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In our 38th episode of This F*cking Guy, Erin and Alyssa dive deep into the past of the MAGA mouthpiece, Karoline Leavitt. From “growing up in a small business family” to her college broadcasting days, to being the ultimate tradwife hypocrite, to shapeshifting into an obsequious Trump a** kisser, this may be one of our most irritating guys yet!

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email transcripts@crooked.com and include the name of the podcast.

Saint Anselm Broadcasting Club (YouTube)

US Rep. Chris Pappas projected to defeat Republican challenger Karoline Leavitt to win third term (WMUR)

The question that ruffled Karoline Leavitt’s feathers (Granite Memo)

First Congressional District GOP Primary at NHIOP, 8/4/22 (YouTube)

‘It’s Those Lips’: Trump, 79, Goes Gaga for Karoline Leavitt, 27 (Daily Beast)

Karoline Leavitt Gives Jaw-Dropping Defense of Trump’s Racist Obama Video (Daily Beast)

Karoline Leavitt Says MAGA Shooter Just Hated Mormons (Daily Beast)

White House press secretary Karoline Leavitt previews State of the Union (NBC News)

Karoline Leavitt Admits Her Family Had a Hard Time Accepting 32-Year Age Gap with Husband Nicholas Riccio (People)

NH Primary Source: Leavitt says Dems ‘abandoned’ her family’s business despite COVID relief loans (WMUR)

It may be her first campaign, but building blocks of Leavitt’s politics were laid years ago (NHPR)

Meet the assistant press secretary (Eagle Tribune)

Gun Shoot Will Conclude Former Trump Aide’s House Primary Race (NY Times)

Highlight Her | Karoline Leavitt (YouTube)

Inside Project 2025’s Secret Training Videos (ProPublica)

Wonder Woman Karoline Leavitt: Her Life as a New Mom & Trump’s Spokeswoman (The Conservateur)

The question that ruffled Karoline Leavitt’s feathers (Granite Memo)

FACT FOCUS: No evidence that $50 million was designated by the US to buy condoms for Hamas (AP News)

The Political Education of Karoline Leavitt (Politico)

American media: distorting the truth for political objectives (The Saint Anselm Crier)

Trump press secretary pick removed post praising Pence on January 6, then ran for Congress as an election denier (CNN)

President Trump’s travel ban is for America’s own benefit (The Saint Anselm Crier)

Leavitt earns third PolitiFact check, exceeding career total of predecessor Jen Psaki (NBC News)

Karoline Leavitt is a professional liar (Stop The Presses)

Karoline for Congress | Fox & Friends 7/20/21 (YouTube)

All Illegal Immigrants Are Criminals, Says Trump’s Press Secretary Karoline Leavitt | Live (YouTube)

Karoline Leavitt says French should be ‘grateful’ to US they are ‘not speaking German’ (YouTube)

Karoline Leavitt, 28, Called Out for ‘Photoshopping’ Husband, 60 (Daily Beast)

Leavitt Rips Pope For Declining Board Of Peace Invite (Joe. My. God.)

“MAGA GOP view of Trump, approve is 100%. If you are a member of MAGA in the GOP, you approve of Donald John Trump. 0% say that they disapprove… he’s the 1972 Miami Dolphins.” (@PressSec)

 

TRANSCRIPT

 

Erin Ryan: Welcome to another episode of This F*cking Guy, the show where we spotlight one fucking guy making America worse and explain why they suck. I’m Erin Ryan, host of Crooked Media’s Hysteria podcast.

 

Alyssa Mastromonaco: And I’m Alyssa Mastromonaco, the other host of Crooked Media’s Hysteria Podcast.

 

Erin Ryan: Alyssa, have you ever seen the movie, Election?

 

Alyssa Mastromonaco: Oh yes, it’s a classic 1999 dark comedy starring Reese Witherspoon and Matthew Broderick about a high school teacher who’s dislike for a hard-driving, ambitious student causes him to get involved in sabotaging a student government election. Reese Witherspoon turns in a generationally iconic performance as the annoying try-hard Tracy Flick.

 

Erin Ryan: Well it occurred to me while I was researching this episode’s subject, that MAGA has its own Tracy Flick. It’s Karoline Leavitt.

