HEARTBREAKING STORY: The Final Day Of JFK Jr. And Carolyn Bessette Still Brings TEARS Today CQ💔

John F. Kennedy Jr. was flying Carolyn and Lauren Bessette to Martha’s Vineyard when he crashed on the evening of July 16, 1999

John F. Kennedy, Jr. and his wife Carolyn Bessette Kennedy at the annual John F. Kennedy Library Foundation dinner on May 23, 1999 in Boston, Massachusetts ; Ted Kennedy with sons Teddy, Jr. and Patrick with the flag at half mast.Credit : 

Justin Ide/Getty ; MediaNews Group/Boston Herald via Getty

John F. Kennedy Jr. was flying his plane with his wife, Carolyn Bessette, and her sister Lauren Bessette as passengers, when it crashed into the Atlantic Ocean.

The day leading up to the crash, Friday, July 16, 1999, was more chaotic for JFK Jr. than a typical summer Friday. The editor-in-chief spent much of the day meeting with several media execs in an attempt to turn around his political lifestyle magazine, George.

JFK Jr. had to leave his New York City office no later than 6 p.m., because he had agreed to take his sister-in-law Lauren to the Essex County Airport in New Jersey. Meanwhile, Carolyn had plans to meet them there.

The three of them had planned for JFK Jr. to fly them in his new private plane to Martha’s Vineyard. They would drop Lauren off on the island, and her friends would pick her up, before JFK Jr. and Carolyn would take off again to head to his cousin Rory Kennedy‘s wedding the next day at the Kennedy family compound in Hyannis Port.

Tragically, the three of them never made it to Martha’s Vineyard. At the time, JFK Jr. was trained to fly using visual flight rules (VFR) and in the process of getting his instrument rating (IFR.) The plane he was flying ultimately crashed about seven miles off the coast of Martha’s Vineyard.

About two hours later, their family members and friends began to worry when they discovered that JFK Jr. and Carolyn’s plane still hadn’t landed. A search commenced in the early hours of the morning, later determined that they had perished in the crash.

Here’s everything to know about the events leading up to John F. Kennedy Jr., Carolyn Bessette and Lauren Bessette’s tragic deaths on July 16, 1999.

JFK Jr. and Carolyn were going through a “painful period” in the weeks leading up to their deaths

In the months leading up to JFK Jr. and Carolyn’s deaths, the couple were going through a “painful period” in their marriage, according to friends who spoke about their relationship in PEOPLE editor-at-large Liz McNeil and JFK Jr.’s former assistant RoseMarie Terenzio’s book, JFK Jr: An Intimate Oral Biography.

After the couple tied the knot in September 1996, the paparazzi and press surrounding them dramatically increased. Even after she began adjusting to the heightened media attention, Carolyn was feeling “overshadowed” by her husband, according to JFK Jr.’s friend Steven M. Gillon.

A few days before their tragic deaths, JFK Jr. spent at least one night at the Stanhope Hotel, but accounts vary on how many nights he was there.

Despite their ups and downs, both of them were “really wanting to work through something,” JFK Jr.’s longtime friend Sasha Chermayeff said in the oral biography.

Carolyn initially didn’t want to attend Rory’s wedding but changed her mind

Amid his marital problems with Carolyn, JFK Jr. had agreed to go to his cousin Rory’s wedding, which was scheduled to take place on Saturday, July 17, 1999, at the Kennedy compound in Hyannis Port.

Although the couple previously committed to attend the nuptials, Carolyn was apparently upset over issues in their marriage and told him that she wouldn’t be attending, according to William D. Cohan’s 2019 book, Four Friends: Promising Lives Cut Short.

In her book, Terenzio recalled Carolyn calling her “crying and very upset and not feeling like she wanted to put on a brave face.” At the same time, JFK Jr. knew he’d be questioned about why she wasn’t with him.

Carolyn ultimately changed her mind. Lauren had lunch with her and helped convince her to go to the wedding. Lauren also agreed to fly with Carolyn and JFK Jr., because she already had plans to spend the weekend on Martha’s Vineyard.

Therefore, the plan was set: JFK Jr. would fly the three of them to Martha’s Vineyard, where they’d drop Lauren off and then the couple would make the short flight to Hyannis Port.

JFK Jr. held a staff meeting at George and met with a financier friend, while Carolyn shopped for a dress

At the same time that JFK Jr. was facing problems in his personal life, his professional life was also at a crossroads. George, the political lifestyle magazine he co-founded in 1995, was struggling financially and JFK Jr. was facing even “more pressure to meet advertisers,” Terenzio shared in the Oral Biography.

JFK Jr.’s schedule that day began around 10 a.m. when he met with his friend Peter Kiernan, who was a media financier at Goldman Sachs. During their meeting, they spoke about new funding and business plans, while also talking about “his life and his frustrations and his aspirations and his family, in ways that we never had before,” Kiernan shared in the book.

