Jessica Tarlov, a Democratic political strategist who serves as a rotating co-host on Fox News’ “The Five,” disclosed that President Donald Trump mailed her a personalized “Trump 2028” hat for Christmas — and she has zero interest in the gesture. The 42-year-old made the revelation during a late July appearance on the MeidasTouch show “On Sunday with Jack Cocchiarella,” where she promoted her forthcoming book and made her stance toward the White House unmistakably clear.
Trump’s Third-Term Tease and Constitutional Limits
Since April 2025, the 80-year-old president has been selling merchandise emblazoned with “Trump 2028,” despite the fact that the Constitution explicitly prohibits a third term. Trump himself has acknowledged the document is “pretty clear” that he is “not allowed” to run again, yet he continues floating the idea — recently claiming he intends to pursue what he described as a fourth presidential term. He even wore one of the hats to the White House Correspondents’ Association Dinner on July 24, 2026.
Tarlov received her own custom version of that hat, complete with a handwritten note from Trump thanking her for her support — a joke, she acknowledged, but one she did not find funny. She 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.”
A History of Personal Attacks
The relationship between Trump and Tarlov has been contentious. In April, after Tarlov reported on “The Five” that the president held a 35 percent approval rating in most polls, Trump lashed out on Truth Social, branding her “one of the Least Attractive and Talented People on all of Television” and describing her voice as “so grating and terrible” that he had to turn her off. He went further, demanding Fox News executives remove her from the air and calling her “a real loser.” The network did not comply, and Tarlov remains in her role.
Tarlov became a Fox News contributor in 2017 and has subsequently emerged as one of the most prominent liberal voices on the network. Her upcoming book, “I Disagree: Winning Arguments Without Losing Friends,” centers on persuasive communication that maintains relationships — a philosophy she appears willing to apply everywhere except the Oval Office.
Colleagues Urge Her to Meet Trump; She Declines
Several of Tarlov’s Fox News colleagues have pushed her to meet Trump face-to-face, insisting she would find him charming. She rejected the suggestion outright, saying she has no desire to be won over by the president and considers it wiser to keep her distance. She also admitted, with typical directness, that she is “not good at faking a smile.”
Her mention of Steve Bannon, the former chief strategist in Trump’s White House who now hosts a MAGA podcast, was intentional. Bannon has publicly forecast that Trump will run in 2028 and win, Constitution be damned. Tarlov appears to view that prediction not as a legal possibility, but as a troubling indication of ambition she believes warrants vigilance rather than dismissal as mere political theater.
Defending Mamdani’s White House Visit
While Tarlov refuses personal engagement with Trump, she does not believe all Democrats should follow suit. She defended New York City Mayor Zohran Mamdani, whose White House meeting with Trump took place on November 21, 2025. Tarlov argued Mamdani approached the encounter correctly — extracting what she characterized as commitments worth billions of dollars for investment in New York while refusing to soften his criticism of the president or abandon his principles. She pointed out that Mamdani wasn’t even displaying a smile in photographs taken during the meeting, treating it as a transaction rather than an endorsement.
The line Tarlov drew was precise: a calculated meeting that delivers concrete benefits for constituents is justifiable; succumbing to presidential charm simply because it’s offered is unacceptable — at least from her perspective. She continues as a rotating co-host on “The Five,” often serving as the lone liberal voice countering pro-Trump commentary at the table. Her forthcoming book is built around precisely that skill — advancing an argument without destroying the relationship. When it comes to Trump, however, she seems convinced no relationship was ever on offer.