Taylor Swift was only eleven in 2000, when K. D. Lang released her popular song “Summer Fling” with the lyrics: “The smell of Sunday in our hair/We ran on the beach with Kennedy flair … my new fun thing … my summer fling.” It was one of Taylor’s favorite songs. Twelve years later, she would have the opportunity to actually live the experience with her own summer fling—and not with the wiry Patrick Schwarzenegger, to whose beguiling charm she’d originally been attracted. As it happened, Patrick, who’s an actor, had to leave for work. After he was gone, Taylor set her sights on his more strapping cousin, the brown-eyed, square-jawed, and shaggy-haired Conor Kennedy. She then spent a week (of July 23) with him at his family’s home at Mount Kisco, which is where she got to know him and his story.
Of course, Conor was still deeply grieving his mother; this was an especially dark time for him. Taylor was saddened when she heard the details of how Mary Kennedy had died. She was close to her own mother and couldn’t imagine how Conor was able to go on after facing such tragedy. She admired his strength, his resolve. Then, while getting to know him, she began to understand just how his many life-threatening allergies had impacted his young life. He didn’t confide in her to elicit sympathy, but Taylor’s heart went out to him just the same. She also recognized his vulnerability. “I’m not as crazy about sunsets as the rest of my relatives,” he told her as they sat on the beach and watched vivid colors splash in the sky. “Sunsets feel sad, like maybe the end of things,” he said. “I like the beginnings of things better.”
Though he was four years her junior, she couldn’t help but recognize his quiet maturity. When she asked about the dark history of tragedy in his family and what he may have learned from it, he said he’d come to a simple conclusion: “Life’s messy.” It sounded like the observation of a kid who’d seen a lot, been through a lot, and had stopped trying to make sense of it. Rather, he’d just decided to accept what he couldn’t control and move forward despite it, much like so many of his Kennedy forebearers who’d seen the worst life had to offer yet persevered despite it. Also, he hated being alone, he said. The idea filled him with terror. “I’ve been surrounded by family from the time I can remember,” he told her, according to one account. “That’s how it is with the Kennedys. You’re always with Kennedys. You grow up constantly surrounded by Kennedys. So when you’re alone and there are no Kennedys, it’s terrifying. I don’t know how to do it.” He wondered if his mother felt the same way, if maybe this was one of the problems that had plagued her.
On the twenty-fifth, the couple had dinner at Marcella’s Pizza in Mount Kisco; on the twenty-seventh, they were seen kissing on the beach; on the twenty-ninth, they went sailing on the Cape after going to church in Hyannis Port. By August, Conor and Taylor were being followed everywhere by paparazzi and, in that great, time-honored tradition of Kennedys, attempting to duck them at every turn. At one point, they were photographed making out on one of the piers and frolicking in the ocean, Taylor in a polka-dotted two-piece. They were a gorgeous, sexy young couple. “Wait. I thought she was with Patrick,” Ethel told her son Bobby. He shrugged. “Kids,” he said. He actually approved of the little romance, though. Bobby had been worried about Conor, as he was all his children. He thought it was probably a good idea for him to have some sort of distraction, and certainly Taylor Swift was a pretty good one.
As some Kennedys sat around wondering about Conor and Taylor, matters of greater magnitude were also being discussed on the premises. Typical of the historical juxtaposition of events when it came to culture at the compound, men and women with serious concerns had converged in the Big House in meetings designed to find ways to change the world, while at the same time, just yards away, people frolicked on the beach, seeming to not have a care in the world.
Since leaving office, Patrick Kennedy had become one of the founders of an organization called One Mind, dedicated to the research and exploration of brain studies and mental illnesses. One Mind’s first conference took place in May 2011 in Boston, where leading scientists, researchers, and business leaders from across the country converged to collaborate and share philosophies about neuroscience and strategies for more comprehensive research. As well as Ted Jr. and Caroline Kennedy, Joan made an appearance, the only time she’d been seen in public since Ted’s funeral.
In May 2012, the second One Mind conference was held in Los Angeles at UCLA. Now, a few months later, Patrick was already planning the third. However, because One Mind dealt primarily with the future of research, he felt the need to establish a new organization that would concern itself with present-day issues, such as insurance coverage for those suffering from mental illnesses. He wanted to call it the Kennedy Forum and, to that end, invited some of the country’s leading scientists, researchers, and human rights activists to the compound in August. Their meetings would be the first to take place in the Big House since it had been taken over by the Ted Kennedy Institute. Even Joan attended, saying that she wanted to contribute in any way she could and making it clear that she wanted to continue to be as open as possible about her own mental health issues if it would mean helping others. On that same day, Patrick recalled, “I couldn’t resist pointing out to the group, during a brief lull in the dialogue, that the girl in the bathing suit walking down the path to the docks was Taylor Swift, who was then dating my nephew and probably already composing the song about their breakup.”
In a week or two, it became pretty clear that Taylor was moving fast; she’d become serious about Conor in what some felt was record time. She became so consumed by him, and maybe by the Kennedy lifestyle, that in mid-August she actually decided to buy property on Cape Cod to be close to him. While her decision seemed surprising to some observers, maybe it just showed how easy it was to get swept away by the Kennedys. Taylor spent $4.9 million on a thirteen-room (seven-bedroom) home overlooking Nantucket Sound, with its own private beach and guesthouse. She owned several other homes across the country and considered her manse in Nashville to be her primary residence. Therefore, these new digs near the compound would be strictly for summer use.
