July 16, 1999
It was nearly 8:30 on this torrid Friday evening, and the sun was already sinking into the strange, yellowish haze that consumed the horizon. If he had left two hours earlier as originally planned, John F. Kennedy Jr. would have arrived at Martha’s Vineyard in time to see Gay Head’s majestic gray, white, and crimson clay cliffs standing in sharp relief against the darkening sky. Gliding over the cliffs, John and his two passengers in the Piper Saratoga—his wife, Carolyn Bessette, and Carolyn’s sister Lauren—would all have been treated to a gull’s-eye view of Red Gate Farm, the 474-acre estate that had been his mother Jacqueline’s true refuge—a Shangri-la of dunes, marshes, Scotch pines, and scrub oaks, bordered on one side by square-shaped Squibnocket Pond and on the other by 4,620 sandy white feet of private oceanfront.
Kennedy family friend George Plimpton called it “a dream place, a sunlit place. It’s hard to explain the effect it all had on you—all the variations in color, water sparkling like diamonds everywhere you looked.”
That had been the original plan—to leave Manhattan at 6:30 p.m. and be in the air by 7:15 so that John, who had yet to learn how to rely solely on his instruments, could fly under visual flight rules. John was accustomed to cutting things close, and given the Piper’s cruising speed of 180 miles per hour, leaving at 7:15 would put them safely on the ground at Martha’s Vineyard Airport well before nightfall. They would drop Lauren off with friends, and then make the quick hop over to Hyannis Port for the wedding of John’s cousin Rory—all before Cape Cod, the islands, and the ocean that separated them were engulfed in darkness.
Even if they had managed to leave on time and make it the Vineyard before sunset, Carolyn was far from enthusiastic about boarding a small plane with her husband alone at the controls. She was well aware of just how much her husband enjoyed pushing the envelope—like the time just a few years earlier when a group of John’s friends watched as he swam out to sea off the coast of Baja California and simply vanished. John’s terrified pals began to run for help when, as one recalled, “all of a sudden he just reappeared.” Then there were the kayaking trips in which John would take off alone for long stretches at a time and simply materialize at base camp, filthy, wrung out, and deliriously happy. John simply showed no sign of outgrowing his daredevil streak: Just that spring South Dakota authorities denied his request to rappel down the face of Mount Rushmore, the sort of stunt that prompted his closest friends to call him “Master of Disaster.”
It was a part of John’s personality that Carolyn’s celebrated mother-in-law took great pride in. Jackie made a point of indulging, even encouraging her son’s instinctive adventurous streak. Whether he was mountain climbing, scuba diving, playing football, skiing, or simply zipping in and out of midtown Manhattan traffic, Jackie was proud of her son’s unfettered athleticism. She did not even protest when he disappeared into the wilderness for as much as a week at a time.
John’s obsession with taking to the skies at the controls of his own plane was an entirely different matter.
“Please don’t do it,” she pleaded with John when she discovered he was pursuing his pilot’s license. “There have been too many deaths in the family already.” Given the Kennedys’ track record when it came to flying, Jackie clearly had a point. Joe Kennedy Jr., the eldest of John’s uncles, died when his plane exploded over the English Channel during World War II. Four years later, in 1948, John’s aunt, Kathleen “Kick” Kennedy, perished with her lover, Earl Fitzwilliam, when their plane crashed into France’s Cévennes Mountains.
John’s aunt Ethel lost both her parents in a 1955 plane crash, and her brother when his plane crashed eleven years later. In 1964, John’s uncle Ted was flying to Springfield, Massachusetts, in a storm to accept the Democratic nomination for a second U.S. Senate term when his small campaign plane crashed into an apple orchard. Both his aide and pilot were killed, but Ted managed to survive—albeit with a broken back. In 1973, John’s twenty-four-year-old stepbrother—Aristotle Onassis’s only son, Alexander—died when his plane crashed immediately after takeoff.
Jackie confided to Maurice Tempelsman, the wealthy diamond merchant who shared the last fifteen years of her life, that there was another reason for her concern. In recent years, she was experiencing a series of premonitions regarding both her children, and the strongest and most persistent of these involved John perishing at the controls of his own plane. She had made John swear that he would not pursue his pilot’s license, and on her deathbed in 1994 made Tempelsman and her brother-in-law Ted Kennedy swear that they would do whatever was necessary to keep him from becoming a licensed aviator.