Later that afternoon, JFK Jr. held a staff editorial meeting, during which assistant editor Matt Owen remembered him having an “unusual tone” and admitted to being “distracted,” per Cohan.

Elsewhere in the day, he met with the CEO of Hachette Publishing, Jack Kliger, to “discuss ways to revitalize George.”

JFK Jr. was in his George office until 4 p.m., when he told Terenzio that he was heading to the gym for an hour, to which she reminded him that he had to be back no later than 6 p.m. Before JFK Jr. left his office for the final time, he emailed his friend John Perry Barlow to send his condolences upon the death of his mother.

Meanwhile, Carolyn’s schedule wasn’t publicly known, but Cohan wrote that she went to Saks Fifth Avenue to purchase an Alber Elbaz dress and later got a pedicure.

Lauren met JFK Jr. at his George office around 6 p.m. to head to Essex County Airport

According to the oral biography, Carolyn called Terenzio earlier in the day and told her that Lauren would meet JFK Jr. in the lobby of his office around 6 p.m. Terenzio left a sticky note in his office as a reminder.

Carolyn also asked Terenzio to get her a car, so she could meet them at the Essex County Airport in New Jersey.

Everyone was running late to the airport

There are mixed reports as to when everyone was originally supposed to leave for the airport. Cohan reported that earlier in the day, JFK Jr. initially called an employee from the Essex County Airport and told them that he planned to arrive to the airport between 5:30 and 6 p.m.

However, he and Lauren didn’t leave until around 6 p.m. JFK Jr. and Lauren, who drove together, and Carolyn all experienced heavy traffic while trying to get to the New Jersey airport from Manhattan.

Lauren and JFK Jr. arrived to the airport a little after 8:10 p.m., per Cohan. Carolyn pulled up to the airport around 20 minutes later, at 8:30 p.m.

JFK Jr. declined help from a flight instructor

Earlier in the day, JFK Jr. informed several people that he was planning to fly his new private Saratoga plane with a flight instructor by his side that night, according to Cohan’s book.

“Don’t worry. I’m flying with an instructor,” JFK Jr. told George executive editor Richard Blow, per Cohan.

However, according to Cohan, because they were running late to the airport and the weather appeared to be clear, JFK Jr. told the flight instructor to head home.

“That night there was a flight instructor,” JFK Jr.’s friend Ed Hill told Cohan. “He said to John, ‘You’re taking off late. There’s cloud cover over the Vineyard. Like most Americans I’m willing to inconvenience myself out of my love for you. I will fly up there with you and bring the plane back, or get my ass back to New Jersey somehow. Don’t go without me.’ “

However, according to Cohan’s book, JFK Jr. assured the instructor that he could handle it and told him, “Go home to your wife and kids.” Bob Merena, the flight instructor in question, later told the NTSB that JFK Jr. told him “he wanted to do it alone.”

They took off later than expected, at 8:38 p.m.

JFK Jr.’s friend Dan Samson was originally supposed to pick he and Carolyn up from the Hyannis Airport around 8 p.m., but JFK Jr. called Samson to tell him that they were late and would now be arriving closer to 10 p.m.

At 8:38 p.m., the Essex County Airport reported that they were cleared for takeoff, and the three departed in JFK Jr.’s plane.

They flew for about an hour until they were around 30 miles west of Martha’s Vineyard Airport, and he started the process of descending. From 9:38 p.m. to 9:41 p.m., JFK Jr. altered the plane’s direction, speed and altitude in an attempt as he began to approach the descent.

According to the NTSB report, JFK Jr., who flew by VFR (visual flight rules) became disoriented and, according to experts, his brain may have contradicting what his cockpit instruments were telling him.

Authorities later estimated that JFK Jr.’s plane crashed into the Atlantic Ocean, about seven miles west of Martha’s Vineyard, around 9:41 p.m. The NTSB’s full final report on the crash can be downloaded here.

Their family and friends began to worry around 11:30 p.m. when they still hadn’t arrived

An intern at Martha’s Vineyard Airport recalled waiting for JFK Jr.’s flight to come in, but he couldn’t access the flight plan, because it was a private plane; he left the airport around 10:30 p.m.

Samson, who had sent an employee to pick up Carolyn and JFK Jr., was the first person to get worried about their whereabouts when the employee returned alone around 11:30 p.m. Samson started making phone calls. When people discovered that their flight took off over three hours ago that they grew seriously concerned.

Terenzio began calling various members of the Kennedy family and Lauren and Carolyn’s family, but nobody had heard from them or seen them.

The Coast Guard began looking for the lost plane around 2 a.m.

The Kennedy family made the executive decision to call the Coast Guard stationed on Cape Cod around 2:15 a.m. on July 17. The Coast Guard subsequently embarked on a search and rescue operation before 4 a.m.

Shortly after, they began locating wreckage from the Saratoga that signaled the plane had crashed. On July 21, divers found all three bodies on the bottom of the Atlantic Ocean.