These baby steps toward assuming a bigger public profile were dwarfed in September 1988, when People magazine named John “The Sexiest Man Alive.” Many celebrities actively solicited the title, but John knew nothing about it. Unlike previous selections, which included actors Mel Gibson, Mark Harmon, and Harry Hamlin, John was clearly not a professional actor. For the most part, John got a kick out of the label. His mother worried that it would make it more difficult for people to take him seriously, but John, who was proud of his good looks and muscular body, saw it as a badge of honor.
Years later, he said of the story, “It got me my life.” While obviously an exaggeration, it’s true that the designation did add luster to his appeal. He was both a figure of some historic importance and now like a Hollywood star: a perfect mix of power and celebrity. From then on, it became even more difficult for him to go unnoticed, and random people would stop him on the street. “He would be cordial, graceful, and sometimes, depending on his mood, he thanked them,” recalled Christina Haag. “Most of the time, he would just let them talk.”
In November 1988, one month after the People magazine milestone, John got an early taste of the appeal of being the sexiest man alive. He went to Bloomingdale’s department store to sell boxes of Christmas tree ornaments designed by disabled people from six developing countries. He was acting on behalf of a program called Very Special Arts, started by his aunt Jean Kennedy Smith in 1974. Other members of the Kennedy family were also present, including cousins William Kennedy Smith and Edward Kennedy Jr., along with actress Lauren Bacall. But virtually everyone who attended the event came to see John. As he walked onto the balcony wearing a blue blazer, red tie, and corduroy trousers, a collective roar erupted: “My God, it’s him!” Some of the younger women screamed as if Elvis Presley had appeared. The crowd eventually grew so big that the store had to cut off elevator service to prevent more people from reaching the floor.
“I’m here to sell boxes,” John insisted as flashbulbs went off. But clearly, no one was interested in the boxes or his words. They simply wanted a photo. “Turn this way, John! Smile, John!” The newspaper Newsday took detailed note of John’s appearance: “So here is a young man who must cause the hearts of political kingmakers to throb, their palms to sweat. He has the profile of a matinee idol, and crowds seek him out and bestow on him such precious gifts as attention, respect, and even awe.”
A few years after the People headline, Berman and his wife, Victoria, were spending a weekend in East Hampton, where they had been invited to a large party. John was also staying in the Hamptons, and he asked Michael if he could join them at the event. “It was one of those early-nineties celebrity-heavy Hamptons parties where most people seemed to be a well-known bold-faced name,” Berman recalled. They were used to being the center of attention. But once John walked into the room, all eyes turned to him. “It had to be apparent to everyone there that if there were a hierarchy of celebrity, there was John and then there was everyone else.”
In 1989 the Kennedy family had established the John F. Kennedy Profile in Courage Award to honor political figures who adopt unpopular positions for the common good. The award’s name came from JFK’s 1957 Pulitzer Prize–winning book, the same one that John had recently narrated, which recounted the stories of eight US senators who risked their careers by embracing unconventional causes that they believed would benefit society. “Throughout my life, people have come to me and said, ‘I got into government because of your father,’” John stated. “I feel a great pride in that. So, as my father tried to do in his book and in his life, we want to recognize and encourage not only excellence in public service but also rare courage: people who have sacrificed something, taken a position that is politically unpopular and stuck to it because it’s the morally right thing to do.”
In 1992 John and Caroline decided to promote the award by appearing on Good Morning America as well as sitting down for an interview on ABC’s news program Prime Time Live. The award winner that year was Connecticut governor Lowell Weicker, who had enraged many of his constituents by raising taxes. By this point, John had finished law school, started working for the Manhattan District Attorney’s Office, and failed the bar exam twice before passing on the third try.
The extended TV interview would be John’s first, so Berman reached out again to Michael Sheehan. They set up shop in Berman’s apartment and spent three full days prepping. First, the media consultant guided John through a series of straightforward questions. He taped John’s responses and played them back so that he could analyze them. John, he recalled, was “not enthusiastic” about watching the tapes, but he “was willing to learn.”
Once John reached a certain comfort level with the process, Michael moved into more sensitive topics that were likely to be asked in the televised interview. The most obvious was the clip of John saluting his father’s casket. “What’s your reaction to this?” Sheehan asked. “Look,” John responded, “there are things I remember and there are things I don’t remember. I really don’t remember that.” Next, John deflected a question about the many books that had been published digging into his father’s infidelity: “People had this idea that we spend all of our time at Hyannis running around the house singing the score to Camelot.” John made it clear that he possessed an identity separate from his family and did not feel the need to explain or justify the actions of other people, including his father. Finally, Sheehan warned him, “We have to get some really shady questions, because you will be asked them.” He raised the topic of People naming him “The Sexiest Man Alive.” John’s quick-witted response, referring to his failed bar exam: “It beats the headline in the New York Post, ‘The Hunk Flunks.’” After three days of rehearsal, Sheehan judged John ready. “He got a gentleman’s B,” Sheehan said. The biggest problem was that he appeared stiff, uncomfortable, and not expressive enough. “Don’t be so rigid,” he told his pupil as a final word of advice.
