Taylor Swift's relationship with Donald Trump started years before her May 2020 tweet against him. Digging into the archive of Trump's tweets shows that the former president used to like the pop star. On August 1, 2012, Trump tweeted thanking her for a picture, adding that she was "fantastic." Two months later, he applauded her latest achievement, writing, "Glad to hear that @taylorswift13 will be co-hosting the Grammy nominations special on 12.5. Taylor is terrific!"

Swift's first public diss at Trump came in 2018 when she posted on Instagram urging Tennessee citizens against voting for Marsha Blackburn. Blackburn was a U.S. Senate aspirant from the Republican party whom Trump endorsed. When the then-president heard of Swift's stance, he responded that he'd lost 25% of his interest in her music.

Trump clearly felt that Swift did something bad, but she did it again in May 2020 and once more three months later. The popstar called him out on X for his "calculated dismantling of USPS." She tweeted that Trump was "WELL AWARE that we do not want him as our president. He's chosen to blatantly cheat and put millions of Americans' lives at risk in an effort to hold on to power."