 

Alyssa Mastromonaco: Yes maam.

 

Erin Ryan: Who went from failing to become the youngest member of Congress ever to succeeding in becoming the youngest White House press secretary ever.

 

Alyssa Mastromonaco: Wow, the parallels are uncanny, down to the way she holds her face.

 

Erin Ryan: I know, now you can’t unsee it. So let’s be fair to Tracy Flick here. Flick seems to at least have some original thoughts of her own. And all of Leavitt’s thoughts and opinions are copy pasted from the addled brain of Donald Trump. And have been since she was a teenager, as you’ll see.

 

Alyssa Mastromonaco: On one hand, you have to respect the hustle. Apparently, Leavitt has got the work ethic of a border collie on cocaine, but that sort of work ethic driven by ambition for ambition’s sake is a recipe for, at the very least, a deeply obnoxious person. At most, the political equivalent of the scary cop Terminator.

 

Erin Ryan: So let’s get into the life and times of the 28-year-old White House press secretary who is poised to be the youngest woman ever to throw her back out flaring her nostrils. Karoline Claire Leavitt was born on August 24th, 1997 in Atkinson, New Hampshire, to what she describes incessantly as a blue-collar middle-class family.

 

Alyssa Mastromonaco: That’s Karoline with a K. She’d fill in the other two Ks later in life.

 

Erin Ryan: And when I say she talks about how down-home and red-stayed she is, I mean she talks it constantly. Since before her frontal lobe was even done developing, she’s been on a Justin Timberlake style world tour, promoting herself as Miss Middle Class U.S.A.

 

Alyssa Mastromonaco: For as often as she tells her own story, you’d think she’d be able to get it straight, but there are some weird variations in how she talks about herself depending on who she’s talking to.

 

[clip of Karoline Leavitt]: Yeah, I grew up in New Hampshire in a quintessential New England town of 2000 people. I grew in a middle-class, blue collar family, small business owners. My family owns businesses here. Business family. Small business family. Grew up here in a business family I grew a business business family, like my family is not political at all. I was raised in a family that was not political at all, middle-class, working class people.

 

Alyssa Mastromonaco: Business family, working class. She’s salt to the earth. Just to clarify, according to basically every profile written about Karoline Leavitt, her dad didn’t own a trucking business as much as he owned a used car dealership.

 

Erin Ryan: Right. Trucking business sounds so much more red state though. Her family also owned an ice cream shop where Karoline worked during the summers. Leavitt’s two older brothers were athletes. Karoline was an athlete as well, playing multiple sports, but really excelling at softball.

 

Alyssa Mastromonaco: Fucking knew it was gonna be softball!

 

Erin Ryan: You know what? What press secretary doesn’t love softballs? [laughter] She was good enough at the old underhanded heave-ho that she earned an athletic scholarship to play D2 college softball at St. Anselm’s College, a Catholic school in Manchester, New Hampshire.

 

Alyssa Mastromonaco: She was OK at softball in college, OK, but not great. She started in 36 games her freshman year and was even named conference freshman of the week once. But after that her softball career kind of fizzled out and her heart wasn’t in it.

 

Erin Ryan: Her heart was in a grieved whining about how mean people are to conservatives on college campuses. Like many college conservatives, she found her perfect outlet for her complaints in her school paper, where she proved to be a pretty shitty writer. But don’t take my word for it, this is from an August 31, 2016, Leavitt byline, quote, “The liberal media—It is debatably the most appalling factor of the entire election cycle, besides Hillary Clinton somehow dodging an indictment, of course. 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. Major news stations such as CNN, ABC, and MSNBC might as well come out and endorse Hillary Clinton.”.

 

Alyssa Mastromonaco: Wow, a budding Susan Sontag.

 

Erin Ryan: She also wrote a column claiming that Donald Trump’s Muslim ban wasn’t actually a Muslim ban. So she’s been a whiny and kind of dumb sounding Trump copy-paster since before she was old enough to buy lottery tickets. And this should be a lesson for all kids with dreams out there. If you’re really good at sounding stupid, follow your stupidity to the dumbass stars.

 

Alyssa Mastromonaco: According to a Politico profile, Leavitt’s first national TV appearance happened in 2015 when she went on a Pancakes in Politics town hall hosted by Matt Lauer. This is pre-Me Too Matt Laur when he was still flying high hosting the Today Show.