This training came in handy, for as much as John and Caroline wanted to talk about the Profile in Courage Award, the host kept returning to their father and his assassination. “You’ve heard the stories about your father,” asked ABC’s Jay Schadler in an obvious reference to JFK’s sexual peccadilloes. “Do you think that had that been dealt with by the press, do you think it would have tarnished the image we have of him?” John replied, “I think the real question is whether or not, given the tenor of the times, my father would have gone into politics at this point.” The host repeatedly tried to provoke John and Caroline into saying something newsworthy about their father. But both of them remained firm and focused. John told Schadler that he and his sister “view my father’s administration through the colors of others and the perceptions of others and through photographs and through what we’ve read. It’s difficult for us to discern much about him independently of what other people’s impressions are.”
When pressed about what he believed happened on November 22, 1963, John responded, “There are people—historians, filmmakers, etcetera—who are going to take money and time studying that. Whatever they find, whatever they decide, it is not going to change the one fundamental fact in my life, which is that it won’t bring him back.” When asked about the Warren Commission’s lone-gunman theory, he deflected again: “I’ll leave it to people to quarrel about or discern or analyze . . . and just walk away from it.” Though the interview rambled, John received his first initiation into the world of answering questions on television. He performed well, steering the focus to what he wanted to talk about and sidestepping questions he did not wish to answer.
That fall, John had an opportunity to run for office when Congressman Ted Weiss died of heart failure at sixty-four. Weiss, who represented one of the most liberal districts in Manhattan, had just won the Democratic Party’s nomination for reelection a few days earlier. The party had to name a successor to serve out his unexpired term and run for a new term beginning November 3. John got a call from Uncle Teddy.
“I’ll get you that seat,” Teddy promised him. “It’s yours. It’s your way to Washington without having to break a sweat.” But after thinking about it for a day, John said he was not interested. It was not just that he didn’t believe himself ready; he also didn’t want to do what was expected. He felt that although he might decide to enter politics someday, he first needed to accomplish something meaningful before joining “the family business.”
Although they rarely talked about John entering politics, Berman always felt that John would have made a great mayor of New York. New York represented a major part of his DNA. “He took greater advantage of the entire city than anyone I knew. He had favorite haunts in every borough. He created excitement everywhere he went, and the entire city was always wide open to him. No restaurant was ever booked, no bike path off-limits, no concert sold out. . . . If there was a golden ticket, it was his.”
Indeed, Berman witnessed firsthand how dramatically John’s presence could defuse a tense moment. In April 1992 riots tore through many American cities after a predominantly white jury in a Los Angeles suburb acquitted four white police officers accused of savagely beating an African American motorist, Rodney King, after stopping him for a traffic violation and being led on a high-speed chase. The jury arrived at the verdict despite the existence of a videotape showing the officers delivering numerous blows to a seemingly defenseless King.
John and Michael were on their way to the airport in John’s convertible when they got stuck in Harlem traffic and heard the broadcast of disturbances breaking out. Instead of hunkering down in his car or fearing that he might be a target, John put down the convertible top and stretched so that he was almost standing up in the car. At some level, John knew that his presence could serve as a calming influence. “You have to understand,” Berman reflected, “people were petrified. Everyone else had their windows rolled up. But John gets up to stretch in the middle of this chaos and fear.” When other drivers recognized John, they started honking their horns. Even African American pedestrians shouted to him. “Hey, John!” said one. “Can you save us from this?”
Berman was stunned by what transpired in those few minutes on Second Avenue. “I knew that day that I had seen something truly extraordinary,” he reflected in 2019. Berman knew John well by the time of this incident and thought of him mostly “as just a more privileged, sought-after, better-looking version of the rest of us.” But what he witnessed that day changed his perception of John and the power of his appeal. “I saw someone—just because of who he was—who was able to lift spirits, elevate the human condition, and bring a sense of calm to a terribly fractured environment.”
* * *
—
Before graduating from Brown in 1983, John had decided to attend law school and, while still in Providence, signed up for a review course to prepare for the Law School Admission Test, or LSAT. John always struggled with standardized tests, and this one was no different. Although he’d earned Bs at Brown and scored only modestly on the LSAT, John applied to some of the most competitive law schools in the country, including Harvard. Roommate Rob Littell said that the only time he saw John “truly dismayed” was when he opened the thin letter from Harvard announcing that he had been rejected. He retreated into his room and did not come out until the next morning.
Before applying to law school, John spent a day with me at Yale University, where I was now an assistant professor of history. He wanted to take a tour of the Yale School of Organization and Management, which had a dual identity as a public policy and business school that attracted people interested in entering the public sector. I sensed that John was still searching for an alternative to law school. The School of Organization and Management offered a prestigious degree, and its admissions standards were lower than those of a traditional business or law school. At the end of the day, however, he chose not to apply.
