‘He had no business flying that plane’: Carolyn Bessette’s ‘lost’ sister revealed. Her poignant three-word comment on the tragedy that changed her life… why her mother still blames JFK Jr

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The woman who lives in the modest, three-bed cottage is quiet, reserved and entirely unremarkable.

She’s known for her long, wavy grey hair and dark-rimmed glasses, and neighbors describe her as friendly, though she’s remained somewhat private during the 21 years she’s lived here.

People have spotted her getting coffee at a local cafe, shopping for plants at the Saturday market, and, as our newspaper reported last month, even shoveling snow from her driveway.

The house, shared by the 61-year-old and her partner Howard, an art history professor, is located in Ann Arbor, just a short five-minute drive from the University of Michigan. The street is lined with trees and mostly populated by students.

The children don’t know who their neighbor really is, or how important her last name is. Most of them weren’t even alive in 1999, the year Lisa Bessette’s life changed forever. The terrible plane crash on July 16th deeply affected this lesser-known Bessette sister, causing her to withdraw from public life.

That night’s crash tragically took the lives of several people, including pilot John F. Kennedy Jr., the son of the former president, as well as Lisa’s twin sister, Lauren, and her younger sister, Carolyn Bessette-Kennedy, who was married to JFK Jr.

Before that evening, Lisa, Lauren, and Carolyn were always together. Lauren and Carolyn, who had successful and visible careers in New York and were generally more sociable, were frequently pictured together, but Lisa felt just as connected to her sisters.

The three friends talked and saw each other frequently. Even as adults in their thirties, Lisa and Lauren continued to think of Carolyn as their younger sister.

The sudden and shocking loss of her siblings profoundly affected Lisa, as anyone would expect when grieving such a devastating loss, especially at a young age.

When Lauren and Carolyn passed away, she was only 34 years old and deeply heartbroken. She was unable to participate in planning their funerals and hasn’t spoken about them publicly in nearly 27 years. Even when contacted by the Daily Mail, she maintained that stance.

No, she didn’t want to talk about her sisters, she said politely, before adding: ‘I never have.’

This also applies to their parents: Ann Messina Freeman and William Bessette, who divorced in the mid-1980s, and Ann’s second husband, Dr. Richard Freeman.

After the accident, the three family members released a short, heartfelt message about their daughters, and then they all withdrew from public view.

Not that all was calm behind closed doors, however.

People say Ann was deeply angry with her deceased son-in-law, believing his lack of experience and overconfidence as a pilot caused the plane crash. She was so upset that she wouldn’t say his name, instead simply calling the former president’s son ‘him’ within her home.

As one friend commented: ‘Ann is still mad at John – she blames him for her daughters’ deaths.’

The tension between the families and the public’s continued interest in John and Carolyn’s story hasn’t faded. Their relationship – the captivating tale of an ordinary woman who won the heart of America’s most eligible bachelor – has been the subject of numerous books, movies, and documentaries, especially surrounding their tragic deaths.

I’ve been following the story of Carolyn Bessette-Kennedy for years, and honestly, nothing has really captured her life quite like the new Disney+ series, ‘Love Story’. It’s a nine-part drama based on Elizabeth Beller’s fantastic 2024 biography, and it just feels like the definitive telling of her story to me.

Love Story is currently the platform’s most popular series, and it’s brought Carolyn and her family back into the public eye.

Despite reports that Ann died in 2007, friends have confirmed she and Richard—who are now 86 and 94 years old—are both living in a comfortable retirement community in Connecticut, New England.

I’ve been following Carolyn’s story, and it’s so touching that she reconnected with her father, William, just before she passed. He’s now in his mid-80s, as far as I know, and living somewhere in the New York suburbs. It’s a reminder to cherish those relationships while we can.

A fter his daughters’ deaths, he too was said to be ‘very bitter’ and ‘living in awful grief’.

J. Randy Taraborrelli, a Kennedy family biographer, explains that the Bessette family intentionally chose to live a private life and have consistently done so over the years.

He believes people tend to assume a lot about them due to the public nature of what happened. However, they’ve largely kept their personal experiences private.

It’s understandable they’ve been avoiding public attention while dealing with their loss. However, the Daily Mail has discovered there might be additional factors contributing to their desire for privacy.

The Kennedy family faced a difficult financial issue, paying around £11.2 million to settle a wrongful death lawsuit filed by the Bessettes.

After a year and a half of discussions, the case concluded in July 2001, preventing a public trial.

Carolyn and Lauren’s mother was considered the main reason for the lawsuit. She was very protective of her youngest daughter, Ann, and didn’t approve of her relationship with JFK Jr. from the beginning. This disapproval was shown in the TV series Love Story, specifically in the episode depicting their 1996 wedding, where she gave a short, warning speech about the difficulties of marrying into a famous family.

That scene really hit me because it felt so real. Apparently, Beller said John was clearly hurt by what his mother-in-law said – you could just see it on his face.

Lisa wasn’t directly involved in the financial issues, but she did receive money as a result. Interestingly, in October 1999, she publicly showed support for the Kennedys by attending a charity concert in New Jersey with several close family members and associates.

Bobby Shriver, a Kennedy family member, accompanied her, as did her close friend Carole Radziwill, who was married to John’s first cousin and close friend, Anthony Radziwill, who is now deceased. However, this support wasn’t universal throughout the Kennedy family.