 

Erin Ryan: On that fateful day, baby Karoline, just 18 at the time, was given the opportunity to ask then candidate Donald Trump a question. Her question was, quote, “Mr. Trump, as everybody knows and I personally appreciate, what would like to say to people who think you are too harsh to be the next president?”.

 

Alyssa Mastromonaco: She’s been kissing that man’s ass for so long that her lips and his butt are common-law married.

 

Erin Ryan: Yep, and we know Trump loves being flattered, so of course he complimented the question and claimed to be a nice guy before launching into a complaint about how people running the country are stupid. By the end of her sophomore year, Leavitt had grown frustrated with the slow publishing turnaround of the campus newspaper and turned her sights on her true passion, being on television. She started the St. Anselm Broadcast Club, a group for other aspiring Matt Lauers. Leavitt scored a job with a local TV station and covered the 2016 election too. Thanks to her college’s place in America’s archaic primary system, she even got the opportunity to rub elbows with such bastions of truth as Tucker Carlson. And that creepy one who reminds me of a pig with a nose job?

 

Alyssa Mastromonaco: Brett Baier.

 

Erin Ryan: Brett Baier. Yes. After the rush of Donald Trump winning the presidency had subsided, Karoline’s Kids Club put together its own YouTube channel and racked up tens of views. For those listening, instead of watching, I need to describe the quality of these videos. Just like most college clubs, the broadcast club couldn’t afford its own fancy studio. So instead of trying to make do with what they had, they green-screened each commentator into a higher-res photo of a fancy TV studio, giving the whole thing a low-budget Tim and Eric vibe. Spaghett—

 

[clip of Karoline Leavitt]: Last Friday, Donald J. Trump swore into the highest office in the land, becoming the 45th president of the United States of America. Joining me to discuss Trump’s changes so far is Hillary Clinton supporter and our very own political analyst, Tom Mannion. As an avid Clinton supporter, and Democrat, how did you feel last Friday watching Trump swear in to the Oval Office.

 

[clip of Tom Mannion]: You know, it was very symbolic, and even as a Democrat, I love to see the peaceful transfer of power. It doesn’t happen in a lot of countries, and to see it go from President Obama to President Trump was very touching.

 

[clip of Karoline Leavitt]: And I mean, everyone can expect the peaceful transfer of power in this country. That’s what makes America so great.

 

Erin Ryan: Yeah. Wow. So you admit, so you admit it? You like the peaceful transfer of power?

 

Alyssa Mastromonaco: She got better at sitting behind a desk and talking in the direction of a camera as time went on, like when she experimented with pretending to type before looking up at the camera as though startled. [laughter] Anyway, this is why people practice to get better.

 

Erin Ryan: Leavitt applied for an internship working for the Trump White House, something she’s recounted in interviews with awe as something she literally applied for online. As though filling out a job application on the internet is a splendid novelty like the chocolate river in Willy Wonka’s factory. While Karoline ended up getting her golden ticket from the man with the golden toilet and won an internship to work for the Trump white house the summer before her senior year. At the time, White House internships were generally unpaid, which is incongruous with Leavitt’s allegedly middle-class upbringing.

 

Alyssa Mastromonaco: Yeah, where would she get the money to survive in DC if her parents were such business bumpkins or whatever?

 

Erin Ryan: Right, like, plenty of small business owners are successful enough to bankroll their kids’ unpaid internships into their 20s. Like, how do you think we staff art museums? But this red state poverty legend building is something that upper middle class people do all the time to boost their blue collar bona fides. Karoline’s dad ran a used car dealership. Car dealerships are the number one producer of millionaires in the American economy. Given the unpaid internship of it all, I’m highly suspicious that Leavitt’s claims of being middle-class are exaggerated. And to me, someone who grew up legit without money, that is a form of stolen valor.

 

Alyssa Mastromonaco: Fair enough. Karoline’s first job was in the correspondence office, which means she read random letters and cards that people sent to the White House and responded to some of them.