John abided by his mother’s wishes during her lifetime, but by late 1997 he was enrolled in a Florida flight school. Although John took Tempelsman’s financial advice—Maurice had managed to parlay Jackie’s $26 million settlement from the estate of her late husband Aristotle Onassis into a $200 million fortune—John turned a deaf ear to Tempelsman’s pleas and warnings when it came to flying. The open sky, he tried to explain, was the only place where he felt truly liberated. “You know,” explained his college pal Richard Wiese, “it was just him up there, away from everybody and it made him feel free.”
Neither Tempelsman nor Uncle Teddy would fly with John alone at the controls, and while she told friends she would have loved to oblige her husband, Carolyn was equally reticent. In addition to John’s well-documented penchant for risk taking, Carolyn also worried about his lack of focus (John suffered from attention deficit disorder) and his chronic absentmindedness. John routinely misplaced things—his gloves, his credit cards, his wallet. It didn’t help that he kept his keys on a chain fastened to his belt loop; they still disappeared with frustrating regularity—so often that he kept a spare set of keys to their TriBeCa apartment tucked under the front stoop. This inability to concentrate for extended periods of time—something a pilot would obviously be required to do—was of particular concern to the meticulously organized Carolyn. “We spend hours every day just looking for his stuff,” she complained. “It drives me so crazy.”
More to the point, it had been only six weeks since John took to the skies over Red Gate Farm in a $14,300 Buckeye ultralight powered parachute—a flimsy contraption that resembled a go-cart with an engine-drive propeller at the back—and crashed, snapping his right ankle. Undaunted, and with his foot still in a cast, John flew back up to the Vineyard for the Fourth of July. This time, Carolyn agreed to go as John’s passenger—but only because there was a licensed instructor sitting next to him in the cockpit. Otherwise, she would buy a seat on one of the scheduled airline flights or drive the five hours to Hyannis and then take a ferry to the island. Once while she waited to meet John at the Martha’s Vineyard airport café, Carolyn told her waitress, Joan Ford, why she was reluctant to fly with John. “I don’t,” she said without hesitation, “trust him.”
On today’s trip up from New Jersey, Jay Biederman, the flight instructor who had recently helped John pass his written instrument test and was preparing him for his instrument flight test, was scheduled to go along as he had several times before. But when Biederman canceled to join his parents on a hiking trip in Switzerland, John made the fateful decision not to find a replacement.
Carolyn’s thirty-four-year-old investment banker sister harbored no reservations about John’s piloting skills. Lauren Bessette was a Wharton School graduate with a command of Mandarin Chinese, and a rising star at Morgan Stanley. She could be most persuasive. Over lunch at the Stanhope Hotel’s Café M that Wednesday, July 14, John was overheard enlisting Lauren’s help in talking his wife into going. “Oh, come on now,” Lauren urged Carolyn, “we’ll have fun.”
Kyle Bailey was also planning to fly to Martha’s Vineyard that night, but when he arrived at New Jersey’s Essex County Airport he could see that “something was not quite right.”
Instead of the clear five-to-ten-mile visibility being reported by the Federal Aviation Administration, an odd haze was blanketing the region. He picked out a fixed point on the horizon—a ridge he would normally be able to make out in the distance. “But I couldn’t see it at all,” Kyle said. “There was this really strange, thick haze. Heavy but sort of shimmering at the same time. It was already getting dark, and the wind was picking up. So I decided it wasn’t worth the risk.”
John made a different decision. Since the cast had been removed from his injured foot just twenty-four hours earlier, he hobbled to the plane on crutches, tossed them into the baggage compartment, then gingerly pulled himself up into the cockpit—all the while wincing in pain. Behind him, Carolyn and Lauren belted themselves into the Piper’s tan leather seats. They faced forward, with two empty rear-facing seats opposite them.
Now, as he walked to his car, something made Bailey turn around. “It was so spooky,” he said, “but I watched as they taxied into position and waited to be cleared for takeoff.” The aircraft’s registration number, N92539A, was emblazoned on its fuselage. Bailey noticed that this was different from the number on John’s older, less powerful Cessna. John was actually having that number, N529JK, transferred to the new plane. N529JK was a reference to his father’s May 29 birthday.
