The Shady Side Of Karoline Leavitt

During his second term in the White House, President Donald Trump appointed Karoline Leavitt as the youngest press secretary in White House history. Leavitt's transformation through the years is admirable, and there's no doubt that she worked hard for the job. She recorded stellar grades throughout college, put up a spirited fight during her 2022 congressional run, and hasn't wavered in her public support for Trump.

In an interview with The Daily Signal, Leavitt raved about Trump's passion for the youth. "First of all, the president loves young people, and he wants to see young people succeed," Leavitt said. "I think that's part of the reason I have the honor of serving as his press secretary and he gave me this job. He's spoken publicly about it — how many people told him that I was too young to have this position — and he told me, 'You're not.'"

Since she stepped into the spotlight, Leavitt has made headlines for several reasons, including her hefty payday as Trump's press secretary and her worst press briefing outfits. While Leavitt's rise to the top of the political food chain is picture-perfect and inspiring, she has also raised eyebrows with questionable aspects of her character. From clashes with reporters, to presenting false information as facts, to lack of transparency with her campaign funds, here's the shady side of Leavitt.

In April 2025, The New York Times alleged that Karoline Leavitt's office discriminated against reporters who used pronouns to sign off their emails. The publication claimed that when one of its reporters emailed Leavitt to ask about the looming closure of a climate research facility, the press secretary wrote back: "As a matter of policy, we do not respond to reporters with pronouns in their bios." According to the outlet, another New York Times reporter experienced similar treatment while communicating with the Department of Government Efficiency (DOGE).

This presentation of pronouns has become synonymous with the LGBTQIA+ community, and President Donald Trump had earlier issued several directives that showed his administration's stance on gender identity. In January 2025, Trump signed an executive order that affirmed the recognition of two sexes — male and female. That same month, Trump enacted another executive order that barred gender-affirming treatment for people under the age of 19. He further cut federal funding toward transgender healthcare.

In February 2025, Trump banned transgender women and girls from taking part in women's sports. Speaking to the press, the president directed schools receiving federal funding to comply with the order or "be investigated for violations of Title IX," per NBC News. "With this executive order, the war on women's sports is over," Trump declared.

Karoline Leavitt has had several briefings since she took over the podium as White House press secretary, but not all the information she presents to the media is properly fact-checked. In her debut press briefing, Leavitt justified a freeze on USAID funding by claiming that "DOGE and OMB also found that there was about to be 50 million taxpayer dollars that went out the door to fund condoms in Gaza."

A fact-check afterward showed that USAID had only spent $46,000 on one donation of contraceptive pills and injectables in the Middle East within the first three years of Joe Biden's presidency, which was made to Jordan in 2023. Globally, the organization only spent $8.2 million on the distribution of male and female condoms in 2023, and none were delivered to the Middle East. In fact, USAID's total expenditure on condoms was not close to the $50 million mark. "It's a lie, they are making s*** up," an insider who formerly worked with the Biden administration told CNN.

In a similar manner, when the Trump administration deported Kilmar Abrego Garcia in March 2025, Leavitt said of the El Salvador native (via The New York Post), "Abrego Garcia was a foreign terrorist. He is an MS-13 gang member. He was engaged in human trafficking." Contrary to Leavitt's claims, U.S. courts determined that Garcia's deportation was wrongful, and allegations that he engaged in trafficking seemingly referenced a past brush with the police over speeding, during which no formal complaints were made.

Karoline Leavitt is no stranger to heated interactions with reporters, some of whom join the long list of people who can't stand her. In March 2025, Leavitt had an intense exchange with a journalist who raised concerns about the Trump administration's deportation criteria. The reporter argued that some tattoo symbols and clothes were faslely considered membership markers of the gang, Tren de Aragua, while an obviously irate Leavitt disagreed. Needless to say, Leavitt has not always kept her cool during charged moments.

In a June 2024 interview with CNN, Leavitt, who was the spokesperson for Donald Trump's campaign at the time, took a dig at the network and its anchors ahead of an upcoming debate against former president Joe Biden. "President Trump knows what he wants to say, and he's going to relay his vision to the American people to make this country strong, safe, secure and wealthy again," Leavitt told the host, Kasie Hunt (via People). "And that's why President Trump is knowingly going into a hostile environment on this very network, on CNN, with debate moderators who have made their opinions about him very well known over the past eight years and their biased coverage of him." When the press secretary brought up CNN host and moderator Jake Tapper, the spat resulted in Leavitt being cut short mid-interview.

