‘Wave That Flag’: Meet the Deadheads Who Stump for Trump

Noah Eckstein
·6 min read
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On the lawn of Jeff Whritenour’s house in Kinnelon, New Jersey, a sign reads, “Presidents are temporary, the Grateful Dead is forever.” A few feet away, a flag bearing the iconography of the Grateful Dead flies above a Trump 2020 banner. Passersby often pause for a double-take, no doubt questioning what many would perceive as conflicting messages. After all, the Dead were liberal, pot-smoking hippies of the San Francisco counterculture; musicians inspired by the LSD experience of the 1960s and the Beat Generation. These attributes aren’t what naturally comes to mind when thinking of Donald Trump’s supporters but Whritenour doesn’t see it that way.

“I’m not a big fan of the president, but at the end of the day, Trump is about individual freedom and so was the Dead,” says the insurance claims consultant. His take, along with that of an unknown number of Trump-supporting Deadheads, is that the Grateful Dead’s philosophy was about individual liberties and not telling people what to do.

“I ain’t buyin’ it,” declares Dennis McNally, the Grateful Dead’s longtime publicist and author of “A Long Strange Trip: The Inside History of the Grateful Dead.” McNally worked for the band from 1984 to 2004 and feels that the essence of the Grateful Dead’s music — and its core members Jerry Garcia, Bob Weir, Phil Lesh, Mickey Hart and Bill Kreutzmann — is to be compassionate and tolerant. “The capacity for people to compartmentalize their lives is infinite, and anyone who is serious about being a Deadhead and then supports Trump is more or less consciously overlooking the values that he espouses which are bigotry and cruelty.”

The Dead’s lyrics are not a polemic, there is a lot of room for interpretation and disparate perceptions. Further, it’s difficult to identify a singular theme or collective Grateful Dead political philosophy. Most of their lyrics were written by Robert Hunter, a poet inspired by folk music whose words elicited no mundane meanings but rather formed an authentic journey into an old, ideal, adventurous storybook America. The Dead saw themselves as meta-political, playing concerts at anti-war protests but never supporting any political candidates. In fact, it’s rare that an original song by the Dead even reference a news event of its time. The Dead have no “Ohio” in their repertoire.

That political agnosticism may in fact be what draws Republicans and libertarians to the band. Deroy Murdock, a political commentator and Fox News contributor, saw the Dead over 70 times and uses the song ‘Liberty’ — specifically Hunter’s lyric “to find my own way home” — as evidence that the Dead’s values are inherently conservative. Murdock attended Dead shows in the ’80s and ’90s with other rightist commentators like Ann Coulter and Marc Caputo. “The emphasis of individuality, self-expression, and patriotism is appealing to Trump supporters,” says Murdock, who prefers to focus on the president’s policy record rather than his public demeanor. Yet, after over four years of nonstop coverage, late-night tweet storms, and questionable leadership, it’s hard not to focus on Trump’s character. Murdock thinks that Garcia, the Dead’s somewhat reluctant leader, and Hunter would have found Trump amusing. “They would have laughed at his antics.”

“Actually, Hunter is spinning in his grave,” says McNally, who worked closely with the late lyricist and Garcia. Steve Silberman, a New York Times best-selling author who co-produced “So Many Roads,” a boxset of Grateful Dead music, says of Garcia: “Could you imagine Jerry supporting a government kidnapping 500 children and losing their parents? I can’t.”

This isn’t to say the band never took a political stance. In the summer of 1989, members of the Dead testified before Congress to raise awareness of deforestation in Malaysia. Garcia lit a cigarette in the non-smoking chamber before Representative Claudine Schneider, a Republican from Rhode Island, stated that her guess would be 90% of Deadheads did not vote. Garcia himself rarely voted, except as Silberman recounts, for Lyndon B. Johnson over Barry Goldwater in 1964. A few years later in 1993, Garcia stood in the oval office wearing sweatpants and sneakers as Vice President Al Gore explained the origins of the Resolute Desk, wearing a three-piece suit. “We would have never gone to the White House if a Republican was in office,” says McNally.

Garcia’s small acts of rebellion were indicative of a Grateful Dead philosophy that put great stock in freedom, autonomy, independence and not preaching to the population. Still his reasoning for being invested in the rainforest issue was: “I am an earthling on this planet,” pointing toward a spirit of caring that is at the core of the Dead’s philosophy.

“Conservative Deadheads have gotten much more stupid and much more programmed,” says Silberman, who fears civil war may be imminent with potential polling place violence on election day and Trump’s continued spread of Covid-19-related misinformation. He, like countless others quarantined in their homes for months, has found himself returning to the comfort music of his youth, turning to the Dead’s melodies and sense of community “for something more meaningful, as a place to be reborn at every show.”

But Silberman also recalls shows in the ’70s and ’80s where he felt afraid to hold his boyfriend’s hand in public, worried about being “gay-bashed” by those in attendance. “Homophobia and sexism ran in the Grateful Dead family,” he says.

Murdock, who is a Black gay man, insists that the scene was inclusive. He also feels strongly that Trump is not a racist. “If he were racist, he would not have ended mass incarceration,” states Murdock, falsely, according to the American Civil Liberties Union.

The issue at the heart of conservative Deadheads’ point of view is the desire for little to no government interference in their private lives. Offers Whritenour: “We shouldn’t focus on Trump the man, but instead the right to do what I want with my time, money, and life.”

North Carolina newspaper editor Brian Clary, who attended Dead shows in the ’80s and ’90s, counters that the peace and love vibe “does not square with Trump… at all.” If anything, he believes Trump-supporting Deadheads are misinterpreting the songs and the culture. “The ‘I got mine, you got yours’ philosophy that [Trump’s] supporters are all about is the antithesis of the Grateful Dead.”

Among the Dead’s guiding mantras is Garcia’s oft-sung line, “Wake up to find out that you are the eyes of the world.” And while Deadheads may not collectively agree on the greatest “Dark Star” jam or who was the band’s best keyboardist, never mind politics, fans from all walks of life would endorse the fact that American has the right — and duty — to make their own decision on election day.

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