A Place in History: Inside Jacqueline Kennedy’s Unique Bond With Son John F. Kennedy Jr.

Jacqueline Kennedy Onassis always encouraged her son to go for it, to follow his heart, take risks and not get swallowed up by the burden of expectations. She was proud of the young attorney, who was also a tireless athlete who would trek into the wilderness by himself, climb mountains, scuba dive and tear through the streets of New York on his bicycle.

But she didn’t want John F. Kennedy Jr. anywhere near the cockpit of a plane.

“Please don’t do it,” the former first lady of the United States told John, one of the two surviving children she had with President John F. Kennedy. “There have been too many deaths in the family.”

Jackie gave birth to a stillborn daughter they named Arabella in 1956, and their infant son Patrick died two days after he was born, three months before Kennedy was assassinated. JFK’s older brother had been killed on a bombing raid while serving in World War II, and a younger sister died in an air crash four years later. Robert F. Kennedy was gunned down in 1968; his widow, Ethel Kennedy, had lost both of her parents and, separately, a brother in plane crashes. Sen. Ted Kennedy was seriously injured in a 1964 crash that killed two others. Jackie’s stepson Alexander Onassis had died at 24 in 1973 when his plane crashed right after takeoff. 

Why tempt the Fates, which always seemed to be swirling around the Kennedy family? Why give that rumor of a curse any more fodder?

So JFK Jr. put the plan aside to ease his mother’s mind.

Jackie died in 1994. Soon after, John met his future wife, Carolyn Bessette, and in 1995 he started a magazine, George, so he didn’t have a lot of free time. But toward the end of 1997, he decided to pursue that lingering goal of his and enrolled in flight school. 

According to biographer Christopher Andersen, Ted Kennedy and Jackie’s longtime partner Maurice Tempelsman had sworn to her when she was dying to do everything they could to stop John from learning to fly. Tempelsman knew that she had nightmares about her son being killed in a plane that he was piloting, and neither he nor Ted would go up in the air with John unless there was a seasoned instructor up there too.

And neither would Carolyn, who, when she found out that John had secretly enrolled in flight school that December, told him she had “a bad feeling” about it.

Everything went wrong on the night 20 years ago that JFK Jr. was killed, along with Carolyn and her sister Lauren Bessette, when his Piper Saratoga crashed into the ocean while en route to Martha’s Vineyard from New Jersey. They were two hours behind when they originally planned to leave, the flight instructor who was going to accompany them canceled, John was out of a cast but still on crutches six weeks after breaking his ankle in a light-parachute crash and, while he was a licensed pilot, he hadn’t yet earned his instrument rating. And the conditions simply prevented him from seeing any of the lights below from up in the air.

Jackie, who would have turned 90 on July 28, was spared what would have been the most crushing blow she’d suffered yet in a life that, while scrutinized and celebrated to no end, was pocked with one tragedy after another.

The dazzling first lady turned style icon, architectural preservationist, book editor and ever-enigmatic public figure always remained the country’s most well-known widow, shrouded in an aura of sadness.

On Nov. 25, 1960, President-Elect John F. Kennedy was in the air, flying back from Palm Beach, Fla., to Washington, D.C., when he got word that his son had been delivered via emergency C-section. He had actually been flying to Palm Beach and was almost there when he found out Jackie had gone into premature labor, so they turned around immediately.

Though the public was none the wiser, John F. Kennedy Jr. spent the first six days of his life in an incubator to allow his lungs to further develop, and overall he and his mother remained in the hospital for two weeks. Jackie, who also underwent surgery, would need an extensive recovery period, just when she was supposed to be getting her young family ready to move into the White House in January.

The first lady needed a Dexedrine pill to make it through the night of Kennedy’s inauguration, and even then only summoned the strength to attend three out of five inaugural balls.

“I always wish I could have participated more in those first shining hours with Jack,” Jackie later said in a series of interviews for an oral history project housed at the John F. Kennedy Presidential Library. “But at least I thought I had given him our John, the son he had longed for so much.”  (There was little to no frank public talk about pregnancy or parenting, let alone postpartum depression, among the celebrity set in those days.)

As would become a resounding theme throughout her whole life, privacy for the 31-year-old new first lady was paramount—she later had no qualms about shutting longtime friends out of her circle if they ever breached her trust, or otherwise shared details from their personal lives with the outside world—and she was determined to keep 3-year-old Caroline and 3-month-old John-John out of the public eye as much as was possible.

She waited until their White House bedrooms were completely furnished and decorated before she brought them up from Palm Beach.

“I want my children to be brought up in more personal surroundings,” she told her White House social secretary Tish Baldrige, per Christopher Andersen’s 2014 book The Good Son: JFK Jr. and the Mother He Loved. “I don’t want them to be raised by nurses and Secret Service agents.”

