Politics

Trump’s Unexpected Well Wishes: How the Political Landscape Shifts with Taylor Swift’s Engagement

Trump wished Swift & Kelce luck after their engagement, despite past criticisms and political differences.

byEditorial Staff

August 27, 2025, 11:14 AM

Taylor Swift in a sweater and sunglasses, walking with a red and white polka dot scarf

Taylor Swift in Hyannisport, Massachusetts, on July 30, 2012. By Shutterstock.com / Robert Scott Button.

Executive Summary

President Donald Trump offered well wishes to Taylor Swift and Travis Kelce on their engagement, marking a shift in his public commentary on the singer.

Trump’s current positive remarks stand in stark contrast to his past criticisms and attacks on Swift.

Taylor Swift has been an outspoken critic of Trump and has publicly endorsed his political opponents.

The Story So Far

Donald Trump’s recent positive remarks regarding Taylor Swift and Travis Kelce’s engagement represent a notable shift, as Trump has a documented history of publicly criticizing Swift, including personal attacks and questioning her political affiliations. This change in tone is particularly significant given that Swift has been an outspoken critic of Donald Trump and has actively endorsed his political opponents, setting a backdrop of political animosity for this unexpected well-wishing.

Why This Matters

Donald Trump’s shift from criticizing Taylor Swift to offering well wishes for her engagement, despite her vocal opposition and endorsement of his political rivals, signals a potential strategic attempt to soften his image or appeal to a broader demographic, acknowledging the immense cultural and political influence of figures like Swift, particularly as the 2024 election approaches.

Who Thinks What?

Donald Trump offered well wishes to Taylor Swift and Travis Kelce on their engagement, calling them “terrific” and “great” people.

Donald Trump previously criticized Taylor Swift, stating he “hates” her, questioned her political leanings, and attacked her appearance.

Taylor Swift is an outspoken critic of Donald Trump, accusing him of “gaslighting the American public,” and has publicly endorsed his political opponents.

President Donald Trump offered well wishes to superstar Taylor Swift and Kansas City Chiefs tight end Travis Kelce following their engagement announcement on Tuesday, marking a notable shift in his public commentary on the singer. The former president’s remarks come after a history of public criticism towards Swift, who has also been a vocal critic of Trump and has endorsed his political opponents.

Trump’s Shifting Tone

Speaking on the engagement, Trump stated, “Well, I wish them a lot of luck.” He added, “I think he’s a great player, I think he’s a great guy and I think that she’s a terrific person. So I wish them a lot of luck.”

Swift announced her engagement to her 280 million Instagram followers earlier Tuesday. She shared snapshots of herself and Kelce embracing in a flower-filled garden, showcasing what appeared to be an engagement ring.

Past Criticisms and Political Stances

Trump’s recent comments stand in stark contrast to his previous statements regarding Swift. In May, he reportedly attacked Swift on Truth Social, saying he “hates” her and that she was “no longer HOT.”

In February, Trump claimed Swift was “booed out of the stadium” at the Super Bowl, where Kelce’s Kansas City Chiefs lost to the Philadelphia Eagles. Trump attended that Super Bowl, picking the Chiefs to win beforehand and praising quarterback Patrick Mahomes and his wife, Brittany, whom he identified as a “Trump fan.”

Last summer, Trump had also commented on Swift’s appearance, calling her “very beautiful,” but questioned her political leanings. He pondered whether the entertainer was “legitimately liberal” or if it was “just an act.”

Swift has been an outspoken critic of Donald Trump, stating in 2019 that he was “gaslighting the American public.” She has also publicly endorsed former Vice President Kamala Harris’s 2024 White House bid, further cementing her opposition to Trump’s political agenda.

The former president’s change in tone regarding one of the world’s most influential cultural figures, especially one who has politically opposed him, highlights the complex interplay between celebrity influence and political discourse.