Similarly, in February 2025, a couple of enthusiastic journalists were set to interview national security adviser Michael Waltz and special envoy to the Middle East Steve Witkoff. Amid the commotion on White House grounds, Leavitt told the reporters (via The National Desk), "Guys, let's act like adults here. They are generously offering their time to answer your questions. You don't need to scream at them like a bunch of school children."

Karoline Leavitt ran for a New Hampshire congressional seat in 2022. The then-25-year-old lost to Democratic candidate and incumbent congressman Chris Pappas, who was re-elected for a third term. Earlier, as the elections fast approached, an organization dubbed End Citizens United lodged a complaint with the Federal Electoral Commission (FEC) about Leavitt's campaign funding.

According to End Citizens United, Leavitt allegedly received $24,847 in excessive funding from individuals between July 19, 2021, and August 24, 2022. Leavitt also reportedly raised an additional $129,000 in surplus funds — over the legal contribution limit — after winning the Republican primary. The organization's president, Tiffany Muller, said of Leavitt, "Karoline Leavitt continues to prove she'll do whatever it takes to win this race, even if it means breaking the law. Under no circumstance is it plausible for Leavitt to claim that $150,000 in illegal contributions is a clerical error or a simple oversight. This was a calculated move to head into the final months of the election with more money. It's corruption plain and simple."

In February 2025, it emerged that Leavitt reportedly owed up to $325,000 to her campaign donors in unreturned refunds. She had reportedly kept the actual figures hidden during her initial filings with the FEC, ultimately sparking a debate about flaws in her political and campaign ethics.

Karoline Leavitt was a diehard MAGA supporter during Donald Trump's 2020 re-election bid, and when he lost the presidential election to Joe Biden, she spread his message: He was the winner. Leavitt later told WMUR-TV after she revealed her intention to run for Congress: "I believe, as millions of Americans across the country do, that there were irregularities and chaos across the country in the 2020 election due to the reforms that were made under the guise of pandemic precautions."

In her chat with the outlet, Leavitt acknowledged that Biden was indeed the president of the United States, but claimed that he had "destroyed our country through an economic crisis, a border crisis, a national security crisis and an energy crisis." As such, she presented her candidacy as an extension of Trump's agenda of putting America first.

While Leavitt spread the message of Trump's supposed win publicly, it was said that she didn't not believe in his victory behind closed doors. Two insiders revealed to The Washington Post that Leavitt had told them in confidence that Biden won fairly. However, when the press secretary was questioned by the publication, she claimed not to remember having such discussions.

In February 2025, the Associated Press alleged that one of its reporters was restricted from White House Oval Office coverage following the publication's reference of the Gulf of Mexico by its original name, as opposed to the Trump-rebranded "Gulf of America." When CNN reporter Kaitlan Collins made an inquiry about the incident during a press briefing, Karoline Leavitt answered (via LiveNOW from Fox), "Let me just set the record straight. It is a privilege to cover this White House ... Nobody has the right to go into the Oval Office and ask the president of the United States questions. That's an invitation that is given."

The Associated Press decided to take Leavitt and her colleagues, White House chief of staff Susan Wiles and her deputy, Taylor Budowich, to court. In its filing, the publication accused the White House of interfering with the media's right to free speech. "The press and all people in the United States have the right to choose their own words and not be retaliated against by the government," AP remarked, and Leavitt responded with a few words: "We'll see them in court."

In April 2025, U.S. District Judge Trevor N. McFadden ruled that the White House was in the wrong and ordered the return of the Associated Press back into the Oval. However, the publication's journalists were still barred from presidential coverage during Trump's appearance at the National Republican Congressional Committee dinner.

Karoline Leavitt wasn't expecting to be celebrated by White House reporters when she became the press secretary. On "My View with Lara Trump," Leavitt said of her first press briefing, "It definitely was a moment seeing just a sea of people who want to make me look bad."

It didn't take long before Leavitt developed a feud with CNN reporter Kaitlan Collins. The duo was off to a rough start during Leavitt's debut as press secretary, since Collins had a string of questions about Donald Trump's decision to freeze foreign aid and his Department of Justice purge. It's clear that Leavitt can't stand Collins because the reporter has previously butted heads with her boss, president Trump.

