Carolyn and Lauren Bessette died in 1999 after a plane piloted by John F. Kennedy Jr. crashed into the Atlantic Ocean.

Did Carolyn Bessette’s family sue JFK Jr.’s estate after the deadly plane crash?

Carolyn and Lauren Bessette died in 1999 after a plane piloted by John F. Kennedy Jr. crashed into the Atlantic Ocean.

By Allison DeGrushe

Allison DeGrushe

Allison DeGrushe is a timely SEO writer at **. She has been working at * *since 2025. Her work has previously appeared on Distractify.

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March 27, 2026 10:00 a.m. ET

Carolyn Bessette and John F. Kennedy Jr at the Municipal Art Society Gala. Credit:

Richard Corkery/Getty

- John F. Kennedy Jr., Carolyn Bessette, and Lauren Bessette died in a July 1999 plane crash.

- Carolyn and Lauren's mother, Ann Messina Freeman, sought the right to pursue personal injury or wrongful death lawsuits.

- She later filed claims for "wrongful death and conscious pain and suffering" against JFK Jr.'s estate.

July 16, 1999, started like any other summer day, but ended in tragedy when John F. Kennedy Jr., his wife Carolyn Bessette, and her sister Lauren died in a plane crash off the coast of Martha's Vineyard, Mass. It took several days to locate the wreckage and recover their bodies, leaving family and friends devastated.

Decades later, FX's limited series *Love Story: John F. Kennedy Jr. & Carolyn Bessette* is looking back at their whirlwind romance, the pressures of life in the public eye, and the tragic crash that shocked the world.

The sudden loss hit both families hard, and Bessette's mother, Ann Messina Freeman, reportedly considered suing JFK Jr.'s estate. Here's what we know, including whether she ever went through with it.

How did Ann Freeman cope following the plane crash?

Constance Zimmer as Ann Messina Freeman on 'Love Story'.

Fear quickly took hold in the hours after the plane went missing. According to RoseMarie Terenzio and Liz McNeil's 2024 book *JFK Jr.: An Intimate Oral Biography, *Carolyn and Lauren's mom, Ann, was "panic-stricken."

Terenzio, JFK Jr.'s former assistant, recalled telling Ann not to jump to the worst-case scenario, but Ann responded, "I told him never to take two of my girls up at the same time."

"She was angry. Crying. It was panic, shock," Terenzio added. "It was a hysterical time—everyone was scrambling to figure out how the f--k did this happen. Disbelief."

How did JFK Jr. die? Revisiting the 'Love Story' subject's tragic plane crash

'Love Story' star Constance Zimmer says finale will be 'very, very difficult' to watch

In the months that followed, Ann largely stayed out of the limelight to "mourn privately," per the *Cape Cod Times*. A year later, those close to Ann claimed she was, in the words of the outlet, "still having difficulty keeping control of a life that spiraled wildly into the public domain."

"People talk about Kennedy, Kennedy, Kennedy. But they forget that she lost two daughters," said Mary Marks, a church secretary who helped Ann plan the memorial service for Carolyn and Lauren.

Friends also said that Ann largely withdrew from her social life as she grieved. Marks also recalled the last time she spoke with Ann. After overhearing someone discussing their twins, Ann turned to Marks and said, "I used to have twins."

Did Carolyn Bessette’s family sue JFK Jr.’s estate?

John F. Kennedy Jr. and Carolyn Bessette on May 23, 1999, in Boston.

Justin Ide/Newsmakers via Getty

Ann pursued claims against JFK Jr.'s estate, including "wrongful death and conscious pain and suffering."

A month after the fatal crash, Ann also took steps to protect her legal options. As the *New York Times *reported in August 1999, she filed court papers to handle her daughters' estates and also requested "the right to file personal-injury and wrongful-death lawsuits in the future against 'unknown' people or parties."

Legal experts at the time said that step was routine in sudden or accidental deaths. Depending on the findings, possible defendants also could have included "the company that manufactured the plane, the Federal Aviation Administration, and the estate of Mr. Kennedy."

Manhattan lawyer Harold Lee Schwab noted that a negligence claim could have been brought on behalf of Lauren against JFK Jr.'s insurance carrier or estate.

"Her sister could have a cause of action for negligent operation of the aircraft," Schwab explained. "Given the current state of facts, it certainly would seem that a case can be made out for negligence in the operation of the aircraft."

Did Ann Freeman settle her claim with JFK Jr.’s estate?

Constance Zimmer as Ann Messina Freeman on 'Love Story'.

Yes, Ann did reach a settlement with JFK Jr.'s estate. According to CNN, Manhattan surrogate judge Renee Roth approved Ann's request to "compromise and settle the cause of action" tied to her daughters' deaths in 2001.

As part of the agreement, the estate was cleared of any further lawsuits and claims once the settlement was finalized.

The exact terms were never made public. At one point, a *New York Post *report suggested the payout could have been around $15 million, but Ann's attorney, Constantine Ralli, told CNN that was false. "I don't know where they got that number," Ralli said.

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