Jackie recalled wondering how they were going to function at 1600 Pennsylvania Avenue. “I’m afraid it will always be a little impossible for the people who live here,” she mused. “It’s an office building.”

Though they each had a dedicated nanny, Jackie considered herself a hands-on mother, and the president too was determined to be the kind of affectionate parent he didn’t have. In a marriage plagued by his infidelity and health problems and overshadowed by Kennedy’s destined place in the political firmament, their kids were a common goal, their care something to focus on during their roughest patches.

“It isn’t fair to children in the limelight to leave them in the care of others and then expect that they will turn out all right,” the first lady said. “They need their mother’s affection and guidance and long periods of time alone with her. That is what gives them security in an often confusing world.”

Speaking of security, personal protection had been an afterthought for Jackie. She had been a prominent politician’s wife since marrying JFK in 1953, when the congressman from Massachusetts had just been elected to the U.S. Senate, and she just figured their bodyguards had all situations under control.

“Jackie always worried about people violating her family’s privacy,” Baldrige recalled to Andersen. “I never heard her say a peep about somebody wanting to do them harm.”

However, on Dec. 15, 1960, authorities arrested Richard Pavlick on a tip that he had made threatening statements about Kennedy, and it turned out that four days earlier he had planned to ram his car into the president-elect’s one morning and blow both cars up with dynamite. But when he went to the Kennedy compound that morning in Palm Beach, he saw JFK saying tender goodbyes to Jackie and their children and was too touched to go through with it. Still, the man vowed, he would “get” Kennedy.

Pavlick was institutionalized until 1966.

“We’re nothing but sitting ducks in a shooting gallery,” Jackie concluded.

And so would begin Jackie Kennedy’s pressing fear for her family’s safety, eased not at all by the fact that President Kennedy famously carried with him the premonition that he would die young and had resigned himself to that fate. His favorite poem was Alan Seeger’s “I Have a Rendezvous With Death.”

But the 35th president of the United States was a doting father and, at least once the children were born, a somewhat more attentive husband. He and Jackie did sleep in separate bedrooms that were connected by a walk-in closet; but in 1963 they had another child, son Patrick, who died at 2 days old of a more severe case of the lung ailment that plagued John Jr. when he was born.

Jackie spiraled into depression and spent four weeks cruising the Aegean Sea with her sister Lee Radziwill and Lee’s good friend, Greek shipping magnate Aristotle Onassis, who hosted the sisters on his 325-foot yacht, Christina. Onassis’ business had been the subject of criminal investigations in the U.S., so both the president and his attorney general, brother Bobby Kennedy, were familiar with him.

Bittersweetly, when Jackie returned to the U.S., knowing she needed to be by her husband’s side as his reelection campaign kicked into gear, the Kennedys became closer than perhaps ever before in their 10 years of marriage.

“I think the most interesting thing about him is that you realize he was just a man, that he lived a life, like anybody else,” JFK Jr. would later say about his father, who he at least thinks he remembers playing with on the floor of Kennedy’s bedroom in the White House and crawling underneath his desk in the Oval Office. He said that he wasn’t sure what he actually remembered versus what memories he acquired looking at now-classic photographs and watching video footage.

“It’s hard to talk about a legacy or a mystique,” John said in 1993, per the New York Times. “It’s my family. It’s my mother. It’s my sister. It’s my father. We’re a family like any other. We look out for one another. The fact that there have been difficulties and hardships, or obstacles, makes us closer.”

They would have less than three years all together in the White House before one of the most piercing images of the Kennedy era became John Jr. saluting his father’s casket during the funeral procession for the slain president on Nov. 25, 1963, his son’s 3rd birthday.

When news of JFK’s death in Dallas was first broadcast, no one was quite sure how to tell his children. Journalist and family friend Ben Bradlee, among the confidantes gathered at the White House in the wake of the news, recalled distracting Caroline and John, telling them stories and playfully chasing them around the residence. Maud Shaw, their nanny since Caroline was born, ended up telling their 5 1/2-year-old daughter that night, but waited until morning to tell John.

“Did Daddy take his big plane with him?” Shaw recalled the little boy asking when she told him his father had gone to heaven to take care of Patrick.

The night before the funeral, Jackie had dinner at the White House with Lee and her husband, Prince Stanislaw Radziwill, and Bobby and Ethel Kennedy; while friends, including Bradlee and Onassis, and more members of the sprawling Kennedy family started the celebration of Jack’s life early, with the help of a lot of alcohol.

In his book Conversations With Kennedy, Bradlee remembered Jackie as seeming “completely detached” at times, “as if she were someone else watching the ceremony of another person’s grief. Sometimes she was silent, obviously torn. Often she would turn to a friend and reminisce, and everyone would join in with their remembrance of things forever past.”