In March 2025, Collins and Leavitt went back and forth as the former referenced a post on Truth Social in which president Trump alleged that pardons issued by former president Joe Biden were "declared VOID, VACANT, AND OF NO FURTHER FORCE OR EFFECT, because of the fact that they were done by Autopen." Leavitt expressed doubt that Biden was cognizant of the fact that his signature was being used on pardons, and when Collins asked if there was evidence to back up her claim, Leavitt quipped (via Fox 26 Houston), "You're a reporter. You should find out." In a similar manner, when Collins requested to ask a follow-up question on Yemen attack plans leaking (details on this next) during another press briefing, Leavitt blatantly told the reporter (via The National Desk), "Kaitlan, I'm not taking your follow-up."

In March 2025, The Atlantic's editor in chief, Jeffrey Goldberg, alleged that he was accidentally added to a Signal group chat with key national security personnel, following an invite from national security adviser Michael Waltz. Goldberg claimed that he was subsequently made aware of plans of attacks on Yemen. "The world found out shortly before 2 p.m. eastern time on March 15 that the United States was bombing Houthi targets across Yemen," Goldberg wrote in The Atlantic. "I, however, knew two hours before the first bombs exploded that the attack might be coming. The reason I knew this is that Pete Hegseth, the secretary of defense, had texted me the war plan at 11:44 a.m. The plan included precise information about weapons packages, targets, and timing."

Goldberg further alleged that most members of the group celebrated after the success of the strikes, which had resulted in a death toll of 53 at the time of writing. In response to the journalist, Karoline Leavitt shared a screenshot of the article on X and accused him of fabricating the story. "This entire story was another hoax written by a Trump-hater who is well-known for his sensationalist spin," Leavitt wrote.

Pete Hegseth himself also dismissed Goldberg's claims, but it was later reported that he had shared attack plans with members of his family, including his wife, brother, and attorney. In a conversation with "Fox & Friends," Hegseth confirmed that there was a leak, saying, "What was shared over Signal then and now, however you characterize it, was informal, unclassified coordinations for media coordination and other things."

Karoline Leavitt had a preferred candidate during the 2024 presidential run, and it clearly wasn't former Vice President Kamala Harris. Leavitt acted in her capacity as Trump's media spokesperson and took every opportunity to criticize the Democratic candidate. Harris was first announced as former President Joe Biden's replacement in the presidential race in August 2024, and she had her first sit-down interview on CNN alongside her running mate, Tim Walz, later that month.

Following the interview, Leavitt took to "Jesse Watters Primetime" to take jabs at Harris: "Well, I think it's pitiful that the Democrat nominee for president of the United States dodges the press for 40 days, goes into a safe space for her first big sit-down interview, can't do it alone — has to bring her male running mate with her, by the way — when she's trying to be the first woman president of the United States. What message does that send to young women and girls across this great country?"

Similarly, in a September 2024 conversation with "Newsmax," Leavitt responded to world leaders like Vladimir Putin and Volodymyr Zelensky's interest in a Harris presidency by saying, "They know, and the world knows, that Kamala Harris will continue to throw the United States under the bus to appease our adversaries to continue this globalist mindset that we have had over the past four years."

Karoline Leavitt has long expressed her disdain for traditional media and its values. As a communication and political science student at Saint Anselm College, Leavitt wrote an article for The Saint Anselm Crier, in which she called out mainstream media — especially left-leaning networks — for sidelining Donald Trump ahead of the 2016 presidential elections. "Liberals themselves will never admit it, but any rational and open minded individual can see the ever present bias that engulfs the media day in and day out," Leavitt wrote, adding, "Major news stations such as CNN, ABC and MSNBC might as well come out and endorse Hillary Clinton."

Even as White House press secretary, her preference towards non-traditional media has shown through. In April 2025, Leavitt hosted the first-ever "influencer briefing," welcoming online social media personalities into the White House. "As I promised in my first briefing as press secretary back in January, the Trump White House will speak to all media outlets and personalities, not just the legacy media who traditionally has covered this institution," she proclaimed.

Although Leavitt has been a strong media critic, she ironically tried to pursue a career in journalism. She applied for an internship at Fox News and even founded a broadcasting club at Saint Anselm College. In fact, Leavitt's first brush with politics was at a media event, as she told Politico: "As a student during the 2016 election, I was granted the opportunity to work for Fox News and meet several presidential candidates on my campus during the week of the New Hampshire primary. That experience was my first glimpse into the world of press, and I knew I wanted to pursue it in my career post-grad."