The saga between Donald Trump and Taylor Swift came to an unexpected head over the weekend when the former president and Republican candidate in the upcoming US election abruptly declared he “hates” the Grammy-winning singer.

No, we can’t believe this is the timeline we’re living in either.

How exactly did we reach this point? Well, here’s a brief history of how things between a reality-star-turned-world-leader and country-singer-turned-pop-juggernaut turned sour…

October 2012: Trump thinks Taylor Swift is ‘terrific’

Back when he was still mostly associated with his reality show The Apprentice and occasional rambling tweets (as they were still then known), the first time Trump ever appeared to acknowledge Taylor publicly was on social media.

Reacting to the news that the singer would be co-presenting the Grammys nomination broadcast for the following year, he wrote that he was “glad to hear it”, hailing the singer-songwriter as “terrific”.

Taylor had released her Red album just days earlier, securing an Album Of The Year nomination at the Grammys in 2014.

January 2017: Taylor Swift’s message of support for the Women’s March does not go down well

Taylor took a lot of heat during the 2016 election cycle for remaining silent when it came to politics, despite her massive platform (this included failing, for many years, to condemn the Neo-Nazis, far-right extremists and white supremacists who publicly hailed her as an “Aryan goddess”).

Coinciding with Trump’s inauguration in January 2017, demonstrations took place all over the world known as Women’s Marches, condemning the election of a newly-elected president who had made a number of misogynistic comments in the past, both publicly and privately.

“So much love, pride, and respect for those who marched. I’m proud to be a woman today, and every day,” she wrote on the site then still known as Twitter.

However, severalnews outletsnoted at the time that many fans were unhappy with Taylor for supporting the demo when she’d previously been silent on political matters all the way through the election.

This post has since been removed from Taylor’s account.

March 2018: Taylor voices support for the March For Our Lives demonstrations

Many entertainmentcommentators have hailed March 2018 as a turning point when it came to Taylor’s politics, after she shared a post in support of the March For Our Lives, a student-led demonstration calling for more gun control and reform of the legislation in the US around firearms.

“No one should have to go to school in fear of gun violence. Or to a nightclub. Or to a concert. Or to a movie theatre. Or to their place of worship,” Taylor wrote on Instagram.

“I’ve made a donation to show my support for the students, for the March For Our Lives campaign, for everyone affected by these tragedies, and to support gun reform. I’m so moved by the Parkland High School students, faculty, by all families and friends of victims who have spoken out, trying to prevent this from happening again.”

October 2018: Trump is unhappy after Taylor’s first ever political endorsement

For the first time in her career, Taylor publicly endorsed the Democratic candidate Phil Bredesen in her home state of Tennessee in the race to be made senator.

“In the past I’ve been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now,” she wrote on Instagram at the time, alluding to Trump’s time in office.

“I always have and always will cast my vote based on which candidate will protect and fight for the human rights I believe we all deserve in this country.”

Taylor added: “I believe in the fight for LGBTQ rights, and that any form of discrimination based on sexual orientation or gender is WRONG. I believe that the systemic racism we still see in this country towards people of colour is terrifying, sickening and prevalent.

“I cannot vote for someone who will not be willing to fight for dignity for ALL Americans, no matter their skin color, gender or who they love.”

She also condemned Bredesen’s opponent Marsha Blackburn, claiming her voting record in congress “appalls and terrifies me”.

“Please, please educate yourself on the candidates running in your state and vote based on who most closely represents your values. For a lot of us, we may never find a candidate or party with whom we agree 100% on every issue, but we have to vote anyway,” she urged her followers.

By way of response, Trump told reporters: “Let’s say that I like Taylor’s music about 25% less now, OK?”

In the end Marsha Blackburn – who would later be described by Taylor as “Trump in a wig” in her 2020 documentary Miss Americana – came out on top over Phil Bredesen in the Tennessee vote, despite the star’s efforts.

March 2019: Taylor says she’s “still finding my voice” when it comes to politics

Addressing her past silence in a letter with Elle to coincide with her 30th birthday, Taylor wrote: “I took a lot of time educating myself on the political system and the branches of government that are signing off on bills that affect our day-to-day life.