Maud Shaw had dinner with the children and tended to them as usual. She figured John didn’t fully understand what was going on but she still felt uncomfortable when the kids glimpsed what amounted to a raucous party going on in the other room.

The next day, it was Jackie who told John he could salute his father as the horse-drawn carriage carrying the president passed by, on its way from the Cathedral of St. Matthew the Apostle to Arlington National Ceremony. But it was Caroline whom she compared to a little soldier, the girl, who would turn 6 in two days, having assured her mother that she’d take care of her.

“She’s my helper, she’s mine now,” Jackie said. Thinking of the patriarchal dynasty she had married into, however, she also concluded, “John is going to belong to the men now.”

She still held a small birthday celebration for her son, John Jr. opening his presents with the glee befitting a 3-year-old. She and the children spent Thanksgiving with the rest of the Kennedy clan at the family compound in Hyannis Port and she tried to make them a festive Christmas in Palm Beach.

Jackie may have guessed that John would get swept away into the vast maleness of it all, but the boy still stuck out in a good way amid the boys running amok, thanks to his mother.

“Even at the age of 3, John was a complete gentleman,” The Paris Review founder George Plimpton, a confidante of Jackie’s, recalled to Andersen. “He and Caroline were spirited, but they weren’t spoiled brats. They knew how to behave because their mother drilled it into them.”

After her husband’s death, Jackie knew the political historians would have their say, but she took it upon herself to shape and preserve her family’s image and personal legacy. She is responsible for the Camelot mythos, the memory of Kennedy’s abbreviated term as president as a glamorous golden era in which hopes were high, some great things were achieved and even greater things were in the pipeline, and JFK’s death marked the end of something that would never be replicated.

All of which was in a way true, though the gauzy view of Camelot obviously masks an endlessly more complicated picture. And if she was the queen of the fallen king, that made John and Caroline prince and princess of the realm.

What was clear for Jackie, though, was that she wanted to salvage life for her children, to protect them from the rabid attention paid to her and give them a chance to be legitimately happy. John and Caroline turning out alright would be her “vengeance on the world,” she said.

At first she planned to not shake up the kids’ routine. “I’m going to live in the places I lived with Jack,” she said. “In Georgetown and with the Kennedys at the Cape. They’re my family. I’m going to bring up my children. I want John to grow up to be a good boy.”

So they first moved into a friend’s Georgetown residence and she pretty quickly bought them their own townhouse on N Street, but Jackie quickly realized that the press would never leave them alone if they stayed in Washington. Photographers were always outside and just hordes of people in general were always passing by to gawk or linger in hopes of sneaking a peek at the still-devastated widow.

And Jackie was bereft, despite the composed interview she had given to a Life magazine reporter a week after the assasination. Wracked with despair and guilt over what she did or didn’t manage to do that day in Dallas, she thought her life was over. The public collectively wept for, not just themselves and Jackie, but for Caroline and John—a precursor to what Prince William and Prince Harry would experience in the aftermath of the death of their mother, Princess Diana, in 1997.

“The world is pouring terrible adoration at their feet, and I fear for them,” Jackie told interior decorator Billy Baldwin, who she hired to design their new Georgetown abode.

Bobby Kennedy, by then a father of eight (of an eventual 11), gladly stepped in to be there for his niece and nephew, both of whom spent a lot of time at Bobby and Ethel’s Virginia estate, Hickory Hill, in the aftermath.

Bobby would even take John with him to his office at the Justice Department some mornings, where the attorney general’s breaks from work would include games of hide and seek and leapfrog.

At the same time, Jackie worried that her son was starting to think of some of the men he was spending so much time with in those days as father figures, and even had Secret Service Agent Bob Foster, a longtime member of the children’s protection detail (Caroline and John’s code names were Lyric and Lark), reassigned after John referred to him once as “Daddy.”

The kids gave Foster their dog, Charlie, as a parting gift.

Jackie did not, however, mind Bobby stepping in, believing wholeheartedly that he was “going to make sure John turns out as he should.”

In fact, in one of her lowest moments, when she considered ending her life, she asked RFK and Ethel to adopt John and Caroline, so convinced was she that they would be better off being raised by them.

Too haunted in Washington, Jackie started apartment hunting in New York in the summer of 1964. She eventually found a five-bedroom, five-bathroom, 15th-floor unit with sweeping views of Central Park and the Hudson River at 1040 Fifth Avenue, on the Upper East Side. She paid $200,000, oversaw a $125,000 renovation, and the family of three moved in. (It took some months, so they made their home at the Carlyle Hotel in the meantime.)

The press didn’t exactly ignore them, but it was a world away from Washington.

