Jessica Tarlov, the Democratic political strategist who serves as a rotating liberal co-host on Fox News’ “The Five,” disclosed in an interview that she received an unwanted Christmas present from President Donald Trump: a personalized “Trump 2028” cap. During her late July appearance on the MeidasTouch show “On Sunday with Jack Cocchiarella,” the 42-year-old made her position unmistakable.
Constitutional Concerns Behind the Merchandise
The president, who is 80, has been selling the caps since April 2025, despite the Constitution’s clear prohibition on seeking a third term. Trump himself has acknowledged the document is “pretty clear” that he is “not allowed” to run again. Still, he has repeatedly floated the idea of another campaign, recently describing his intention to pursue what he termed a fourth presidential term. On July 24, 2026, during the White House Correspondents’ Association Dinner, he wore one of the hats.
Tarlov joined Fox News in 2017 as a contributor and has emerged as one of the network’s most prominent liberal commentators. She was promoting her new book during the interview, “I Disagree: Winning Arguments Without Losing Friends,” which centers on maintaining relationships while engaging in persuasive debate—a principle she is apparently not extending to the current administration.
Trump’s Past Attacks on Tarlov
The relationship between Trump and Tarlov has been contentious. In April, after she discussed his unfavorable polling data on “The Five,” noting his 35 percent approval rating in most surveys, the president attacked her on Truth Social. He described her as “one of the Least Attractive and Talented People on all of Television,” complained her voice was “so grating and terrible” that he had to turn her off, and insisted Fox News executives remove her from the air, calling her “a real loser.” The network declined to do so.
The hat came with a note in which Trump thanked her for her support, which she recognized as a joke. But Tarlov told the program 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
Her mention of Steve Bannon, the former White House chief strategist turned MAGA podcaster, was deliberate. Bannon has publicly stated he expects Trump to run and win in 2028, notwithstanding the constitutional bar on a third term. Tarlov treats that forecast as worth monitoring—not because it represents a legal possibility, but because it reflects an ambition she views as worth watching rather than dismissing outright.
Colleagues at Fox News have urged her to meet Trump in person, suggesting she would find him charming. She rejected the suggestion outright, saying she has no desire to be charmed and considers it wiser to keep her distance. She also admitted she is “not good at faking a smile.”
Tarlov Draws a Line — but Defends Mamdani
Her refusal to engage Trump personally doesn’t extend to all Democrats. She defended New York City Mayor Zohran Mamdani, who traveled to the White House for a November 21, 2025 meeting with Trump. Tarlov praised Mamdani’s handling of the meeting, arguing he obtained what she called substantial financial commitments for New York while maintaining his critical stance toward the president and his principles. She pointed out that Mamdani wasn’t even smiling in photographs from the visit, treating it as a pragmatic transaction rather than an endorsement.
A Gift She Did Not Want
The difference Tarlov outlined was straightforward: meeting a president to deliver tangible benefits for voters is justified; becoming friendly with him for no clear purpose is not—at least not in her case. She remains on “The Five” as a rotating co-host, frequently serving as the lone liberal voice countering pro-Trump commentary. Her forthcoming book focuses precisely on that capacity—advancing an argument without destroying the relationship. When it comes to Trump, though, she appears to have concluded there was never a relationship to preserve.
