Island remembers J.F.K. Jr. plane crash

20 years ago, an ‘eerie,’ ‘somber,’ and ‘sad’ weekend put the Vineyard at the center of the world.


It was 20 years ago today that John F. Kennedy Jr., his wife, Carolyn Bessette Kennedy, and her sister Lauren Bessette took off on a humid, windy, and hazy night in a single-engine Piper 32 Saratoga aircraft from Caldwell, N.J., en route to the Martha’s Vineyard Airport, but never arrived at their destination. 

The trio was headed to a family wedding at the Kennedy compound in Hyannis Port the next day, and left New Jersey aboard the plane Kennedy purchased earlier that year after becoming a licensed pilot.

Large sections of Kennedy’s plane were found in about 100 feet of water 7.5 miles southwest of Aquinnah the following Wednesday, July 21, 1999. The first sign of wreckage was recovered 100 yards off Philbin Beach in Aquinnah.

J.F.K. Jr. was the first son of former President John F. Kennedy and former first lady Jacqueline Kennedy, born during his father’s tenure in the White House. For his entire life, Kennedy was stalked by the paparazzi. He went on to found the political magazine George, and worked as a New York City assistant district attorney. His salute to his father’s passing caisson as a 3-year-old boy is emblazoned in the memories of a generation of Americans. His speech introducing his uncle Ted Kennedy at the 1988 Democratic convention was highly praised, and his own political ambitions were often fodder for political pundits. Were he still alive, he might be in the conversation as a candidate for the Democratic nomination in 2020.

“Up until his death, he was making a mark in different ways,” Peter Ubertaccio, an associate professor of political science and the founding dean of Thomas and Donna May College of Arts and Sciences at Stonehill College, told The Times. “I think J.F.K. Jr. could have had a very successful career in public life — if he wanted to do that.”

That weekend in 1999 saw The Times swamped with media inquiries from outlets both national and international, in a time before Twitter, Facebook, and Islanders Talk. 

In his “At Large” column the week of the crash, former Times owner and editor Doug Cabral said the first call to come into the office after the crash was early Saturday morning. It was from a reporter at a morning daily in Sydney, Australia. He found Cabral’s contact through The Times website.

“We wanted to tell the stories of Islanders,” Cabral wrote, “year-rounders, seasonal residents, and vacationers — involved in the search. We also wanted to describe the effects of the media and government invasion.”

Cabral credits The Times website with giving a voice to people who were strangers to the Vineyard and strangers to the Kennedy family. 

“The story that surprised us, that turned out to be a big story, and our story, though not an Island story, grew all on its own from The Times Internet website,” Cabral wrote.

The Times contacted several people who were on the Island that fateful weekend two decades ago. For many on the Island, it was a weekend marked by not only a flood of media attention, but also the anxiety of having emergency personnel scour the Island beaches for any sign of the crash. The constant beating of helicopter propellers could be heard across the air.

Charlie Cheevers, a lifelong visitor to the Island and an FAA-licensed pilot since 1985, headed out of Vineyard Haven on a freight boat the night of the crash, and remembers the “dense haze” that formed over the Island. He was saddened when he heard the news the next day.

“Given the relatively cold ocean temperatures and the heat mass [the Island] and high humidity — flight conditions over the Island were certainly setting up IMC [instrument meteorological conditions] rules — something that should cause a non-instrument-rated pilot or even a newly minted IFR [instrument flight rules] pilot to consider seeking an alternative airport,” Cheevers said.

Gayle Stiller was working as the house manager of the Vineyard Playhouse the night of the crash. At the end of the performance, Stiller was taking out the garbage and remembers looking up at the moon, which she described as “very hazy, unusually so.” That weekend, her family had a beach day off Moshup’s Trail. She remembers a swarm of police officers driving up and down the beach on ATVs, and helicopters flying through the air looking for any sign of the plane. A state trooper warned Stiller and her family that wreckage and even body parts could wash up on the shore.

“I do remember being very tearful when the plane was found with the bodies still buckled into their seats. And I remember reading the descriptions of the night the plane went down, and how the fog caused J.F.K. Jr. to become disoriented. And I remember feeling so sad for Caroline, losing her only sibling, her brother. But I also remember being glad that his mother wasn’t still alive to suffer this loss,” Stiller said.

The day after the crash, Ted Murphy was on Hancock Beach in Chilmark with his family and friends: “We were worried that something might wash up on the beach that we would have to explain to our young children. It was hard to fathom that the Kennedy family was experiencing yet another tragedy. Very sad.” 