Caroline started school in the fall of 1964 at Convent of the Sacred Heart and John would enroll at St. David’s the following February.

Meanwhile, Bobby Kennedy was running for one of New York’s Senate seats, and the family, Jackie included, was determined that he be elected, pulling out all the stops at campaign events—including a little face time with John, who fearlessly answered reporters’ questions while perched atop the shoulders of Secret Service agents.

Bobby won in a landslide and Jackie—who didn’t vote in the 1964 election, and refused her invitation to President Lyndon Johnson‘s 1965 inauguration—dug into single motherhood.

One of her and the kids’ favorite pastimes was gazing out at the unbelievable view from the windows of their apartment through a high-powered telescope.

Plimpton told Andersen, “John shared his mother’s love of adventure and her tremendous curiosity. The whole business of peering through a telescope as if you were a captain on the high seas or an astronomer—it was just incredibly exciting.”

While there were numerous items in the immaculately decorated apartment that reminded the children of their father, there was exactly one photograph of JFK, a headshot Jackie kept on her dresser.

“She was trying to move on,” Billy Baldwin explained to Andersen, “and she didn’t want Caroline and especially John to have their whole lives dominated by the ghost of their father.”

But while moving to New York and consuming herself with Caroline and John helped her feel somewhat alive again, she started to get depressed as the first anniversary of her husband’s death approached. She couldn’t go anywhere, let alone look at a newspaper or the cover of a magazine, without being reminded of every painful detail.

On the actual day, Nov. 22, 1964, she took her kids to the park and then, knowing their bodyguards were looking after them, found a secluded bench and cried for several hours.

Pressing on, however, she regularly filled the apartment with fellow parents and their children for playdates, sometimes even inviting people they had just met in the park to come over. 

Through it all, even when she started dating again, Bobby Kennedy remained her rock—and, according to multiple accounts, her lover. Even the kids knew that their mother always seemed happiest around Uncle Bobby. (JFK Jr. later seemed to take his father’s rampant unfaithfulness and his mother’s eventful post-1963 love life in stride.)

Bobby had dinner with Jackie and the kids about once a week, Jackie’s former personal assistant Kathy McKeon remembered in her 2017 book Jackie’s Girl. McKeon too noted the fatherly role Bobby was playing in John and Caroline’s lives. “Madam clearly leaned on him, too,” she wrote. 

During getaways to the Cape, “Bobby and Madam were the Kennedys you were most likely to spot swimming farthest out in the ocean, no matter how cold the water was or how strong the tide,” McKeon recalled. “They were probably the biggest bookworms, too.”

Not going for the salacious, McKeon observed, “There was no denying that Madam and her brother-in-law were close. Loss is a terrible love. No matter how much sympathy you have, it’s a kind of pain that can only be felt, not imagined. And when it happens in a swift, horrific instant, there is no such thing as healing. Tragedy leaves you with an open wound, not a scar. I never told Madam that I understood these things, or how, but I could see plain as day that this awful shared knowledge was what made the president’s widow and younger brother care for each other the way they did.”

During the holiday season in 1964, Jackie took the kids skiing and sledding and packing her calendar with social outings.

Just as she pursued the semblance of a normal life, so she tried to fashion one for her kids, starting with directives to the Secret Service to try to blend in so that John and Caroline didn’t feel conspicuous.

Nor were the agents to act like her kids’ servants, she cautioned, informing them that the children needed to tidy up after themselves, carry their own bags, etc. She even told them to lie low at the beach. “Drowning is my responsibility,” she explained, absolving the agency of responsibility “for any accident sustained by the children in the usual and normal play sessions.”

Yet she was simultaneously terrified for their safety, knowing firsthand what sort of people could be lurking just about anywhere.

An agent accompanied mother and son to John’s first day of school at St. David’s and remained in the hallway outside his classroom, according to Andersen, and it became apparent that the 4-year-old could handle himself when he slugged another kid for calling him “John-John.” (He wasn’t considered an instigator, but he would sometimes take a swing if he was being teased.)

Normality is relative, though. John and Caroline’s first trip abroad came in March 1965, a journey to England with their mom to attend the queen’s dedication of a memorial for their father. 

That was the last trip Maud Shaw made with the family, Jackie having let the nanny go after seven years in part because she feared the children were too attached to a parental figure who wasn’t her. Shaw had a bestseller the following year with her book, White House Nanny, having agreed to let Jackie look at the final manuscript in exchange for not being sued.

Jackie, by now a social butterfly at night, walked both kids to school in the morning and tried to pick up John as often as she could. She regularly took them to Hyannis Port and bought her own horse farm in New Jersey for country weekends. Caroline became an accomplished rider, like her mom, but John—though he was adept enough—was allergic to horses.

