Reflections on Loss: A Night with JFK Jr. and John Perry Barlow

Remembering a Night to Forget

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 shared this space 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 shocking news: Cynthia, just shy of her 30th birthday, was dead. I called Barlow, who told me that Cynthia had passed away suddenly on a plane. They had both 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 apartment. For the next six hours, Barlow and I cried, drank, and head-banged in the wake of the inexplicable, alongside another friend who was no stranger to tragedy—John F. Kennedy Jr.

The Bond Between Barlow and Kennedy

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, he was a key figure in WIRED's early days. His friendship with the so-called American prince, JFK Jr., was widely known. Barlow's revelations about this connection were as intriguing as they were revealing.

“Jackie wanted her 17-year-old son, JFK Jr., to get a taste of rugged ranch life.”

Their connection began in the summer of 1977 when Jackie Kennedy reached out to Barlow at the suggestion of a mutual friend. As Barlow recounted in his posthumously published autobiography, Mother American Night, he agreed to host JFK Jr. on his family ranch in Pinedale, Wyoming. Barlow augmented the teen's ranch chores with LSD, turning mundane tasks into memorable experiences that included not only driving around but also dropping explosives down gas wells. This pairing provided a backdrop that mirrored their evolving relationship—from a reprobate father figure to a genuine friendship.

A Lifelong Friendship

It was a connection that lasted a lifetime. Barlow recounted attending a 1993 Prince concert with Kennedy where both were caught up in the moment, urged by Kennedy to dance as the audience joined in. They were an inseparable duo, even during more intimate settings—after Barlow met Cynthia, they would often double-date with Kennedy and his then-girlfriend, Daryl Hannah.

After my night of grief with Barlow, I remember seeing Hannah in the aftermath as she flew to New York to help organize the memorial service. She seemed genuinely lovely and provided a comforting presence for a family struck by tragedy.

Moments that Shaped Their Lives

In 1994, Kennedy found love with Carolyn Bessette, and Barlow became a confidant for his friend's new sweetheart, even playing a part in their 1996 wedding. One memorable photo captures Barlow preparing for the formalities alongside JFK Jr., Ted Kennedy, and the officiant. Though I can only surmise what Barlow shared during that ceremony, I can imagine his heartfelt blend of humor and wisdom taken from his experiences as a lyricist.

“When you lose sight of the horizon, don't look for it. Just put your eyes on the instrument and believe it.”

During the tragic event that sealed their friendship in history, Barlow reflects on how Kennedy's final flight was influenced by personal tragedy. The decision to embark on that journey was clouded by grief as he composed a condolence email to Barlow after losing his own mother. Despite Barlow advising Kennedy about the risks of flying at twilight, he insists the warning went unheeded.

Reflections on a Shared Grief

I have a further anecdote about the depth of Barlow and Kennedy's friendship. During our impromptu grieving session, my wife called Barlow's apartment. JFK Jr. answered the call, and amid expressing condolences, she confused him for Barlow. “No,” he corrected her, ”It's John Kennedy.” He discreetly passed the phone to Barlow, who—sitting at Kennedy's feet—was greeted with, “John, how are you?”

Barlow's response was a snort of laughter. “Well aside from that, Mrs. Kennedy, how did you like Dallas?” Despite the immense grief surrounding us, this spontaneous moment provided levity that lightened an otherwise heavy atmosphere.

Longing for Their Presence

As I reflect on this episode, I couldn't help but recall these poignant stories while watching the recent portrayal of Kennedy's story. While I believe the television adaptation tried its best, it perhaps lacked some of the spirit and raw honesty that Barlow brought to the table. The world is undeniably poorer without their presence—both Barlow and Kennedy have left a meaningful void, one that many of us still feel deeply.

In sharing these memories, I aim to remind us all of the enduring connections that shape our lives, even amid the complexities of friendship and loss. Just like so many, I miss Barlow, Kennedy, and Bessette, whose lives were intertwined in ways that were both profound and human.