SPRING 1973
“I don’t know about this,” twelve-year-old John Kennedy was telling his sister, Caroline. “When Mummy finds out, we’re gonna be in big trouble.” The siblings were standing out on a runway at Hanscom Field in Middlesex County, Massachusetts. A flight instructor named Matthew Johnston was standing before them, along with Lem Billings, the family friend who’d taken many of the next generation under his wing, particularly Bobby Jr.
Lately, fifteen-year-old Caroline Kennedy had become fascinated by the idea of flying. She loved looking at pictures of airplanes in magazines and had become fixated by the idea of soaring into the sky. It was one of those crazy ideas that would never amount to anything in the lives of most children. When she would mention it to her mother, Jackie would always say, “Absolutely not.” John had been talking about planes since he was three, and she wasn’t discouraging of it. However, Caroline was old enough to know better.
Undaunted by her mother’s disapproval, Caroline somehow coaxed Lem Billings into signing the permission forms that would allow her to just go up in an aircraft for a quick trial run experience. Why Lem would do this is anyone’s guess. He had to know Jackie would not approve. Some in the family would later say Lem probably felt that his best friend—Caroline’s late father, Jack—would have wanted his daughter to have the experience, even if just to get it out of her system. Instructor Johnston was ambivalent, though. Many years later, he recalled, “When I said I needed to get Jackie’s permission before I could take the kid up, Billings got aggressive with me. He said he was sure it was fine and for me to just let the papers he’d signed be sufficient. Against my better judgment, I said okay. I would just take her up for a quick flight, I told him, not an introductory lesson. In a formal intro, I would let the student actually fly the plane.”
“You guys wait here,” the instructor told John and Lem as he handed the boy a pair of binoculars. Johnston then helped Caroline into the passenger seat of the cockpit of a blue-and-white Cessna 172. He got into the pilot’s and, five minutes later, the plane was slowly pulling out onto the main runway. Caroline, beaming and waving at her brother through the window, was obviously excited. He waved back. Minutes later, the Cessna sped off and then was up … up … and away.
About a half hour later, Johnston finally brought the plane down. By this time, his young passenger’s eyes were as wide as saucers. Yes, Caroline said, she definitely wanted to take further instruction. “Me too,” John piped in. “Me too.” The flight instructor explained that John was too young; fifteen was the cutoff age. “I told him to wait a couple years and come back,” Johnston recalled. “He frowned at me. Then Caroline wondered how they would convince Jackie. Lem said, ‘Oh, just leave that to me.’ He was confident, but John wasn’t having it. He said that their mother would never let Caroline fly. ‘She’s going to be very cross with us for even coming here,’ he said. I remember thinking, That’s an odd thing for a kid to say—‘very cross.’ It sounded like something maybe he’d picked up from his mother.”
According to what the instructor recalled, Caroline knelt down to John’s level. Holding him by his slim shoulders and looking him straight in the eye, she said, “John, you can’t let people tell you what you can and cannot do,” she said.
“Even Mummy?” he asked, his eyes wide with surprise.
“Yes. Even Mummy.”
Matthew Johnston recalled, “As I watched, Caroline made them do a pinkie swear. She told her brother, ‘I promise to help you make all your dreams come true, and you have to promise to help me make all of mine come true—and that includes going up in this plane.’ They then locked their little fingers. ‘Okay, I promise,’ John said seriously.
“Lem didn’t like it at all,” said Johnston, “the part about them not allowing people to tell them what to do. ‘That is not right, you two,’ he said, glaring down at them. ‘It’s precisely because you are Kennedys that you have an obligation to your family and even to your country. This isn’t about your dreams, it’s about your obligations. You are old enough to know better. I never should have brought you here,’ he said angrily. He was all bent out of shape. ‘Now, let’s go,’ he demanded. Chastised, the two kids didn’t say a word. Lem then began walking quickly, and the siblings followed, holding hands, John tripping over his feet trying to keep up. Caroline turned and looked at me with a sad face and waved. I waved back.”
The next day, Matthew Johnston got a call from Rose and Joe Kennedy’s attorney Benedict F. Fitzgerald Jr. “From my understanding, Jackie called Rose, agitated about Caroline being taken up in a plane,” remembered Fitzgerald. “She didn’t know how to handle the situation because Mr. Billings, a trusted friend of the family’s, had been involved. She asked Rose what could be done about it. Rose called me to ask what I thought. I happened to be a licensed pilot. I had bought my first plane when I was a teenager. I also served as a pilot and flight instructor in the Navy. I taught [baseball stars] Ted Williams and Jimmy Piersall how to fly. Therefore, I understood flight instruction and was astonished that any licensed instructor would have taken Caroline up without parental authorization. I told Rose I would handle it.
“I then called the gentleman and had a reasonable if also firm conversation with him, telling him that the Kennedys were agitated because of what he’d done with Caroline. He was extremely apologetic. He asked if he should call Jackie to express regret. I told him I felt that would just make things worse, to just bow out at this point and never do such a thing again, not only with Caroline but with any adolescent without parental approval. I then reported back to Rose that I had taken care of it.
“The next day, Jackie called me and thanked me. ‘We cannot tempt fate in this family,’ she told me. ‘We’ve had enough tragedy. I will never let my children fly. Never.’”