Also in 1965, they went to Antigua in the Caribbean and on several skiing trips, including one in Gstaad, Switzerland. While in Europe that time, they swung by Italy for a meeting with the pope at the Vatican.

On May 29, 1966, what would have been JFK’s 49th birthday, Jackie gave John Jr. a World War II-era Piper Cub observation plane—it had no engine or working machinery, but it was still a full-size plane that John could sit in and pretend to fly. 

“Jack always said he was going to give John a real plane when he grew up,” Jackie told their friend Chuck Spalding, per Andersen. “Well, it’s a little early, but not how has it, a real airplane.”

On a trip to Hawaii that summer, 5-year-old John accidentally fell into the pit where the pig was being roasted at a luau, but despite suffering multiple burns that required a trip to the hospital, he handled it all quite stoically.

When John was little, people marveled at how polite and unspoiled he was. “I have to give Jackie a lot of credit for that,” Peter Clifton, the headmaster at St. David’s, told Andersen.

When John was about 6, Jackie started taking extra pains to surround him with people who were close to his dad, friends in addition to JFK’s brothers, so that the child would feel closer to, and be less likely to forget, his father.

And in a further bid to make sure her kids didn’t turn into a couple of average privileged Manhattanites, Jackie had Bobby work on imbuing them with the sense of duty that has been a given for multiple generations of Kennedys. Their uncle made sure to open their eyes to the plight of those less fortunate (which technically was almost everybody), and the lessons stuck with them.

Then Bobby decided to seek the Democratic nomination for president in 1968. Jackie thought the idea too dangerous, because look at what happened to his brother, but she remained one of his magic weapons on the campaign trail.

The 42-year-old senator was actually more concerned about the increasing seriousness of her relationship with Ari Onassis, whose business dealings he found shady, to say the least. He fully disapproved of the idea of her marrying him. Onassis thought it might help get the U.S. government out of his affairs, Ari’s aide Johnny Meyer told Andersen.

Jackie, of course, still planned to help Bobby win at all costs, determined to help get a Kennedy back in the White House, but she didn’t stop seeing Onassis.

On June 4, 1968, Jackie attended two campaign events for Bobby in New York, while he was out in California for the primary that day. She had congratulatory flowers and champagne sent to his room at the Ambassador Hotel, even though he didn’t find out officially until 11 p.m. local time that he had won.

Jackie didn’t go to bed until after 3 a.m. in New York, and was asleep for about a half hour until her brother-in-law Stas Radziwill called and asked her how Bobby was doing.

“He’s terrific,” she said, wondering if Stas knew Bobby had won the primary.

“But, Jackie,” he replied, “he’s been shot. It happened just a few minutes ago.”

This time Jackie was home to break the news to her children that something terrible had happened, and she told John and Caroline that Bobby had been shot by a very bad man before she caught the next flight out to L.A. She went right to the hospital and after they were told he wouldn’t wake up, Jackie’s the one who signed the papers to turn off life support, because Ethel, who was pregnant with their 11th child, couldn’t bring herself to do it.

Robert Kennedy died on June 6, having been fatally shot by Sirhan Sirhan in the kitchen of the Ambassador shortly after midnight on June 5, moments after he had given his victory speech.

President Johnson dispatched Air Force One to fly them all back with RFK’s body. Too young to truly grasp how his father’s death leveled his mother, John Jr. could sense it this time.

“I hate this country,” she told journalist Pierre Salinger, her husband’s White House press secretary, the day after Bobby’s funeral. “I despise America and I don’t want my children to live here anymore. If they’re killing Kennedys, my kids are the number-one targets. I have the two main targets! I want to get out of this country.”

So she married Ari Onassis, who was 29 years her senior, on Oct. 20, 1968, in a small ceremony on Skorpios, the groom’s private Greek island—and, though some relatives attended, it was much to the dismay of her family, almost every Kennedy (JFK’s mother, Rose Kennedy, was the only one who gave her blessing) and her society friends. 

Nevertheless, that marked the beginning of her storied Jackie O. period, largely a reference to her enviable style and the persistent mystique that swirled around her.

Onassis didn’t care how any Kennedys felt about him, other than Caroline and John. He lavished them with toys, spent hours playing games and took them for ice cream. Ari also listened obligingly when John would go on about his father and play recordings of his speeches.

Jackie ultimately didn’t leave the country for good.

In the fall of 1968 she enrolled John at the Collegiate School rather than have him repeat the first grade at St. David’s. He may not have liked paying attention in class, but he was already excelling at sports, which earned all the points he needed among his classmates. And the other boys learned quickly not to tease him.

Ari moved into 1040 Fifth Avenue and, though he’s said to have resumed his years-long affair with opera singer Maria Callas a month later, by many accounts the newlyweds seemed quite happy and affectionate with each other.

