Why the Kennedys keep going back to their Hyannis Port compound after generations of tragedy

• In 1928, Joseph Kennedy bought a white-shingled cottage in Hyannis Port, Massachusetts, for $25,000.
• The community became the home base for the Kennedy family for decades.
• It's also where several tragedies and scandals took place. Yet the family returns every year.

In 1928, the brash Boston banker Joseph Kennedy arrived in Hyannis Port, Massachusetts. He came in a flashy, chauffeured Rolls-Royce, his pocketbook flush and his enormous brood of barefoot children in tow. 

He bought a white-shingled "cottage" on a dead-end street for $25,000 (a little less than $450,000 in today's dollars), doubled its size, added a movie theater on the bottom floor, and named it the Big House.

Even then, the neighbors intuited that this glamorous family would transform their sleepy neighborhood into a destination, the journalist Kate Storey wrote in her new book, "White House by the Sea: A Century of the Kennedys at Hyannis Port." 

Today, the family still looms large over this Cape Cod community, where Joseph, John, and Robert moved into a trio of clapboard houses that would come to be known as the Kennedy Compound.

The John F. Kennedy Hyannis Museum attracts visitors from all over the world. Boats take visitors to glimpse the compound. According to Storey's book, Robert F. Kennedy Jr., a controversial political figure now running his own presidential campaign, offered people a chance to visit the compound in March 2020 in exchange for a $10 donation to his anti-vax organization — and people paid.

Many Kennedy cousins still summer there, despite all the tragedies associated with the family: assassinations (the president's and his brother Robert's), the untimely deaths (John-John Kennedy and Carolyn Bessette crashing their plane on the way to a wedding there, Saoirse Kennedy Hill's recent accidental overdose), the scandals (the Chappaquiddick incident, various drug-related arrests). 

The family returns despite the constant reminders of unrealized greatness and thwarted promise.

"White House by the Sea" examines why. Storey — an editor at Rolling Stone — interviewed 120 people, including dozens of Kennedys, and asked them about the unbreakable bond between the family and this town.

"The pressure and the history there I felt like would be a lot," she told Insider when asked about what compelled the family to keep going back. "But for many of them, it's just where the family is, a lot of the ones who are parents now. It's how their kids know their cousins, because they go to Hyannis Port."

Hyannis Port became a home

Before the Kennedys rolled into Hyannis Port, they had trouble establishing a summer home in coastal Massachusetts. The Protestant elites in these places looked down on Joseph Kennedy, a Catholic and the son of a barkeep, and his wife, Rose, the daughter of Mayor John "Honey Fitz" Fitzgerald of Boston. 

The family, then with five children (they eventually had nine), liked Cohasset, an upscale resort town by Massachusetts Bay. But in 1922, the golf club there rejected Joseph as a member, likely because of his Catholic faith and humble background. Then, the kin discovered Hyannis Port.

The patriarch had no problem joining the golf club, Storey said. 

The nine Kennedy kids would spend idyllic summers there, playing intense games of touch football, racing sailboats, and attending dances. As Joseph moved from banking to Hollywood (his lover, the actress Gloria Swanson, was once a guest at the Big House, Storey wrote) to an ambassadorship under President Franklin D. Roosevelt, he amassed more houses — including one in Palm Beach, Florida — but he never abandoned Hyannis Port.

"As Joe's fortune grew, he absolutely had the opportunity to move to more exclusive communities," Storey said. "But they stayed, and I think a big reason is because of the relationships with the neighbors and because it was a place where they felt grounded and really felt like home."

A connection to the generations

Soon, Hyannis Port was more than home. 

When John decided to run for Senate as a Democrat, Rose and his sister Eunice hosted teas to introduce the handsome World War II hero to their (largely Republican) neighbors. When the then-senator proposed to the socialite and journalist Jacqueline Bouvier, they took their engagement photos at Hyannis Point. When he ran for president, they set up their Election Day headquarters there. 

By that point, John's brother Robert and his growing family (he and his wife, Ethel, eventually had 11 children) had moved to the house behind Joseph's, and John and Jacqueline had moved next door to them. John continued to spend weekends at the Kennedy Compound, sometimes holding Cabinet meetings in his parents' living room. 

It brought a level of fame, scrutiny, and attention the neighborhood had never experienced before.

"It really transformed this very private community," Storey said, adding that tourists would often clip the roses in their garden. "News vans were parked on people's lawns."

Even before John's assassination in November 1963, the Kennedys had their share of tragedies. Rosemary Kennedy, the third child, underwent a lobotomy in 1941 that left her permanently disabled at 22 — her father sent her away after that. (She returned to the Big House, supervised by the nuns from her living facility, only after her father died in 1969.) Joseph Jr., the oldest son, was killed in action during World War II at 29. (His father stayed in his Hyannis Port bedroom for five days listening to classical music when he heard the news.) Kathleen, the beloved fourth child, died in a plane crash in 1948; she was 28.

All were mourned in the cape, along with Robert, who was shot and killed in 1968 during his run for the Democratic nomination for president — just five years after John.

"People have their different coping mechanisms, and for that family, it's sailing and walking along the beach," Storey said, citing the conversations she had with family members. Many would walk "the exact path along the beach when these awful tragedies have happened. There's a connection to other generations through these things, and it's really meaningful for them."

Not everyone could handle the pressure. As teens, Robert Jr. and Bobby Shriver (the son of Eunice Kennedy) were arrested on charges of marijuana possession, creating a media frenzy. Robert Jr. then spent a night in jail after he was accused of spitting on a cop. Joseph P. Kennedy II (Ted Kennedy's son) was found guilty of negligent driving after paralyzing a girl from the chest down in a vehicular accident. 

Jacqueline continued to spend summers there so her children, John Jr. and Caroline, could see their cousins. "People in that community love Jackie," Storey said.

She enjoyed painting and sunbathing nude on the roof of her house while editing manuscripts. (She was distressed one year to find someone had planted marijuana in her garden.) But in 1979, she walked out of the house she had shared with John for the final time, headed for Martha's Vineyard. She didn't bring anything with her, not even her favorite oil painting that she'd done for John in 1960.

Yet Storey recounted the good memories, too: the lavish weddings (Maria Shriver to Arnold Schwarzenegger, Caroline Kennedy's to Edwin A. Schlossberg), the time the Kennedy sibling Pat stole a bus during a scavenger hunt, Jacqueline in pink pants teaching the family how to do "the twist," and Ted making everyone laugh with his "big derriere," as the Kennedy matriarch described it in her diary. 

And, of course, there was the dock, steps away from the compound.

"Sailing is so important to them," Storey said. "It's almost like a religious experience, the way that a lot of them talk about sailing and being out on the water. It's the place where they physically are getting away from the hubbub and the paparazzi and the news crews and the tourists."

And while some family members have found their own summer retreats far from the cape, Hyannis Port will always be associated with the Kennedys. Storey writes in her book: "It's what's left of Camelot."