 

Erin Ryan: Leavitt was offered a job as assistant press secretary after graduating the following year, working mostly under Kayleigh McEnany, haven’t heard that name in years, McEnany was the fourth press secretary in that tumultuous first Trump term, and has somehow parlayed about nine months of sniping at the press from behind the podium into a lucrative career in the neon orange studios of Fox News. She was also Leavitt’s mentor.

 

Alyssa Mastromonaco: In January 2021, Leavitt joined then-Congresswoman Elise Stefanik’s office as communications director. That is a big promotion.

 

Erin Ryan: Unfortunately, that placed Leavitt inside of the U.S. Capitol when the January 6th insurrection happened days later.

 

Alyssa Mastromonaco: Leavitt was understandably shaken up by the violence, like any sane person would be. After the attack was subdued and Joe Biden’s 2020 election victory was certified by Congress, Leavitt shared tweets praising Mike Pence and critical of the rioters, as well as referring to a Capitol Hill police officer who directed insurrectionists away from members of Congress as a hero. She still hasn’t spoken publicly about her experience in the US Capitol that day.

 

Erin Ryan: And those tweets somehow magically vanished from Leavitt’s feed by the time she embarked on her next chapter, running for Congress and losing. In July 2021, the irritating 23-year-old announced her candidacy for New Hampshire’s first district on the same local ABC affiliate that had been her part-time employer in college.

 

[clip of Karoline Leavitt]: I’m running for Congress to protect my home state of New Hampshire, to serve as a conservative fighter in a conservative firewall down in Washington, D.C.

 

Erin Ryan: To see how much she’s changed her face.

 

Alyssa Mastromonaco: Yeah, but not her lingo.

 

Erin Ryan: No. From there, she embarked on a media blitz, hitting the Fox News flagship channel from what appeared to be another Tim and Eric level set. Now, New Hampshire’s first district is not that significant, nationally speaking, and the odds were long. Leavitt was up against nine other candidates for the GOP nomination, including another former Trump administration employee, a smarmy college Republicans type named Matthew Mowers. Whom Trump had endorsed when he’d run for the seat in 2020.

 

Alyssa Mastromonaco: Early polling showed Leavitt only netting 7% of the vote among the primary field. In politics, we refer to those numbers as not good.

 

Erin Ryan: But here’s the thing that Leavitt had going for her. As a young, perky blonde woman who talked like a scared, angry old man, she was catnip for the MAGA media, and Karoline hustled to get eyeballs on her. She appeared on pretty much any podcast that would have her, including Steve Bannon’s War Room podcast, several times over. And that’s how she became one of his favorites.

 

Alyssa Mastromonaco: Still, Leavitt was having trouble rising to the top. So now ask yourself, what would Tracy Flick do? First, work her ass off. The Politico profile of Leavitt claims that she went to Manchester every day and knocked on doors from mid-afternoon until it got dark, totaling a dizzying 78,000 doors.

 

Erin Ryan: That’s so many doors. Years later, one of her funnier lies would be that her boss, President Donald Trump, always had a large bruise on the back of one of his hands because of how many handshakes he gave. Now, by that logic, after knocking on 78,000 doors, Karoline Leavitt should have had hands that looked like purple baseball mitts from all the knocking, but she didn’t. Anyway, so the second answer to the question, what would Tracy Flick do, is bring other people to the bottom. In the film Election, Flick rips down her competitor’s campaign posters after being driven to the brink of a nervous breakdown by increased competition from the other two candidates in the race for student government president. In Karoline Leavitt’s story, she flies down to Mar-a-Lago and rather than asking for her former boss’ endorsement, she asks President Trump to not endorse anyone in her race.

 

Alyssa Mastromonaco: Clever girl. She knew that she didn’t have the numbers to support a full-throated endorsement and Trump hates losers.

 

Erin Ryan: Prior to the Mar-a-Lago meeting, she had been doing some very important sucking up for an audience of one. Leavitt had been the most vocal candidate in the primary field to latch onto the big lie that the 2020 election was stolen from President Trump. Her slavish devotion to Trump’s favorite falsehood, and probably also his weakness for blousy blondes, was enough to convince him to refrain from endorsing in the race for Republican nomination in New Hampshire’s first district, and so Karoline’s hopes remained alive.