“Conor liked Taylor, don’t get me wrong,” said his friend, “but this business of her buying the house on the Cape made him nervous. After all, it was just one property away from the compound. It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy.”
On August 17, a bit of a wrinkle would present itself in this new Kennedy romance when Conor’s cousin Kyle—daughter of Vicki Gifford Kennedy, Michael Kennedy’s widow—married a fellow named Liam Kerr. According to Vicki, who had gone on to a quiet, unassuming life while raising her children after her husband’s death, Conor sent her a text an hour before the wedding reception at the Fairmont Copley Plaza to say he’d forgotten to RSVP. He wondered if he and Taylor could still attend. Vicki said no, absolutely not. Later she would explain that she feared Taylor’s presence would detract from the attention rightly due her daughter on her special day.
Conor and Taylor showed up anyway. As soon as everyone present realized who Conor’s date was, focus shifted from the bride to the Grammy Award–winning pop star, just as Vicki had feared. Upset, Vicki went up to Taylor, introduced herself, and asked her “as nicely as I could” to leave. In return, Taylor gave her a long stare. “It was like talking to a ghost,” Vicki said. “She seemed to look right past me.” She and Conor then just breezed right by Vicki and went on to enjoy the festivities. “Vicki told me that was complete bullshit,” said the reporter Gayle Fee. “While a lot of women might have been like, ‘Oh wow, Taylor Swift,’ not Vicki. Eventually, one of Conor’s cousins came up to him and warned him, ‘Dude, you’d better check yourself. Aunt Vicki is pissed. I think she’s gonna drag Taylor Swift out of here by her ponytail.’ That’s when the couple left the party.”
That night, Taylor and Conor had a disagreement. Apparently, Conor had misrepresented the situation and told her that they’d been invited to the reception. She said she never would have gone had she known they were crashing the party. How could you do that to me? They apparently got past it, though; the next day they visited the gravesite of Conor’s mom, Mary, at St. Francis Xavier Cemetery in Centerville, Massachusetts. Wearing large celebrity sunglasses, Taylor, with her head bowed, seemed to be praying while holding Conor’s hand.
In the days to come, word of the wedding reception misunderstanding was leaked to the media. Kathie Lee Gifford—Vicki Kennedy’s stepmother and the stepgrandmother of the bride—decided to confirm on television that Taylor had been kicked out of the reception. Taylor was, as she put it, “mortified” by the revelation. She immediately had her spokeswoman deny the whole thing and say that the bride was actually “thrilled” that she was present.
She then called Ethel to make sure there were no hard feelings. She explained that when Vicki asked her to leave, there was so much pandemonium going on around her she had completely misunderstood her. Chaos always happens, she said, whenever she walks into a room full of strangers, and that’s why she appeared to be so blank-eyed. It’s also why she stayed. While Ethel was sorry about it, she couldn’t take it seriously. “There are so many more important things to worry about in the world,” she said, spoken like a woman who’s known real problems. “Don’t worry, kiddo,” she reportedly told Taylor. “There will plenty more days in the sunshine.”
Not many more for Taylor and Conor, though. In September, Conor ended it with Taylor. She was disappointed. Thinking they’d have a future together, she’d actually started doodling “Taylor Swift Kennedy” on a notepad just to see how it looked—and it looked pretty good. Luckily for her, though, she had new music being released and wouldn’t have much time to lament the end of her “fun thing,” her “summer fling.” She had to begin promoting the album, which was called Red and which, incidentally, included her tribute to Conor’s grandparents, “Starlight.”
In a couple of months, Taylor would sell the house she bought near the Kennedy compound. Purchasing it had just been a lark. It seemed like a good idea at the time, anyway. It actually paid off for her, though: She made a million-dollar profit. This sale would not mean, however, an end to her friendship with the Kennedys.
In December, Taylor Swift would be honored at the 2012 Ripple of Hope gala in New York for her philanthropic efforts; since the start of her career, she has donated millions of dollars to charity. The annual star-studded event is organized each year by Kerry Kennedy to pay tribute to those committed to social change. Past honorees have included President Bill Clinton, George Clooney, Hillary Clinton, and Vice President Al Gore. It’s named after Bobby Kennedy’s “Ripple of Hope” speech (also known as his “Day of Affirmation” address), which was given in June 1966 in South Africa when Bobby was a New York senator.3
“Taylor is getting the award because my father believed in the power of youth,” Kerry said of the pop star. “Here’s a young woman—twenty-two years old—who has put herself out in the world, and in an incredibly powerful and strong way.”
Today, when Conor looks back on the first summer after his mother’s death, he’s grateful to Taylor Swift. She helped him through a tough time by bringing to it a little bit of romance and just a touch of Kennedy melodrama, which, he had to admit, was actually fun. For her part, Taylor looks back on it as that special time in her life when she got to experience, at least in some small way, getting to know members of the fabled Kennedy family she’d so idolized. “It was one of the best times of my life,” she has said.