As the law school rejections began piling up, John wondered whether he might have a poison pen letter in his file—that is, a purported letter of recommendation that turns out to be critical. I was skeptical. John simply did not come close to meeting the statistical requirements for a top law school. While universities do consider a student’s background in order to create a diverse class—and John certainly had a unique upbringing—those factors do not always compensate for mediocre test results. Most likely, in the view of many admissions officers, John was just another rich kid from Manhattan, but he seemed oblivious that places like Harvard would be a long shot. I did not share this with John, but I was teaching bright, ambitious students at Yale who were at the top of their class and had near-perfect test scores, and some of them were being rejected from the same schools. Finally, after a few more rejections, John received a thick letter from New York University welcoming him to the class of 1989.
When he entered NYU Law School in September 1986, Mrs. Onassis suggested that it was time for John to find his own place, sans roommates. “Our extended fraternity run was over,” Littell recalled. Apparently, they left the apartment in a shambles, and newspapers made sure to cover the story. “Somebody put a fist through the wall,” complained the owner of the complex. The landlord sought legal action, and John settled the case out of court. Littell admitted they had not been model tenants, but their infractions, he claimed, were not “the kind of offense that rated national coverage.”
John moved briefly into a hotel before taking over the top floor of a renovated town house on West Ninety-First Street. His mother called Bloomingdale’s and had the entire apartment tastefully decorated. The place was an odd choice, given that the school was located south of Fourteenth Street in Greenwich Village. On nice days, John would ride his bike roughly eighty blocks to Vanderbilt Hall at the south end of Washington Square Park. On other days, he would take the subway.
The first year of law school is always the most challenging. “First year is grueling,” observed Gary Ginsberg, an old friend from Brown who graduated from Columbia Law School, “because that’s when you’re first exposed to the Socratic method of teaching and forced to come to class prepared lest you’re called on and exposed. It’s a numbing, out-of-body experience being called out on the spot and forced to defend yourself before a professor and your fellow students.” The first year is also when students compete for the all-prestigious law review, positions that are determined by a combination of grades and writing. Only those who make the law review have any chance of securing a clerkship with a judge. John struggled, as did many of his classmates. “You have no idea,” he confessed to Christina. “It’s like another language.” An NYU professor later described John’s performance as “unremarkable,” saying that he showed little “evidence of ambition, drive, and vision.”
Although John struggled in the classroom, he made friends quickly. Faith Stevelman, who met him on his second day, said that he “turned out to be completely different than I expected.” She claimed that the press made him appear like “a narcissistic celebrity brat,” but he was actually authentic and down-to-earth. Another classmate noted that John was “interested in school, but he takes things in stride. He’s not one of those guys with the load of books, running around worrying that he’s going to get a bad grade.”
John found at least one familiar face among the sea of students at NYU. Brown classmate Charlie King was in his third year when John arrived on campus. They played together on the law school’s championship flag football team, Capital Punishment. More important, they created an organization, the City Policy Group, that met monthly to discuss relevant topics. At each meeting, one of the fifteen members would pick a topic, do research, and then present to the rest of the group, followed by discussion. Everyone promised confidentiality, which was largely for John’s benefit so that he could express his opinions and not have to worry about them appearing in the New York Post.
The first meeting took place at John’s mom’s apartment. The issue that John had framed for the day was “the
people’s right to know versus an individual’s right to privacy.” This topic was obviously dear to John’s heart. King distinctly remembered John being “adamant” that there existed “a sphere of privacy for everyone.” He was struck by the contrast between John’s strongly held views on privacy and the gracious, gentle way that John dealt with those who invaded his privacy daily on the streets of New York. “Even though he felt fiercely that people had a right not to be bothered,” King reflected, “you could never know from the way he acted in public.”
Law students fight for a handful of coveted internships that are usually awarded based on grades, class rank, and participation in the law review. Although John met none of these criteria, he received a string of prestigious assignments. During the summer after his first year, John won one of six competitive spots to work in the Civil Rights Division of the Reagan Justice Department. Ironically, he worked for William Bradford Reynolds, who was leading the administration’s rollback of long-standing desegregation policies in housing, education, and hiring.
At the end of his second year, John took a $1,100-a-week summer job as an intern at the Los Angeles law firm of Manatt Phelps & Phillips. Charles Manatt, Teddy Kennedy’s college roommate, had just finished serving as the chairman of the Democratic National Committee. Partly because of these connections, many in the firm resented John. “They give him all the easy work,” one lawyer griped. “Shit, I just worked my ass off on a fifty-page brief that bored me to tears, and he gets to iron out a minor contract dispute” involving a rap group. Another complained, “He is so dumb, they can’t afford to give him anything important.” Such criticisms were unfair, as John was certainly a competent law student and likely not the only intern that summer with powerful political connections.
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