 

Alyssa Mastromonaco: All this big lie touting was rich coming from someone who was physically in the Capitol when rioters who believed said lie had reigned violence and terror on the building’s inhabitants and who had tweeted in support of Mike Pence and the bravery of the Capitol police in the days after the mayhem.

 

Erin Ryan: A little fib about a whopper, Leavitt is like a Matryoshka doll of lies. Now here’s another Leavitt lie, during the campaign she repeatedly bragged that her parents worked their way up from nothing and got no handouts ever. She told a local newspaper called the Eagle Tribune, quote, “my dad came from nothing and worked his way up, created a successful business that my brothers now work at. He didn’t take any handouts from anyone. He reminds me of President Trump. He says what he believes.” She also made that claim in a video on her campaign website. One of her favorite bugaboos was the so-called socialism of Biden’s Inflation Reduction Act.

 

Alyssa Mastromonaco: Except that wasn’t the truth. You see, according to WMUR, a local New Hampshire TV station, her parents gladly accepted a handout from the federal government during COVID. Quote, “Data compiled from the U.S. Small Business Administration show the company received $250,635 in two Paychecked Protection Program loans in February and April 2020, as well as two economic injury disaster loans totaling $160,000 also in April 2020.” End quote.

 

Erin Ryan: Hmm. Well, you know what we say on This F*cking Guy, it’s not socialism if it helps white people. As the primary grew closer, Leavitt kept appearing on whatever right-wing freak’s podcast would have her. This gave her national reach and allowed her to raise a ton of money from an important donor base, Fox-pilled middle-aged dudes in places far from New Hampshire. In the first 48 hours of her race, she raised over $100,000 and the money kept rolling in from the uncles everybody hates to see coming on Thanksgiving. Overall, her campaign raised $3.8 million.

 

Alyssa Mastromonaco: Sounds like she was great at raising money.

 

Erin Ryan: Well, kinda. We’ll come back to that in a second. Leavitt has always been adept at jujitsu-ing her weakness into strength. One pivotal moment during the campaign was what is now known as the hoebag ad, which was put together by a pack supporting Mowers.

 

[clip of advertisement]: I’m Karoline Leavitt. / Yep, that’s her. Leavitt pretends she’s a conservative, but really, she’s just a woke Gen Z-er. Worships Fauci’s mask mandates, records everything. Listen up, hoebags. Wants to bring her generation’s new vision to Congress. You know, mooching off her parents, running up huge credit card debt. Woke, immature, and irresponsible. Karoline Leavitt for Congress? No, not a chance. Defending Main Street is responsible for the content of this advertising.

 

Erin Ryan: Woke, Immature, and Irresponsible would be a great tagline for a show that I would watch. [laughter] It’s true that Leavitt did rack up quite a bit of credit card debt on her financial disclosure form, she admitted that she had between $10,000 and $15,000 outstanding. But Leavitt kind of leaned into the accusations the ad made about her. Every age-based attack gave her more fodder to claim that she was both an aggrieved victim and a fearless conqueror.

 

Alyssa Mastromonaco: Straight from the GOP playbook.

 

Erin Ryan: Leavitt’s loudly courting the most far-right voters in the Republican primary, combined with her semi-underhanded quest for Trump to withhold his support from her opponents, combined with her psychotic willingness to do whatever it took to get herself in front of as many voters as possible, paid off. She pulled off a surprise victory in the primary.

 

[clip of Karoline Leavitt]: Our conservative voices cannot be silenced, and the future of our beautiful, great, live-free-or-die state is ours.

 

Erin Ryan: The night she won the primary, she was approached by two interviewers, including local reporter Steven Porter. One of the interviewers pressed her about the 2020 election denialism, which she had thrown herself head first into in order to be the most MAGA MAGA to ever MAGA. Leavitt reiterated her commitment to the belief that Joe Biden hadn’t actually won the 2020 elections. Porter followed up by asking her how she could be sure that she’d actually won the primary then, if elections are so prone to fraud. Leavitt ended the interview abruptly and stormed off. The Leavitt flounce was born.

 

[AD BREAK]

 

Alyssa Mastromonaco: Unfortunately, her primary momentum wouldn’t carry her through the general. Recall that 2022 was the red wave election that turned into more like light spotting. Republicans everywhere underperformed expectations. Leavitt ended up losing handily to Democratic incumbent Chris Pappas. This even after she’d spent the months leading up to the general accusing him of a veritable casserole of right-wing scare words, woke a socialist, a secret left-wing extremist!