“I saw so many issues that put our most vulnerable citizens at risk, and felt like I had to speak up to try and help make a change. Only as someone approaching 30 did I feel informed enough to speak about it to my 114 million followers.”

Taking a not-so-subtle swipe at the then-president, Taylor continued: “Invoking racism and provoking fear through thinly veiled messaging is not what I want from our leaders, and I realised that it actually is my responsibility to use my influence against that disgusting rhetoric. I’m going to do more to help.”

“We have a big race coming up next year,” she added, referring to the then-forthcoming US election.

August 2019: Taylor makes a more explicit dig at Trump during an interview with The Guardian

“The thing I can’t get over right now is gaslighting the American public into being like, ‘If you hate the president, you hate America’,” she told the newspaper.

“We’re a democracy – at least, we’re supposed to be – where you’re allowed to disagree, dissent, debate.”

Not mentioning Trump’s name, she added: “I really think that he thinks this is an autocracy.”

The singer reiterated: “I just wanna do everything I can for 2020. I wanna figure out exactly how I can help, what are the most effective ways to help. ’Cause this is just… This is not it.”

She added she’d been “blindsided” by Trump’s victory in the election, claiming: “I was living in this Obama eight-year paradise of, you go, you cast your vote, the person you vote for wins, everyone’s happy!”

January 2020: Taylor ‘doesn’t care’ if Trump ‘comes after her’ due to her politics

The most revealing parts of Taylor’s documentary Miss Americana – which mostly charted her Reputation tour and the making of her seventh album Lover – came when she discussed her plans to maker her first political endorsement with her team, including her dad.

During the documentary, someone off screen suggests that potential headlines could read: “Taylor Swift comes out against Donald Trump”.

“I don’t care if they write that,” she insisted. “I am sad that I didn’t two years ago, but I can’t change that. I am saying right now that this is something that I know is right.”

“The president could come after you,” she is also warned by her publicist, to which she remarked: “Yeah, fuck that. I don’t care.”

May 2020: Taylor Swift warns Donald Trump: ‘We will vote you out’

At a time of unrest following the murder of George Floyd by a US police officer, Taylor Swift voiced her fury at Trump’s reaction to the global outcry. 

“After stoking the fires of white supremacy and racism your entire presidency, you have the nerve to feign moral superiority before threatening violence?” she questioned, insisting: “We will vote you out in November.”

August 2020: Taylor Swift comes out swinging against Trump once again

Three months later, Taylor explicitly called out Trump for a second time, accusing him of a “calculated dismantling” of the US Postal Service.

“He’s chosen to blatantly cheat and put millions of Americans’ lives at risk in an effort to hold on to power,” she fumed.

“Donald Trump’s ineffective leadership gravely worsened the crisis that we are in and he is now taking advantage of it to subvert and destroy our right to vote and vote safely. Request a ballot early. Vote early.”

This came days after she celebrated the news that Kamala Harris had been selected as Joe Biden’s running mate.

October 2020: Taylor endorses Trump’s opponent Joe Biden in the US election

Just shy of 14 years to the day after releasing her debut album at the age of 16, Taylor Swift made her first ever endorsement in a US presidential election in 2020.

She told V magazine a month before America went to the polls: “The change we need most is to elect a president who recognises that people of colour deserve to feel safe and represented, that women deserve the right to choose what happens to their bodies, and that the LGBTQIA+ community deserves to be acknowledged and included.

“Everyone deserves a government that takes global health risks seriously and puts the lives of its people first. The only way we can begin to make things better is to choose leaders who are willing to face these issues and find ways to work through them.”

She continued: “I will proudly vote for Joe Biden and Kamala Harris in this year’s presidential election. Under their leadership, I believe America has a chance to start the healing process it so desperately needs.”

February 2024: Trump claims Taylor wouldn’t endorse Biden again because ‘I made her so much money’

Back when it still looked like Trump and Biden would be going head-to-head for the second time in the 2024 presidential race, the former unfoundedly claimed that Taylor would never endorse the latter for a second time.

“I signed and was responsible for the Music Modernization Act for Taylor Swift and all other musical artists,” Trump claimed on his social media site Truth Social.

