Fox News liberal rotating co-host Jessica Tarlov, who appears on “The Five,” says President Donald Trump sent her a customized “Trump 2028” hat as a Christmas gift — and she wants no part of it. Appearing this week on the MeidasTouch program “On Sunday with Jack Cocchiarella,” Tarlov made clear she has no intention of warming up to the president, regardless of the gesture.
A Gift She Did Not Want
The 42-year-old Democratic political strategist joined Fox News as a contributor in 2017 and has since become one of the network’s most recognizable liberal voices. She revealed the holiday detail while promoting her upcoming book, “I Disagree: Winning Arguments Without Losing Friends.” Her forthcoming book focuses on persuasive communication that preserves relationships — an approach Tarlov appears to be applying selectively when it comes to the White House.
Trump, 80, has been selling “Trump 2028” hats since April 2025, even as the Constitution explicitly bars him from seeking a third term. He previously acknowledged the document is “pretty clear” that he is “not allowed” to run again. Nevertheless, Trump has continued to tease another campaign — most recently stating his plan to pursue what he called a fourth presidential term. He also displayed a “Trump 2028” hat during the July 24, 2026, White House Correspondents’ Association Dinner.
Tarlov was not amused by her personalized piece of that merchandise. She told the program that Trump included a note thanking her for her support, acknowledging it was meant as a joke. Tarlov said she believes Trump “will do everything in his power to be able to stick around as long as possible — and certainly if Steve Bannon gets his way,” adding that she is “not really interested in palling around or playing nice.”
Bannon’s Prediction and a Constitutional Warning
Tarlov’s reference to former Trump White House chief strategist Steve Bannon, now a MAGA podcaster, was pointed. Bannon has publicly predicted that Trump will run in 2028 and win, despite the Constitution’s prohibition on a third term. Tarlov appears to take that possibility seriously — not as a legal reality, but as a signal of intent that she finds worth tracking rather than dismissing as political theater.
Some of Tarlov’s colleagues at Fox News have encouraged her to meet the president in person, telling her she would come away charmed. She pushed back on that idea directly. Tarlov said she has no interest in being charmed by Trump and believes it’s safer to maintain her distance. She also noted, with characteristic candor, that she is “not good at faking a smile.”
Tarlov Draws a Line — but Defends Mamdani
Tarlov’s reluctance to engage with Trump personally does not mean she believes every Democrat should keep their distance. She offered a nuanced defense of New York City Mayor Zohran Mamdani, who met with Trump at the White House on November 21 last year. Rather than condemning the meeting, Tarlov argued Mamdani handled it correctly — securing what she described as billions of dollars in investment for New York without softening his criticism of the president or compromising his stated values. She noted that Mamdani was not even smiling in photos from the encounter, suggesting he treated it as a business transaction rather than an endorsement.
The distinction Tarlov drew was clear: a photo op with tangible results for constituents is defensible; charming a president for its own sake is not — at least not for her.
Trump’s Past Attacks on Tarlov
The dynamic between Tarlov and Trump has not always been one of playful Christmas gifts. In April, Trump criticized Tarlov on Truth Social after she reported his negative poll numbers on “The Five,” calling her “one of the Least Attractive and Talented People on all of Television” and claiming her voice was “so grating and terrible” he had to turn her off. He also demanded that Fox News executives pull her from the air entirely, branding her “a real loser.” Fox News did not remove her. Tarlov had noted at the time that Trump held a 35 percent approval rating in most polls — the kind of data point that prompted the attack.
Tarlov continues as a rotating co-host on “The Five,” where she is frequently the sole liberal voice at the table pushing back on pro-Trump commentary. Her book, “I Disagree: Winning Arguments Without Losing Friends,” is framed around exactly that skill set — making the case for a position without sacrificing the relationship. When it comes to Trump himself, however, she seems to have decided the friendship was never on the table to begin with.