Bailey found himself standing, unable to move—“as if something was telling me it was important to keep watching.” Since Lauren was seated on the opposite side of the plane, Bailey could not see her. But as the Piper idled on the runway, John and Carolyn—she seated directly behind him and facing forward—were plainly visible in profile. “It was hazy but their silhouettes were so clear. I was struck at the time by how ethereal it looked, how eerie.”
There was no obligation to file an official flight plan that night, but John did inform the control tower at Essex County Airport that he intended to fly due north and then east to Martha’s Vineyard. Just twelve minutes after sundown, at 8:38 p.m., the tower cleared John for takeoff. He advanced the throttle, and the Piper Saratoga rolled down Runway 22. In a matter of seconds, the plane carrying JFK Jr., his wife, Carolyn, and sister-in-law Lauren Bessette lifted off the tarmac and sailed smoothly into the twilight sky—heading due south at first, over a golf course, then banking right before making a gentle turn toward the northeast. “North of Teterboro,” he told the control tower in his only radio communication that night.
“Eastward . . .”
Had he known about his new plane’s many remarkable capabilities, John could simply have pushed two buttons to activate the Piper Saratoga’s automatic pilot feature and it would have flown him all the way from New Jersey to Massachusetts. Once there, it would have even executed a perfect three-point landing at Martha’s Vineyard Airport.
If he was even aware that he could put his plane on automatic pilot, John gave no hint of it. “The Piper was his shiny new toy, and he was thrilled with it,” a friend said. “But it was an awful lot of plane to handle, and John was still learning the ropes.”
As it climbed at a speed of 104 miles per hour toward its cruising altitude of 5,600 feet, the plane crossed over the Hudson and headed toward Long Island Sound. It had been in the air only a matter of minutes when an air traffic controller on Long Island spotted an unexpected blip on his radar screen. A small plane of unknown origin—since John hadn’t filed a flight plan there was no way for anyone to know precisely who he was or where he was heading—seemed to be edging perilously close to an American Airlines passenger jet.
Alerted to the danger, the pilot of the airliner was taken aback by the sight of the Piper Saratoga emerging from the mist just off the tip of his right wing. Careful not to upset his 160 passengers, he made a subtle maneuver to put distance between his airliner and the smaller craft—and avert the midair collision that otherwise would have been inevitable.
Inside the Piper, everyone was blissfully unaware of how they had just cheated death—at least for the time being. To protect their ears from the earsplitting whine of the engines, John and the Bessette sisters wore headphones that made it possible for them to talk about their weekend plans and trade gossip about their wide circle of friends in New York as they leafed through fashion magazines spread out on the small foldout table between them.
John must have thought he was playing it safe at that point—never straying far from the Connecticut coastline, ticking off the names of the cities and towns as they appeared one by one just over his left shoulder: Greenwich, Bridgeport, New Haven, Old Saybrook, New London, Mystic.
He could make them out—just barely. But after forty minutes in the air, nothing was visible. The murk was now so dense that neither the comforting sight of the city lights below nor the stars above were available to help guide John on his way.
At any time, John could have pushed those two lifesaving buttons to turn on the automatic pilot. Dr. Bob Arnot, flying just twenty minutes ahead of Kennedy, considered doing just that. When he approached the Vineyard and searched for the lights of Oak Bluffs, Edgartown, and Vineyard Haven, Arnot saw nothing. “It’s as if someone put you in a closet and shut the door.” Arnot wondered if the island had suffered a power failure.
“There was no horizon and no light,” he said. “The night could best be described as inky black.”
At 9:24, John still had the option of simply pushing the two buttons that put his plane on autopilot. Now, forty-six minutes into his planned flight, John instead scanned the coastline for familiar landmarks as he flew over Westerly, Rhode Island.
Nothing.
Looking to the right, he searched for the hatchet-shaped outline of Block Island, but there was only darkness below.
