Trump Pits ‘Woke’ Taylor Swift Against Sydney Sweeney, Saying Pop Star Is for ‘Losers’ and Calling Sweeney’s Ad the ‘Hottest’

Donald Trump is pitting Sydney Sweeney and Taylor Swift against each other by casting them as opposing sides of the celebrity coin.

When Trump discovered that Sweeney is a registered Republican while speaking with reporters on Sunday, Aug. 3, he praised the actress and her controversial American Eagle campaign, which has come under fire for its perceived problematic undertones.

In a Truth Social post on Monday morning, the president took his newfound affection for Sweeney a step further by contrasting his appreciation for the actress with his “hate” for Swift, who backed Democrat Kamala Harris in the 2024 presidential election.

“Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there. It’s for American Eagle, and the jeans are ‘flying off the shelves.’ Go get ‘em Sydney!” he wrote on Aug. 4.

After slamming ads from other companies like Bud Lite and Jaguar — which Trump described as “woke” — the president then shifted the conversation to Swift, who has become a frequent target of his anger over the past year.

“Just look at Woke singer Taylor Swift,” he wrote in the post. “Ever since I alerted the world as to what she was by saying on TRUTH that I can’t stand her (HATE!). She was booed out of the Super Bowl and became, NO LONGER HOT.”

He continued: “The tide has seriously turned — Being WOKE is for losers, being Republican is what you want to be. Thank you for your attention to this matter!”

The president’s modern criticism of Swift escalated after she endorsed Harris for president in September 2024. The endorsement prompted Trump to post: “I HATE TAYLOR SWIFT!”

Despite Trump’s attempts to turn his MAGA followers against Swift, the president’s granddaughter Arabella remained a fan of the “Blank Space” singer, even celebrating her 13th birthday with mom Ivanka at the Eras Tour in October.

Sweeney’s party preference was first reported by Buzzfeed News amid the backlash from her controversial new partnership with American Eagle, though the actress has not commented on her political affiliation or spoken publicly in support of Trump.

The AE ad campaign — called “Sydney Sweeney Has Great Jeans” — played off the word “genes,” with critics claiming that it suggested she was genetically superior in the way that it highlighted her blonde hair and blue eyes.

The jeans campaign also drew comparisons to Brooke Shields‘ controversial Calvin Klein ad from 1980. Shields’ age (she was 15 at the time) ruffled feathers due to the commercial’s provocative tagline: “You want to know what comes between me and my Calvins? Nothing.” It also featured similar messaging about passing down characteristics from generation to generation.

Donald Trump is pitting Sydney Sweeney and Taylor Swift against each other by casting them as opposing sides of the celebrity coin.

When Trump discovered that Sweeney is a registered Republican while speaking with reporters on Sunday, Aug. 3, he praised the actress and her controversial American Eagle campaign, which has come under fire for its perceived problematic undertones.

In a Truth Social post on Monday morning, the president took his newfound affection for Sweeney a step further by contrasting his appreciation for the actress with his “hate” for Swift, who backed Democrat Kamala Harris in the 2024 presidential election.

“Sydney Sweeney, a registered Republican, has the ‘HOTTEST’ ad out there. It’s for American Eagle, and the jeans are ‘flying off the shelves.’ Go get ‘em Sydney!” he wrote on Aug. 4.

After slamming ads from other companies like Bud Lite and Jaguar — which Trump described as “woke” — the president then shifted the conversation to Swift, who has become a frequent target of his anger over the past year.

“Just look at Woke singer Taylor Swift,” he wrote in the post. “Ever since I alerted the world as to what she was by saying on TRUTH that I can’t stand her (HATE!). She was booed out of the Super Bowl and became, NO LONGER HOT.”

He continued: “The tide has seriously turned — Being WOKE is for losers, being Republican is what you want to be. Thank you for your attention to this matter!”

The president’s modern criticism of Swift escalated after she endorsed Harris for president in September 2024. The endorsement prompted Trump to post: “I HATE TAYLOR SWIFT!”

Despite Trump’s attempts to turn his MAGA followers against Swift, the president’s granddaughter Arabella remained a fan of the “Blank Space” singer, even celebrating her 13th birthday with mom Ivanka at the Eras Tour in October.

Sweeney’s party preference was first reported by Buzzfeed News amid the backlash from her controversial new partnership with American Eagle, though the actress has not commented on her political affiliation or spoken publicly in support of Trump.

The AE ad campaign — called “Sydney Sweeney Has Great Jeans” — played off the word “genes,” with critics claiming that it suggested she was genetically superior in the way that it highlighted her blonde hair and blue eyes.

The jeans campaign also drew comparisons to Brooke Shields‘ controversial Calvin Klein ad from 1980. Shields’ age (she was 15 at the time) ruffled feathers due to the commercial’s provocative tagline: “You want to know what comes between me and my Calvins? Nothing.” It also featured similar messaging about passing down characteristics from generation to generation.