense against God. Catholics were taught by the Irish priests that sex served God as an act of procreation—adding to the splendor of divine creation—and never solely for the pleasure of the participants or the enjoyment of the act itself. If eating meat on Friday, missing Mass on Sunday and going to restricted movies were all mortal sins, as the priests commanded in the 1920s and early 1930, then surely Jack Kennedy’s reveries were taking him along the road to hell. If that was his eternal fate, he’d surely meet some of the other men in the family on the way. (Year later, when told his father was seen chasing after some young woman at a racetrack, JFK could only say,“When I’m sixty, I hope I’m just like my father.”)