By the time John started high school, however, Ari’s health was in decline—ever since his son was killed in that plane crash in 1973—and there were rumors that he planned to file for divorce. Jackie remained in New York, where both kids were in school, while her husband lived mainly in Greece.

Widowed again at 45, she found herself looking for a next chapter for herself in 1975 after Onassis died at the age of 69.

The kids had been her primary focus since leaving the White House and she had turned down numerous job offers of varying interest. Jackie, a big reader and who studied in France during college, had worked as a newspaper columnist before her first marriage and wrote POV dispatches from the campaign trail in 1960. In 1975, book publishing called her name, and she joined Viking Press as a consulting editor; she stayed there for two years before joining Doubleday, where she ended up working for almost two decades.

Meanwhile, Caroline was heading off to Radcliffe, but John was still a boy in need of taming.

“My mother was very strict with me,” he later remembered. “Caroline could do just about anything, but if I stepped out of line, I got a swat.”

“Jackie worried more about John than she did about Caroline, who matured quickly and was very influenced by her father,” Jackie’s stepbrother Yusha Auchincloss told Andersen. “Jackie paid special attention to John.”

But he also paid special attention to her.

Since he was a little boy, John had been concerned with his mother’s peace of mind, sensing her fragility and taking pains to protect her feelings when he could.

“He surprises me in so many ways,” Jackie said when John was 6. “He seems so much more than one would expect of a child of six. Sometimes it almost seems as if he is trying to protect me instead of just the other way around.”

In 1976, John went off to boarding school at Philips Academy in Andover, Mass., and when he turned 16 that November, his days with an ever-present Secret Service detail were over. “Free at last!” he exclaimed when he arrived on campus.

While regular trips to the Kennedy compound in Hyannis Port for holidays and family occasions were a given, in 1977 Jackie made sure John didn’t spend too much time with his slew of cousins, not wanting too much of the ungentlemanly side of the Kennedy men to rub off on her son.

Unlike the “wild and undisciplined” pack of boys that flocked to the homes of Ted and Ethel Kennedy on the Cape, John was “perfectly respectful and polite,” Barbara Gibson, family matriarch Rose Kennedy’s secretary, told Andersen. “Clearly the product of his mother’s love and concern,” she observed.

But while he was an elevated version of the Kennedy bro, he still grew up with an unflagging self-assuredness that put common courtesy—arriving on time, remembering to say goodbye when he abruptly left a gathering—on the back burner. He was also legendarily careless and forgetful, which could overshadow his usually good intentions. 

“Jackie used to complain that he was constantly on the move, and that he didn’t always stop to consider the impact his actions would take on others,” George Plimpton told Andersen. “She also used to say, ‘Jack was like that, too.'”

It was Jackie’s idea to send John to Outward Bound in Maine, where at the end of the program he had to live on an island braving the elements alone for three days. He was a natural.

But the teen, a so-so student at Andover, wasn’t exactly maturing at a rapid clip. After he was caught pouring glue down the mail chute of their building in New York, Jackie again took action. She arranged for her son to spend six weeks summer of 1978 working as a ranch hand in Wyoming, where he won over the skeptics who, just looking at him and knowing who he was, assumed he wouldn’t be much of a worker.

Jackie was thrilled when a seasoned wrangler returned to New York that fall.

Caroline was poised and studious and, the shyer of the two, more outwardly like their mother. She also has lived a remarkably private life, at least relative to the circus her brother experienced for seemingly the entirety of his adult life. She graduated from Radcliffe in 1980 and attended law school at Columbia. She met her future husband, Edwin Schlossberg, while working at the Metropolitan Museum of Art.

But in a family that bred politicians like cattle, how to shape John Jr. with both an eye on history and another on his happiness, how to convince him he was absolved of the expectations that were automatically attached to every Kennedy at birth, particularly the males, but also instill in him the sense of duty that members of the family exhibited so proudly?

The summer at the ranch seemingly proved a turning point for the teenager.

“Jackie had a profound sense of responsibility—not obligation—and she managed to impart that to her son,” writer John Perry Barlow, who owned the ranch and remained friends with JFK Jr. for the rest of the young man’s life, told Andersen. “She was one of the great human beings.” 

But though he was deemed a miracle worker for John’s physical and emotional transformation, Barlow said, “he was already a miracle when he got here.”

When he got back to Andover, John worked with the school’s community outreach program, teaching English as a second language two days a week to immigrant students at a nearby junior high.

Jackie threw a big combined bash for Caroline’s 21st birthday and John’s 18th in 1978 at Le Club in Manhattan and the younger set partied until the wee hours. Headlines were made when John’s close pal Billy Noonan started tangling with the paparazzi who were waiting for them to come out at 4 a.m. and, while trying to untangle his friend, John was knocked to the ground. Noonan later wrote Jackie a letter of apology for causing a spectacle.

