Taylor Swift, Donald Trump, and the Universal Traits of American Iconography
In March 2013, The New York Times ran an article about Taylor Swift’s tumbling popularity. Beyond a few stray statistics, the Times had little evidence for such a declaration. Though the piece already seemed ridiculous upon publication, it’s deserving of outright mockery today—evidence that, even outside the political arena, the Times may not be all that removed from the tabloid rag its critics have long alleged.
Within two years of the article’s publication, Swift would finish a massively successful tour and dominate the Grammys with 1989. That album won her second Grammy for Album of Year before she eventually set a record in 2022 as the only artist in the history of music to earn the award four times. Swift has won so much that her fans should be sick and tired of her winning. But, 12 years later, her base is not only welcoming new constituencies but only increasing its fervor.
When Donald Trump secured the presidency a few hours after midnight on November 6th, I immediately flashed back to The New York Times’s Taylor misfire and the gloating pieces the paper of record ran when the president-elect was convicted of a felony last May. As a fan of Swift from her early days in Nashville, I’ve been frustrated for the last few years that she’s undercut her reputation as a nuanced artist with base political stunts like assuming the role of ultimate childless cat lady when endorsing Kamala Harris. But, like Taylor, Trump didn’t just mount a comeback; he somehow built on his hard-won status as the most influential politician of the 21st century with an inarguable political touchstone. He utterly 1989ed 2024 while succeeding Swift as Time’s Person of the Year.
Of course, Rolling Stone chief music critic and unabashed Swiftie Rob Sheffield doesn’t make this connection in his new book, Heartbreak Is The National Anthem: How Taylor Swift Reinvented Pop Music. In fact, he calls Swift’s decision to remain neutral in the 2016 election, “the dumbest mistake of her career.” However, in his well-argued deep dive into Swift’s cultural significance, he accidentally touches on the traits of American iconography that have catapulted both Taylor and Trump to their statuses as the two most influential figures in the American Pantheon since Bob Dylan and John F. Kennedy.
In his assessment of Swift’s appeal, Sheffield sees 1989 as her watershed moment because it marked a definitive break from country music. Except, as he acknowledges, it really didn’t. Swift continues to offer glimmers of her country roots both in the songs on stripped-down records like Evermore and half of last year’s The Tortured Poets Department as well as in her pioneering decision to re-record her back catalog after her arch nemesis, Scooter Braun, bought it in 2019 from her former label.
Citing his favorite song from Taylor’s pivotal era, Sheffield writes, “To be a New Romantic is to be always leaving Nashville.” However, one should not take Sheffield’s metaphor as an update of “big fish, small pond” cliches. As he argues throughout the book, Swift could have had an easy career cranking out intimate country ballads for a few years before moving into non-Music Row endeavors when the formula got stale like Jana Kramer and Kellie Pickler before her. Instead, she opted to expand her Empire. For Sheffield, re-recording her entire catalog was the equivalent of making a play for Greenland or moving the embassy to Jerusalem—an outlandish plan that elicited mockery before becoming the most revolutionary act the music industry has seen in decades.
Though Swift and Trump started out as celebrities who occasionally ran in the same circles and share a contentious relationship with Kanye and Kim, what has kept them both at the center of America’s pop and political culture for the last decade has been their willingness to unapologetically stick to their visions. Sheffield remarks that, by 2010, Swift had learned to “Work the room in a way that might be more like political candidates than other singers.” What this analysis misses is that Swift, like Trump, honed such skills in her formidable years only to master how to fly in the face of the staus quo.
Last spring, as pundits on both sides urged Trump to calm down and stick to policy, music critics second-guessed Swift’s decision to immediately release an additional album of content the night that Tortured Poets dropped. Regardless, her Eras Tour and record sales, like Trump’s campaign, continued to thrive. In the words of Sheffield, Swift “will hang a lantern on a nonstory that would blow over in minutes if she just turned off her phone,” an assessment that even the most MAGA faithful routinely admit is their leader’s primary flaw. Yet, not even the duo’s greatest missteps and most petty moments can eclipse what, to their bases, is the 21st-century iteration of the contrarian spunk that the greatest Americans have always adopted.
In two weeks, we all will gain a more accurate picture of how Trump’s latest act will shape his legacy. At the end of her Eras tour and nearly a year after her last record, Taylor’s next epoch should be readily apparent by the end of 2025. Whether she will emerge as a vocal Trump critic or go back to doing her own thing remains murky.
But, even the most deranged never Trumper knows that their boogeyman has a knack for knocking off his opponents—either through outright annihilation like Don Lemon, Hillary, Kamala, and Justin Trudeau or through reconciling the bad blood ala Megyn Kelly and Joe Rogan. Like Trump, Swift has also never lost a battle, as Kanye, Braun, and Katy Perry can attest, thanks to her talent for self-professed “vigilante shit.” If such a matchup does occur, it will not be an ill-conceived publicity stunt ala Tyson-Paul, but a showcase of the last vestiges of an American Exceptionalism that those with lesser achievements would like to pretend no longer exist.
Heartbreak Is The National Anthem is now available where books are sold.