Watching the wildly popular television series Love Story took me back to a strange week in my past. One day in April 1994, I was working in a studio apartment that I used as an office. I split the cost with Cynthia Horner, a psychiatrist who’d recently moved out to live with her boyfriend, the songwriter and cyberspace philosopher John Perry Barlow, who was a friend of mine. Late in the afternoon my wife called me with the shocking news that Cynthia, just shy of her 30th birthday, was dead. I called Barlow, who told me that Cymthia had passed away suddenly on a plane. Both of them had suffered from a bad flu the previous week, and the virus had been silently attacking her heart. I dropped everything and headed to Barlow’s place. For the next six hours, Barlow and I cried, drank, and head-banged in the wake of the inexplicable, along with another friend. That friend was no stranger to tragedy. He was John F. Kennedy Jr.

Barlow, who died in 2018 at age 70, was known for many things. He was the self-described junior lyricist of the Grateful Dead, a proselytizer of the Internet, cofounder of the Electronic Frontier Foundation, and a networker nonpareil. Not to mention a key figure in WIRED’s early days. He was also among the closest friends of the so-called American prince, the son of our martyred president. The friendship was no secret—Barlow was an inveterate name-dropper. Still, the pairing was fascinating and said something about both parties.

The connection began in the summer of 1977. Barlow was tending his family ranch in Pinedale, Wyoming, when Jackie Kennedy called at the suggestion of a mutual friend. As Barlow wrote in his posthumously published autobiography, Mother American Night, Jackie wanted her 17-year-old son, JFK Jr., to get a taste of rugged ranch life. Barlow, in his retelling, said yes, and augmented the teen’s ranch chores with LSD. Things they did while dosing included long drives in Barlow’s truck and dropping explosives down gas wells. They became close, and over the years Barlow moved from a reprobate father figure to more of a friend.

It was a lifelong connection. Barlow writes of attending a 1993 Prince concert with Kennedy where both were once again tripping. Kennedy felt that the audience was too restrained, and he urged Barlow to get up and dance. As Barlow writes, all of Radio City Music Hall joined in. Later, after Barlow met Cynthia, the two would double-date with Kennedy and his then-girlfriend, Daryl Hannah. After the night I spent with Barlow and Kennedy, Hannah flew to New York and helped in the postmortem planning for a memorial service. She seemed to be a lovely person.

In 1994, Kennedy moved on from Hannah and wooed the charismatic Carolyn Bessette. Barlow became a confidant of his friend’s new sweetheart—even becoming part of the ceremony at their intimate wedding in 1996. One picture shows Barlow preparing for the formalities with JFK Jr., Ted Kennedy, and the priest. I don’t know what Barlow said to honor the couple, but I’d imagine the lyricist who wrote “Estimated Prophet” delivered trenchant words blending comedy and insight.

In Mother American Night, Barlow provides an alternate explanation for why Kennedy’s Cessna took off at sunset, resulting in a night flight that culminated in the man’s death, along with the deaths of his wife and her sister. Barlow says that he had just sent his 2,500 closest friends the news that his mother had died. Kennedy, he says, was late to the airport because he was composing a long condolence email to Barlow. Reasons for the late takeoff aside, Barlow claims that he had previously given Kennedy a warning that was ultimately ignored: “When you lose sight of the horizon don’t look for it. Just put your eyes on the instrument and believe it.”