Pretty much immediately after the US presidential debate last night between Vice President Kamala Harris and Donald Trump, Taylor Swift finally entered the chat. She made it clear who she’s voting for, and it’s who most of her fans believed she would vote for given her previous positions on the major issues at the forefront of this election. 

 

Madam Vice President has Taylor’s vote. 

 

Right off the top, Taylor mentions the debate – but it’s unlikely that she would have written it right after the debate. Tree Paine would never. This was locked and loaded, waiting to be fired. So the question is… 

Was the timing to, at long last, confirm Taylor’s endorsement always intended to be on debate night? Did the events and headlines of the preceding days have anything to do with it? That’s the gossip I want to focus on in this post. 

Over the last couple of weeks, Taylor’s friendship with Brittany Mahomes has been under scrutiny. Brittany’s behaviour on social media suggests that she’s MAGA and Swifties were becoming more and more agitated about her and Taylor’s ongoing closeness. Especially after their PDA at the US Open – because of course Taylor and her team would have been aware of the fans’ concerns and even criticisms. Let’s not pretend that Taylor hasn’t always been very online and deeply conscious about what her base is saying and how they’re reacting to her every move. 

 

It's not just the friendship that people were side-eying, because there’s a case to be made that Taylor can’t be expected to cut off everyone who disagrees with her politics, especially since this is the wife of her boyfriend’s best friend and colleague. But the issue was that Taylor was consistently seen in the company of someone who seems to support ideas that are doing real harm to many of Taylor’s fans, ideas antithetical to what Taylor has claimed to care about (reproductive rights, 2SLGBTQ+ rights, racial justice, and more) without reaffirming her position on these issues. As Daniel D’Addario wrote in Variety the other day: 

“Given, though, how much mileage Swift got in the past out of her decision to speak out on politics, the idea that she will remain silent would seem to make her past speaking out, at a more convenient moment, appear cynical. It’d be regrettable if her engagement with the world of politics were just another of her eras, and one from which she were willing to move on.”

Over at our Substack, The Squawk, our community has been having thoughtful conversations about Taylor’s silence as many of her fans – and there are a lot of Swifties at The Squawk, what’s up! – shared their expectations and sometimes disappointment over what they perceived to be Taylor’s unwillingness to take a stand against hate, bigotry, and oppression. One Squawk member talked about their adolescent children who are queer and who, over the last couple of weeks, have felt betrayed by the artist that they’ve been riding with their entire young lives. This pain, for them, is very real. 

 

So to go back to the question of strategy and timing, did this Brittany Mahomes mess have any impact on when Taylor chose to announce her endorsement? Or was this the plan all along? We know her to be thoughtful and precise. We know that she’s deliberate about what she says and when she says it. The MTV VMAs are happening tonight, Taylor is this year’s most-nominated artist so going into the event, we’re bracing for another trophy haul. Was she always intending to show up at the VMAs even more of a heatscore with all this political attention on her? Or did the developments of the last few days, as her fans’ uncertainty about her political positions got louder and louder, result in an audible and her endorsement following the debate? 

But also, what if the Vice President had flopped? Of course, considering she was up against that lazy f-ck, and given how she hard she worked and prepared, the probability of that was low… but it’s not impossible, because that man is a master of chaos, and it’s actually, unfortunately, derailment, distraction, and disturbance are his super powers. It would be a mistake not to guard against it. There was no guarantee that VP Harris would win the debate, had to earn her victory last night, both in the days before during her planning sessions and in the moment by staying present and picking and choosing her moments. 

 

I’m not convinced that Taylor and Tree were always intending for her endorsement post to go up right after the debate. Had the VP not outperformed her opponent, I would imagine Taylor’s advisors, the ones who have never wanted her to get involved politically, would have strongly pleaded with her that it would not be the right move at the right time. 

But I really WANT to believe that debate night was always circled on the calendar. Because if this was always the intention, it would indicate that Taylor understood the risk, understood the challenge facing the Vice President but at the same time was confident that she would be up for the task, so confident in VP Harris’s abilities that she knew the endorsement would come at the perfect time. With social media popping off about the debate, the Vice President landing the blows she needed to land, her opponent against the ropes, and Taylor coming in with the most anticipated and awaited celebrity endorsement to finish him off. At least on this night. That’s the version of events I want to believe. 

Join us at The Squawk today to discuss! (app link here)