John Perry Barlow, JFK Jr., and a Night of Grief I Can’t Forget

look 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 had recently moved in with her boyfriend, the songwriter and cyberspace philosopher John Perry Barlow, who was a friend of mine. In the afternoon my wife called me with the shocking news that Cynthia, just shy of her 30th birthday, had died. I called Barlow, who told me that Cymthia had died suddenly on the plane. They were both suffering from a bad flu last week, and the virus was silently attacking her heart. I dropped everything and headed to Barlow’s place. For the next six hours, Barlow and I, along with another friend, cried, drank, and banged our heads in the wake of the unspeakable event. That friend was no stranger to tragedy. He was John F. Kennedy Jr.

Barlow, who died in 2018 at the age of 70, was known for many things. He was the self-described junior songwriter of the Grateful Dead, an evangelist of the Internet, a co-founder of the Electronic Frontier Foundation, and a networker nonpareil. One key figure in WIRED’s early days is not mentioned. He was one of 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-talker. Still, the pairing was charming and it said something about both parties.

The relationship began in the summer of 1977. Barlow was tending his family farm in Pinedale, Wyoming, when Jackie Kennedy called at the suggestion of a mutual friend. As Barlow wrote in his posthumously published autobiography, Mother American NightJackie wanted her 17-year-old son, JFK Jr., to get a taste of the rugged farm life. Barlow said yes in his recap, and augmented the teenagers’ farm work with LSD. Among the tasks he performed while delivering doses were long drives in Barlow’s truck and dropping explosives into gas wells. They became close and over the years Barlow became more of a friend than an abusive father.

It was a lifelong relationship. Barlow writes about attending a 1993 Prince concert with Kennedy where the two were once again stumbling. Kennedy felt the audience was too restrained and urged Barlow to get up and dance. As Barlow writes, everyone at Radio City Music Hall attended. Later, after Barlow meets Cynthia, the two double-date with Kennedy and his then-girlfriend, Daryl Hannah. After the night spent with Barlow and Kennedy, Hanna flew to New York and helped postmortem plan for a memorial service. She seemed like a lovely person.

In 1994, Kennedy moved on from Hannah and attracted the charismatic Carolyn Bessette. Barlow became a confidant to his friend’s new girlfriend – even being part of their intimate wedding ceremony in 1996. A photo shows Barlow preparing for the formalities with JFK Jr., Ted Kennedy, and a priest. I don’t know what Barlow said to honor the couple, but I imagine the songwriter who wrote “Estimated Prophet” would have had sharp words mixing humor and insight.

In Mother American NightBarlow offers an alternative explanation for why Kennedy’s Cessna took off at sunset, resulting in a night flight and the death of his wife and his sister, as well as the man himself. Barlow says she had just sent the news to her 2,500 closest friends that her mother had died. He says Kennedy was late to the airport because he was writing a long condolence email to Barlow. Leaving aside the reasons for the late takeoff, Barlow claims that he had previously given Kennedy a warning that was ultimately ignored: “When your sight leaves the horizon don’t look for it. Just keep your eyes on the instrument and trust it.”