Leslie Lichtman was in the co-pilot seat on a Cape Air flight from the New Bedford Regional Airport to the Vineyard, only an hour before Kennedy set off from Caldwell. Conditions in the air that night were bumpy, and visibility was low. The next day Lichtman was in shock at the news: 

“The Island was quiet, most people home glued to TV sets. We went to dinner with family, can’t recall where, but every restaurant was empty. There was an eeriness and unsettled feeling all weekend.”

That weekend was one Susan Shannon says she’ll never forget, because July 16 is her birthday. When news of the crash emerged, Shannon said, sad crowds of people gathered for updates. Many couldn’t bear the thought of going to the up-Island beaches for fear of finding anything that washed ashore.

J.P. Hitesman was eating at Nancy’s in Oak Bluffs the night of the crash. He vividly remembers the hazy sunset over the harbor. After learning about the crash the next day, Hitesman and his father went up-Island to Aquinnah, where reporters from several national outlets had gathered. 

“I particularly recall talking with the now well-known Shepard Smith … The glare of the news spotlight on the Island was sharp, but quickly receded after the burial at sea in Woods Hole and the subsequent funeral in Manhattan,” Hitesman said.

Famed Vineyard novelist Cynthia Riggs housed a TV reporter from one of the major national networks at her bed and breakfast, the Cleaveland House. 

“Rooms were as scarce for news people as the proverbial hens’ teeth,” Riggs recalled. “She managed to transmit her breaking news to her channel, but needed to check it out on TV before it ran nationally. Well, we do not have television. One of the attractions of our B and B.”

Adam Wilson, the former owner of Adam Cab, was at the airport when an airport official came from the terminal and told him, “John-John’s plane is overdue.” Once it was determined that his plane had gone down, Wilson said, the world’s press descended on the Island. The media scrambled to cover the story. Being the middle of summer, houses were booked, so reporters were put up in network executives’ summer homes. 

For seven to 10 days, eight to ten hours at a time, Wilson rented out his vans to the Boston Globe, the Washington Post, the Christian Science Monitor, and overseas networks BBC and Asahi Shimbun, as the search went from rescue to recovery.

“It was a real tragedy,” Wilson said. “Owning a transportation company that had enough inventory to help cover the event for the media and still operate our other accounts made us an involved part of those days, 20 years ago.”


  1. July 24, 2019

    I’ve flown in and out of MVY many thousands of times since 1980. On July 16, 1999 I flew from MVY to Teterboro NJ and back, then MVY to Westchester County Airport and back about two hours prior to the time of Mr. Kennedy’s crash. On each flight leg I flew under visual flight rules. In-flight visibility in the haze was approximately 3 to 5 miles, with little, if any, visible horizon.

    It’s typical for haze to be limited from the earth’s surface up to a higher altitude. That day “top of the haze” was approximately 5000 to 6000 feet. Above that, in-flight visibility was unlimited with the horizon clearly defined.

    Mr. Kennedy’s presumed flight path was nearly identical to what I had flown four times earlier that day. It was reported that Mr. Kennedy’s enroute flight was at an altitude above the haze, until he needed to descend for MVY. Had he flown over the coastline he surely would have seen lights from the ground and been provided a visual reference. Instead his descent over the open water between Block Island and MVY precluded any outside reference save perhaps lights from a few fishing vessels.

    As an experiment, two days later at dusk and in similar weather conditions, I flew the same eastbound flight path using visual references only. It was achievable, but only due to my level of skill, experience, and a few lights on the ground.

    We can’t know every circumstance of this tragic event, however had Mr. Kennedy promptly recognized his predicament and engaged his autopilot (assuming it was functional) the outcome may have been more favorable. Unfortunately, at that time, standard general aviation flight training did not include much more than cursory instruction on the technicalities of autopilots or, more importantly, when to utilize that equipment.

    Perhaps as a result of Mr. Kennedy’s accident, many of today’s general aviation autopilots include some form of “panic button”, which, with a single press engages the autopilot to promptly bring an aircraft to straight and level flight. The Avidyne DFC90 with a “Straight & Level” button is an example. Last year Garmin on their blog noted:

    Aircraft loss-of-control scenarios in-flight are one of the foremost safety concerns in aviation today. It’s become such a safety concern that it’s landed a spot on the National Transportation Safety Board’s Most Wanted List. At Garmin, we’re doing our part to help put an end to these dangerous events. And one of our tools is our “blue button.”

    Officially referred to as the return-to-level (LVL) mode button, this dedicated button has been incorporated in select Garmin integrated flight decks featuring GFC 700, plus our new, cost-effective GFC 500 and GFC 600 retrofit autopilots — along with several Garmin autopilot solutions for experimental and light sport aircraft.

    Ted Stanley
    West Tisbury

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