“Joe Biden didn’t do anything for Taylor, and never will. There’s no way she could endorse crooked Joe Biden, the worst and most corrupt president in the history of our country, and be disloyal to the man who made her so much money.”

August 2024: Trump falls for fake AI-generated ‘Swifties for Trump’ images

After what has so far been a bumpy election campaign (to say the least) Trump appeared to have seen fake AI-generated images of Taylor Swift and her fans endorsing him and believed them to be the real thing, even going as far as reposting them on Truth Social alongside the message: “I accept!”

In fact, the fake Taylor photo was originally created as a pro-Biden image last year, before apparently being adopted by Trump supporters.

“I don’t know anything about them other than somebody else generated them. I didn’t generate them,” she claimed. “These were all made up by other people. AI is always very dangerous in that way.”

September 2024: Taylor Swift discreetly shuts down Brittany Mahomes feud claims

This past year, Taylor has been a mainstay at Kansas City Chiefs games, where she’s shown up to support her boyfriend Travis Kelce. During this period, she appears to have started up a friendship with Brittany Mahomes, who is married to Travis’ teammate Patrick Mahomes.

Recently, Brittany found herself at the centre of controversy when she liked an Instagram post of Trump’s about his plans as the Republican party’s presidential candidate.

These included “keeping MEN out of women’s sport” and “carrying out the largest deportation operation in American history”.

Brittany later unliked the post, writing on her Instagram post: “I mean honestly, to be a hater as an adult, you have to have some deep rooted issues you refuse to heal from childhood. There’s no reason your brain is fully developed and you hate to see others doing well.”

Days later, she shared an additional post from a popular evangelist, which read: “Contrary to the tone of the world today… You can disagree with someone, and still love them. You can have differing views, and still be kind.”

Trump later thanked Brittany for what he claimed was “strongly defending” him on social media.

When the American football season started up again, people spotted that Taylor and Brittany were sitting separately, prompting speculation the latter’s controversy had led the singer to cool off their friendship.

Days later, she poured water on this speculation when she and Brittany were seen hugging in the stands of the US Open.

September 2024: Taylor Swift endorses Kamala Harris to be US president

While some pondered if this meant Taylor Swift would not be endorsing a candidate in the US election, she voiced her support for Kamala Harris immediately after the first debate between the Democratic candidate and Trump aired on US television.

“I will be casting my vote for Kamala Harris and Tim Walz in the 2024 Presidential Election. I’m voting for [Harris] because she fights for the rights and causes I believe need a warrior to champion them,” she wrote.

“I think she is a steady-handed, gifted leader and I believe we can accomplish so much more in this country if we are led by calm and not chaos. I was so heartened and impressed by her selection of running mate [Tim Walz], who has been standing up for LGBTQ+ rights, IVF, and a woman’s right to her own body for decades.”

Taylor added: “I’ve done my research, and I’ve made my choice. Your research is all yours to do, and the choice is yours to make. I also want to say, especially to first time voters: Remember that in order to vote, you have to be registered! I also find it’s much easier to vote early. I’ll link where to register and find early voting dates and info in my story.”

She signed off the message as a “childless cat lady”, an obvious dig at Trump’s running mate JD Vance’s widely-derided comments from three years ago. 

The record-breaking performer also shared that the AI debacle led to her speaking out.

“It really conjured up my fears around AI, and the dangers of spreading misinformation. It brought me to the conclusion that I need to be very transparent about my actual plans for this election as a voter. The simplest way to combat misinformation is with the truth,” she claimed.

September 2024: Trump reacts to Taylor Swift’s endorsement of Kamala Harris

“I was not a Taylor Swift fan,” Trump claimed the following day. “It was just a question of time. You couldn’t possibly endorse Biden. But she’s a very liberal person, she seems to always endorse a Democrat – and she’ll probably pay a price for it in the marketplace.”

September 2024: Trump says he ‘hates’ Taylor Swift

Well, we all know what happened next.

Posting on Truth Social on 15 September, Trump shared an all-caps post on Truth Social that read simply: “I HATE TAYLOR SWIFT.”

Taylor, meanwhile, is yet to publicly address the post from the Republican candidate.