Watching the immensely popular television series Love Story took me back to a strange week from my history. One afternoon in April of 1994, while I was working in a studio apartment that I had converted into an office, I received some devastating news from my wife: Cynthia Horner, a psychiatrist companion and co-tenant at the office, had passed away just before reaching her 30th year. Cynthia had recently relocated to live with her boyfriend, John Perry Barlow, a songwriter and a friend of mine. Barlow informed me that Cynthia had unexpectedly died on a plane due to a virus that had previously affected her heart. I rushed over to Barlow’s home, where he, another friend, and I spent hours in mourning. That friend, well-acquainted with tragedy, was John F. Kennedy Jr.
Barlow, who died in 2018 at the age of 70, was recognized for his contributions as a lyricist for the Grateful Dead, an advocate for the internet, and a co-founder of the Electronic Frontier Foundation. He was also a prominent figure during the early days of WIRED and was one of JFK Jr.’s closest pals, a detail he frequently discussed openly.
Their friendship began in 1977 when Jackie Kennedy asked Barlow, who was managing his family ranch in Wyoming, to welcome her 17-year-old son, JFK Jr., to experience ranch life. Barlow accepted, introducing Kennedy to ranch tasks enhanced by LSD, which resulted in a deep friendship.
Their connection endured for years. Barlow recounts a Prince concert he attended with Kennedy, both influenced once again, which energised the entire Radio City Music Hall to dance. Later, Barlow and Cynthia went on double dates with Kennedy and his then-girlfriend, Daryl Hannah, who played a key role in organizing Cynthia’s memorial. In 1994, Kennedy began dating Carolyn Bessette. Barlow grew close to Bessette and attended their wedding in 1996.
In his autobiography, Barlow speculates about the tragic plane crash involving Kennedy, proposing that Kennedy postponed his flight to draft a condolence email after Barlow’s mother’s passing. Barlow expresses regret that Kennedy didn’t follow his previous advice: “When you lose sight of the horizon don’t look for it. Just put your eyes on the instrument and believe it.”