Why is Trump picking a fight he can’t win with Taylor Swift?

Now they’ve really got bad blood.

Donald Trump’s recent social media missive, “I HATE TAYLOR SWIFT,” was a stupid escalation in a war that the former president can’t win. To put it simply, he needs to calm down. 

Swift is the biggest star in the world, boasting legions of loyal fans. So it’s worth asking: Why would Trump and his minions be so openly hostile to her? 

I have a theory: Trump and his supporters, more so than “normies,” are keenly aware of Swift’s power because they understand that politics is downstream from culture. Trump understands this, having parlayed his time as a reality TV star all the way to the presidency. 

To be sure, the vast majority of celebrity endorsements don’t amount to a hill of beans. But Swift is no average celeb. She is in a rarefied category, up there with Oprah Winfrey in her prime. 

What’s more, Swift has crossover appeal, ranging from her days as a country singer to her current era as a pop diva. And now that football season is back in full swing, anyone watching the NFL (the Chiefs are currently 2-0 and could be headed to another Super Bowl) will be greeted with shots of her arriving at the stadium and closeups of her celebrating every touchdown from a private box.

To make matters worse for Trump, Swift is all but immune to criticism and threats of boycotts. Young people, especially young women, identify with her on a visceral level in a way that cannot be quantified. If you’re the parent of a Swiftie, good luck telling your child that, for political reasons, they can’t listen to her music or go to her concerts.

Again, though, few celebrity endorsements matter these days, if they ever did. This is where I think Swift’s superpower as an endorser comes into play. 

Swift’s utility is not to persuade middle-aged adults to switch their votes. Her power lies in the millions of young women who have turned 18 in the four years since the 2020 election. Swift can convince them to register to vote and to vote early.

(As a macabre thought experiment, imagine how many Trump voters have died since 2020 and how many Swifties have turned 18 since then, and you’ll get the idea.)

We are already seeing reports that Swift’s endorsement of Vice President Harris sent hundreds of thousands of people to Vote.gov.

The 2024 election will be likely decided by just tens of thousands of voters in just three to five states. The margins will be very tight, and anything could make the difference between winning and losing. 

We can’t know the precise impact that Swift’s endorsement will have in the handful of states that matter. But here’s one data point: WiscNews reports that, “In the days following last Tuesday’s presidential debate and Taylor Swift’s endorsement of Kamala Harris, the number of new daily voter registrations in Wisconsin surged, according to data from the Wisconsin Elections Commission.”

Trump’s recent attack (and I’m willing to bet he could be baited into making more) is yet another way he is alienating potential voters — and augmenting Democratic voter turnout for a wide range of women, from suburban soccer moms who are already uneasy about Trump to the so-called “cat ladies” that Trump’s running mate, Sen. JD Vance (R-Ohio), has disparaged. 

Team Harris is already exploiting this opening. Take, for example, Harris’s running mate Gov. Tim Walz’s Instagram video wherein he mentions Swift, wears a friendship bracelet and references beating “the smallest man who ever lived” (one of the tracks on her last album).

Walz and Harris are speaking the Swifties’ language, just as Trump seems to be working overtime to alienate them. If Trump were actively trying to offend women, I’m not sure he’d do anything differently. 

When it comes to Trump’s attacks, Swift will no doubt just “shake it off” and declare that haters are gonna hate. Her die-hard fans, on the other hand, might just deliver a payback at the ballot box.

Matt K. Lewis is a columnist, podcaster and author of the books “Too Dumb to Fail” and “Filthy Rich Politicians.”