John spent 10 weeks in the summer of 1979 in Kenya completing a program with the National Outdoor Leadership School before heading to college. (He got into Harvard, his father’s and many another Kennedy’s alma mater, but he passed, knowing he hadn’t gotten in on his own merits.)

The Ivy League still beckoned, though, and John chose Brown University. In college he got really into theater and Jackie would attend his performances, not so secretly hoping that he didn’t take acting too seriously.

“She thought he was destined for greater things,” Andersen told ABC News this month. “She felt it was beneath him… What she wanted for John was the traditional path into politics, which was through the law,”

After graduation, he worked for the New York City Office of Business Development until 1986, attended law school at New York University and, after finally passing the bar on his third try, got a job in the Manhattan District Attorney’s Office as an assistant prosecutor.

And throughout, he remained exceptionally devoted to his mother.

“The single most important thing in John’s life was his mother,” Jackie’s friend Peter Duchin told Andersen. And that feral instinct to protect her never abated.

Per Barbara Leaming’s Jacqueline Bouvier Kennedy Onassis—The Untold Story, he blew up at girlfriend Christina Haag once when Christina, according to John, intruded upon Jackie during the lady of the house’s designated working hours (any time between lunch and dinner) when they were visiting his mother at her home on Martha’s Vineyard, Red Gate Farm.

Though it certainly wasn’t part of his public image as an impossibly suave scion of one of America’s reigning political dynasties, he hadn’t grown out of the temper he flashed at the schoolkids who teased him.

Jackie and Christina actually had a lovely chat, John’s mother not minding at all that the young woman had shown up on the patio while she was out there.

When Caroline married Ed Schlossberg in Hyannis Port in 1986, John was best man, while Maria Shriver was Caroline’s matron of honor.

“All our lives it’s just been the three of us,” John said in his toast. “Now there’s four.”

JFK said once that he did hope his namesake would pursue politics one day, hoping that JFK Jr. would find public service as fulfilling as his old man did, but overall “I want him to do whatever makes him happy—whatever that is.”

John Jr. certainly thought about going into politics, and he obviously moved with ease in that world. When he introduced his Uncle Teddy at the 1988 Democratic National Convention, it seemed to herald the next in a long line of still-chugging Kennedy eras. Ted Kennedy’s bid to primary Jimmy Carter in 1980 had failed, the senator’s personal baggage proving too heavy to carry all the way, but perhaps another Kennedy would live in the White House yet. 

First up, though, John was named People‘s Sexiest Man Alive after his attention-getting speech, heralded as the whole package by Hollywood taste-makers, if not the decision-makers in Washington. In addition to Haag he reportedly romanced the likes of Sarah Jessica Parker, Brooke Shields and Cindy Crawford, and he dated Daryl Hannah for the better part of five years, though Jackie wasn’t a huge fan of the Splash star.

Or anyone he brought home, really, though that tended to have the reverse affect on how he felt.

“John had measured most of the women in his life by Jackie’s opinion of them,” J. Randy Taraborrelli wrote in his 2019 book The Kennedy Heirs. “If his mother approved, John would decide he wasn’t sure. However, if his mother disapproved, as she did with actress Daryl Hannah, John became even more attached.”

And while he and Caroline were close, she wasn’t much of an ally when it came to his love life, either.

“Caroline never approved of any of the women in his life, possibly with the exception of the actress Christina Haag, whom he dated before Daryl,” Taraborrelli told People recently. “He had come to the conclusion that she’d never be happy with anyone he chose. He would just listen and then do what he wanted to do.”

Ultimately, he said, “both Caroline and Jackie were tough on John’s girlfriends because they wanted someone for him who would make them feel like he was being taken care of.”

Novembers remained difficult for Jackie and tended to put her in a melancholy mood. She had returned to the White House only once, in 1971, to view the official portraits of her and JFK, and though she married again and had numerous boyfriends, she always thought of Jack as having been the guy.

But in what turned out to be final years of her life, she seemed to be making peace with her starring role in a most storied chapter of the country’s history.

According to Barbara Leaming’s Jacqueline Bouvier Kennedy Onassis: The Untold Story, she told John over dinner when she was 61 years that, if his father were to come back into her life somehow, she wasn’t sure she would want to be with him.

For the first time ever she made a public show of support for a presidential candidate, Bill Clinton, and she became friendly with both him and Hillary Clinton, hosting her fellow first lady in New York and sailing with the couple on Martha’s Vineyard.

“You have to be you,” she encouraged Hillary.

In a letter he sent to the Clintons after Jackie died, JFK Jr. told the first couple that their relationship with his mother had “helped her in a profound way.”