Anyone flying strictly by visual flight rules and not relying solely on instruments would normally have borne left once he reached Point Judith and clung to the coastline until he reached Buzzards Bay. Then he could make a right turn and fly straight out to Martha’s Vineyard over eight miles of open water. Instead, John decided to maintain his course straight ahead to the Vineyard over thirty-five miles of ocean. This final leg of the trip would take only six minutes, but it meant that John would have no visual reference points, lights, or landmarks. Without them, local pilot Tom Freeman observed, “you are totally, completely in the dark—literally as well as figuratively—if you don’t know how to rely on your instruments. It’s a sickening, scary feeling.”
By this point, other pilots in the region were either radioing for assistance or asking for permission to put down at alternate airports inland until the fog lifted.
John, however, pressed on.
His first instinct, understandably, was to try to drop below the cloud layer. Fifty-six minutes after takeoff, at precisely 9:34 p.m., John pushed the yoke forward and with the airspeed indicator reading 150 knots (173 miles per hour), swiftly descended at the rate of 700 feet per minute. Leveling off at 2,300 feet, he was at last below the haze and could see Gay Head Lighthouse and, not far beyond, the lights of Jackie’s beloved Red Gate Farm.
But within five minutes, John was back to flying blind. Another pilot in the area that night describes the sensation as being in a room with the windows painted white. John’s instructors had warned him about spatial disorientation, and how, deprived of visual cues, the human brain can quickly confuse down with up and up with down. Even the most experienced pilots, he remembered being told, developed debilitating vertigo—and that was why, under these conditions, the only way to safely arrive at his destination was to rely solely on his instruments and ignore what his body was telling him.
In the cockpit, John tried to square what his body seemed to be saying with the readings on the gauges and dials directly in front of him. The off-kilter reading on the directional gyro in the lower center of the instrument panel would have contradicted whatever it was he was feeling. A quick glance at the turn-and-bank indicator in the lower left-hand corner would have shown that the red ball was not centered and that his wings were not level—no matter what his own senses were telling him.
His head swimming, John made a sharp right turn and took the plane back up three hundred feet—a last, frantic maneuver to somehow get above the haze. By this point John’s body was, in the words of veteran military pilot Edward Francis, “undoubtedly playing all sorts of tricks on him. You can be upside down and turning to the left and your body is telling you you’re right side up and turning right.” Add to this confusion the mounting panic of the two women behind him. “By now they would have been bounced around enough to know something was seriously wrong,” Francis speculated. “They may have been screaming. They certainly would have been asking John what was happening.”
Unfortunately, John had not yet gone through the phase of instrument training that might have helped him cope with pandemonium in the cockpit. In the air, instructors simulate an emergency and then try to rattle a novice any way they can—by yelling, grabbing at the controls, or even popping a paper bag—all to reinforce the pilot’s ability to ignore distractions and focus on the problem at hand. “They train you,” Kyle Bailey said, “to have nerves of steel.”
Still, John managed to level off at 2,600 feet and steer the plane straight for Martha’s Vineyard Airport, now just twenty miles ahead. He maintained this course for a full minute before he must have again begun listening to the mixed messages his senses and the instruments were sending him. At 9:40 p.m., John, clearly disoriented, turned south, away from the island. He then began to bring the plane down, descending gradually until the plane reached 2,200 feet. It was then that the Piper Saratoga suddenly surged downward at an alarming 5,000 feet per minute—ten times the normal airspeed.
Yet the situation was not hopeless—not yet. If he could just have maintained the presence of mind to level his wings before pulling up on the yoke, he could have regained altitude and saved the plane. To accomplish this, the notoriously absentminded John would have had to bring to bear all his powers of concentration, and he would have had to rely solely on his instruments. Instead, he made a classic—and fatal—mistake: pulling up on the yoke without bothering to level the plane. As a result, the Piper Saratoga started to turn clockwise in a corkscrew fashion, picking up speed as it headed downward in what aviators refer to as a “graveyard spiral.”
Inside the cabin, John, Carolyn, and Lauren were pressed back into their leather seats as the plane spun wildly toward the ocean’s surface at a rate of ninety-nine feet per second. They would no longer be able to scream; the G-forces pressing against their chests would have already forced the air out of their lungs. All they would have been able to do was listen in terror to the wail of the engine and the wind shrieking past the windows.
Listen, and wait.