Grant Stinchfield, an experienced reporter and long-time friend of the Bessette family, served as their spokesperson after the tragic plane crash in 1999. He says strong feelings and accusations still linger surrounding the events of that day.

The investigation into the crash determined that pilot error was the main cause. John F. Kennedy Jr., who had only been flying for a short time and had owned the Piper Saratoga II for three months, didn’t have enough experience with nighttime or hazy flying conditions.

Grant shared with the Daily Mail that the loss from the fatal crash will always be incredibly painful for the families of Carolyn and Lauren. He believes John should not have been flying the plane given the weather conditions and remains angry that his recklessness cost his two friends their lives, which were full of promise.

It’s unclear if Lisa felt the same anger. Friends of Carolyn told the Daily Mail they’d never met Lisa, describing her as very different from her cheerful and outgoing younger sister.

She isn’t actually in the movie Love Story; her character is only briefly mentioned. Lisa Bessette was born in 1954 to Ann, a school administrator, and William, an architect. She was the older of identical twins, and her sister, Carolyn, was born just over a year later.

Oh my gosh, you wouldn’t BELIEVE how much their dad was always gone for work! And then, when they were just kids – eight and ten years old – their parents split up. It totally shaped who they are, you can see it in everything they do, it really stuck with them.

In the film Love Story, Carolyn wears William’s wedding ring as a necklace. She explains it’s not a symbol of her love for him, but a constant reminder that his true character was different from how he appeared.

Lisa was a quiet, thoughtful child, while her sisters, Lauren and Carolyn, were more driven and outgoing. Carolyn, in particular, was striking, inheriting a blend of cool Nordic looks from her father and warm Mediterranean charm from their Italian mother. A former high school classmate remembers the three sisters always making an impression. They were beautiful, popular, and sat with the ‘cool’ kids on the bus. Though Lisa was lovely, she seemed a little more reserved than her sisters.

Lisa studied art as an undergraduate and then earned a PhD in art history from the University of Michigan. She spent two years in Munich researching her dissertation on psalms, using the city’s historic libraries. While Lisa was in school, her sisters built their careers in New York City: Carolyn worked as a publicist for Calvin Klein, and Lauren became an investment banker at Morgan Stanley Dean Witter.

When Lisa’s relationship with John F. Kennedy Jr. made her a public figure, she naturally became a supportive and protective older sister to Carolyn Bessette-Kennedy.

Carolyn found comfort in accompanying Bill to social events like parties and art shows, according to Beller. At their intimate 1996 wedding on Cumberland Island, Georgia, where Carolyn wore a stunning £30,000 dress by Narciso Rodriguez, Lisa and Lauren remained separate from the other guests. Novelist Robbie Littell described both girls as ‘strong-willed,’ adding that he ‘liked’ Lisa and thought she was ‘cool’.

Lisa has become skilled at observing things from afar, a habit born from years of experience. She was in Munich when she learned her sisters’ plane had crashed, and later, back home in Connecticut, she waited with her mother and stepfather for news. Four days later, the sisters’ bodies were found in the ocean.

On July 22, 1999, the three were cremated and their ashes were scattered at sea. Only Lisa, Ann, William, and Richard Bessette were present on the Navy ship USS Briscoe for the ceremony.

Friends mentioned Ann later wished her daughters hadn’t been buried somewhere inaccessible, like a cemetery. A neighbor explained to the New York Post that she felt she had no dedicated place to go and mourn them.

Lisa graduated from the University of Michigan in 2005. While studying, she worked part-time as a contract editor at the university’s art museum.

She met Howard Lay, an art history professor eleven years older than her, and they’ve lived together in a cozy, well-kept house near campus ever since. They never married and do not have any children.

In addition to completing her doctorate, Lisa joined Howard on several summer educational trips to Paris. During these trips, she guided students on tours of Notre Dame. One participant remembers that Lisa and her partner valued their privacy, and students were asked not to take her picture.

A seldom-seen photo, originally shared by family in 2014, shows Lisa and Howard happily seated with Ann, Richard, and other relatives after a meal. More recently, she was pictured near her home in Ann Arbor.

This was the first time she’d been seen in public in nearly thirty years, since a photo taken with Carolyn in New York back in December 1998.

I really tried to get in touch with Lisa and Howard for this piece, but they haven’t responded. I also couldn’t reach Ann, Richard, or William. Honestly, I completely understand why they’re choosing to stay quiet – it’s a perfectly dignified position, and I respect that.

The glamorous lives and tragic deaths of Carolyn Bessette-Kennedy, John F. Kennedy Jr., and Lauren Siskin will always fascinate people. However, for someone who knew the family, like Grant Stinchfield, this is a deeply personal tragedy, not just a news story.

Honestly, all this renewed interest in the Bessettes with the Disney+ show… it’s just ripped everything open again. It brings back all the awful pain, sadness, and anger from nearly thirty years ago, and it breaks my heart to see it. The Freemans – Lisa and her parents, Dick and Ann – they’ve always been incredibly private, a truly wonderful family. No parent, no sister, should ever have to go through what they did, and it just feels so wrong that everyone is digging it all up again. I just wish people would leave them alone and let them finally have some peace.

As someone who’s followed this story for years, and seen its impact on so many, I truly believe this is the perfect way for it to conclude. It feels like the natural, right ending for such a bittersweet tale.

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2026-03-28 15:06