Jackie found out she was sick at the end of 1993. She had fallen off her horse while riding at her estate in Virginia and the doctor found a lump near her groin during the examination. They at first thought it was just an inflamed lymph node, but ultimately the 64-year-old was diagnosed with non-Hodgkin’s lymphoma and she started chemotherapy in January 1994.

She laughed at what she called her hubris, her belief that exercising and otherwise trying to lead a healthy lifestyle (minus her smoking habit) would protect her from fate’s whimsy.

Caroline, John and Maurice Tempelsman—the diamond merchant was married and never divorced, but was Jackie’s devoted companion for 15 years—were at her side and the apartment was full of family when she died on May 19, 1994, in her own bed at 1040 Fifth Avenue, where she had lived for 30 years.

“Last night, at around 10:15, my mother passed on,” John told reporters who had gathered outside the next morning, waiting for an update. “She was surrounded by her friends and family and her books, and the people and things that she loved. She did it in her own way and on her own terms, and we all feel lucky for that, and now she’s in god’s hands.”

John read from the Book of Isaiah, Chapter 25, at his mother’s funeral at St. Ignatius Loyola Church, while Caroline read the Edna St. Vincent Millay poem “Cape Cod” and Tempelsman read C.P. Cavafy’s “Ithaka.” Ted Kennedy, the de facto leader of the family since Bobby’s death in 1968, delivered the eulogy.

His sister-in-law’s love for her children was “deep and unqualified,” Ted said. “She reveled in their accomplishments, she hurt with their sorrows, and she felt sheer joy and delight in spending time with them. At the mere mention of their names, Jackie’s eyes would shine and her smile would grow bigger.”

Jackie’s coffin was transported right afterward to Washington, where President Clinton spoke as she was buried next to her first husband at Arlington National Cemetery. John and Caroline both kissed the casket before it was interred, and then John lingered in front of the headstones where his father and infant brother and sister were buried.

“In the end, she cared most about being a good mother to her children, and the lives of Caroline and John leave no doubt that she was that, and more,” Clinton said at the grave site. 

Despite the veil of signature Kennedy stoicism, John was devastated.

About a month later, though, John told a friend he felt his relationship with Hannah had run its course and he had met someone else he thought was really special.

Carolyn Bessette, a PR director for Calvin Klein, resisted his charms at first, not wanting to go gaga just because it was JFK Jr., but they got serious fairly quickly.

“John always measured the women in his life by the opinions of his mom,” Taraborrelli told People. “After she was gone, John had to make up his own mind. He went full throttle with Carolyn, which shows a lot of growth and maturity on his part.”

As more of an olive branch gesture than out of deep sisterly feeling, Caroline was Carolyn’s matron of honor when she married John in 1996.

About a month before she died, Jackie had written letters to her children, wanting to lay out her thoughts while she still had her wits about her. To John, she wrote, per Andersen: “I understand the pressures you’ll forever have to endure as a Kennedy, even though we brought you into this world as an innocent.

“You, especially, have a place in history. No matter what course in life you choose, all I can ask is that you and Caroline continue to make me, the Kennedy family, and yourself proud. Stay loyal to those who love you. Especially Maurice. He’s a decent man with an abundance of common sense. You will do well to seek his advice.”

Maurice was also the one who knew how terrified Jackie was of her son learning how to fly a plane, and he had been charged along with Ted Kennedy with discouraging him. But Jackie hadn’t raised John to do anything other than press on and follow his passions.

In an interview with Barbara Walters a couple months after Jackie died, John said that his mother “always encouraged both Caroline and I to make our own way, to not… subordinate our own lives to the expectations of what we should do with our lives.”

And his greatest fear “would be to be faint of heart and…feel that I missed an opportunity or…could have taken a path less traveled that would, had ended into something completely wonderful and unexpected.”

“Flying meant more to him than anything,” Andersen told ABC News. “It meant freedom…Here you have one of the most pursued, hunted men in the world. And ironically, the only place he felt he could be truly free was in the air.”

John and Carolyn’s funeral took place on July 24, 1999, at the Church of St. Thomas Moore, where Jackie regularly took her son and Caroline as children when they were growing up.

“When they left the White House, Jackie’s soft and gentle voice and unbreakable strength of spirit guided him surely and securely to the future,” Ted Kennedy recalled in eulogizing his nephew, five years after Jackie’s funeral. “He had a legacy, and he learned to treasure it. He was part of a legend, and he learned to live with it. Above all, Jackie gave him a place to be himself, to grow up, to laugh and cry, to dream and strive on his own.”

He said, “John was one of Jackie’s two miracles. He was still becoming the person he would be, and doing it by the beat of his own drummer. He had only just begun. There was in him a great promise of things to come…He and his bride have gone to be with his mother and father, where there will never be an end to love.”