PoliticsKaroline Leavitt Calls 'Hilarious' Donald Trump 'the Best Boss' After Her Resignation: 'He's Nothing But Kind and Uplifting'
Former Press Secretary Karoline Leavitt gushed about her 'hilarious' ex-boss.
Oct. 16 2026, Published 12:20 p.m. ET
Former White House Press Secretary Karoline Leavitt praised President Donald Trump during an Instagram Q&A with followers on Wednesday, October 14.
When a fan asked whether Trump was nice or kind, Leavitt, 29, directly countered public perceptions, saying, "He's the best boss.”
She elaborated on her experience with the president, saying that while the public rarely sees this side of him, he has been "nothing but kind and uplifting to me, even since departing.”
The mom-of-two also called him "hilarious.”
Why Did Karoline Leavitt Step Down?
Karoline Leavitt said Donald Trump was 'the best boss.'
The social media banter touched on several other aspects of her time in administration and her recent life changes.
Leavitt reiterated that she stepped down as press secretary in late August to focus on motherhood and spend time with her two young children, shutting down online rumors about her exit.
Leavitt acknowledged the grueling nature of her former role, noting that she worked over 60 hours a week and had to remain on call around the clock.
Her high praise for Trump despite this demanding schedule drew mixed reactions and criticism on social media.
Despite Trump publicly undermining Leavitt, the former press secretary called him 'kind' and 'uplifting.'
Some users jokingly compared the Q&A to a Saturday Night Live skit, mocking the idea of calling someone the "best boss" immediately after detailing how they had to work over 60 hours a week and remain on call 24/7.
Detractors quickly resurfaced instances from earlier in her tenure where Trump publicly undermined her.
- Karoline Leavitt Gushes Over 'Generous' Donald Trump as She Praises President's 'Huge Heart': 'He's the Best Boss I Have Ever Had’
- Deflecting? Karoline Leavitt Blames Joe Biden for Causing His Press Secretary's 'Hard Time' in White House After Donald Trump's 'Poor Job' Dig
- Why Is Karoline Leavitt Leaving the White House? Everything to Know About Her Exit
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Social media found Leavitt's description of Trump as 'kind' quite ironic.
Critics pointed out the irony of calling him "kind" by sharing videos from April 2026, when Trump openly complained about negative press and told reporters in front of Leavitt that "maybe Karoline's doing a poor job" or a "terrible job.”
Commentators noted that her characterization glossed over what they described as a toxic work environment, arguing that Trump has a documented history of blaming his communication team for public relations issues he creates himself.
Detractors accused her of attempting to sanitize her intense, high-stakes political image into a softer media personality ahead of her upcoming contributor role at Fox News.
Who Took Over Karoline Leavitt's Position?
While Leavitt faced criticism for spewing propaganda, her replacement makes her absence felt deeply, even by her biggest critics.
While Leavitt has faced her share of heavy criticism, her August departure left a vacuum that new press secretary Katie Zacharia struggled to fill in her short, 14-minute debut briefing on Tuesday, October 13.
Former Biden White House Press Secretary Jen Psaki explicitly said she missed Leavitt on her MS NOW show after Zacharia’s disastrous debut briefing.
Opening her show on October 13, Psaki stated: "I am just going to start tonight by saying something that I never thought I would ever say. Karoline Leavitt, wherever you are out there, I miss you.”