 

Erin Ryan: Oh well, if at first you don’t succeed, brush yourself off and try again, right? Although that gets a little harder when some of the dust you accumulated in your fall includes more than $300,000 in contributions that exceed legal limits.

 

Alyssa Mastromonaco: That’s right, Leavitt’s army of horny 57-year-old war room fans didn’t strictly adhere to federal campaign finance laws.

 

Erin Ryan: But rather than refunding the illegal donations, Karoline’s campaign spent it, which left Karoline for Congress in debt to those entities to whom it owes refunds. FEC reporting showed that years after the 2022 election faded into the rearview, the campaign still owed $326,000 to more than 100 entities, both donors who made illegal contributions and some vendors that hadn’t been paid for services rendered. As of 2025 to 2026, she’d only paid a little of it back.

 

Alyssa Mastromonaco: Where’d the debt go? It just kind of went away, we guess?

 

Erin Ryan: I don’t know. Where could it go? Good news, though, for a 20-something girl who needs lots of money. During her campaign, she met a rich old guy who wanted to fuck her.

 

Alyssa Mastromonaco: She’s like a fairy tale.

 

Erin Ryan: Nicholas Riccio was a real estate guy who was older than Karoline Leavitt’s dad and looks kind of like a composite photo of every white man on a pontoon boat in Lake Havasu. And by real estate, guy, I mean, he is to real estate what DJ Pauly D is to the symphony.

 

Alyssa Mastromonaco: Yeah, Nick Riccio is a landlord. He owns a bunch of rental buildings in Hampton Beach, New Hampshire, a vacation town widely known to be overcrowded and trashy, kind of like the Lake Havasu of New Hampshire.

 

Erin Ryan: But passive income is passive income, and there’s nothing more irresistible to an ambitious middle-class blonde than the prospect of being able to afford Louis Vuitton purses that aren’t Canal Street knockoffs. Under these favorable conditions, Karoline and Nick fell in love. In December 2023, they announced their engagement.

 

Alyssa Mastromonaco: On the podcast Pod Force One, hosted by somebody named Miranda Devine, whom I was shocked to discover is not a magazine drag queen, Leavitt acknowledged that her relationship was unconventional but defended it by saying that men her age simply lack the maturity of her partner.

 

Erin Ryan: The next month, in January 2024, Leavitt took a job as the National Press Secretary for Donald Trump’s presidential campaign, and her life is on a rocket ship to bullshitopia from there. She even appeared in a Project 2025 training video.

 

Alyssa Mastromonaco: Project 2025, the Heritage Foundation packet of policy ideas designed to streamline America’s descent into a Christian nationalist hellscape, which Donald Trump pretended to know nothing about until he was elected and started enacting the whole thing.

 

Erin Ryan: Now Alyssa, this is perhaps the rudest joke I’ve ever written in this series.

 

Alyssa Mastromonaco: Alright.

 

Erin Ryan: But it begs to be told. Between President Trump and her geriatric husband, Karoline Leavitt is the Michael Phelps of gargling old guys’ balls.

 

Alyssa Mastromonaco: That’s 23 hold medals for her, as press secretary to Trump, she zipped around the country defending the ramblings of her old, rapidly mentally deteriorating boss.

 

Erin Ryan: That is, until this summer, when she took some time away from the campaign to give birth to her son.

 

Alyssa Mastromonaco: Wait, wait, wait. Isn’t Karoline Leavitt a devout Catholic?

 

Erin Ryan: Yes.

 

Alyssa Mastromonaco: And she wasn’t married in July 2024?

 

Erin Ryan: No, not yet. She was just engaged.

 

Alyssa Mastromonaco: And that’s when she gave birth?

 

Erin Ryan: Yes.

 

Alyssa Mastromonaco: But isn’t that against Catholic doctrine to have sex outside of marriage?

 

Erin Ryan: Yes.

 

Alyssa Mastromonaco: Then how’d she get pregnant?

 

Erin Ryan: Such a good question. I guess we’ll ever know. So in July 2024 at 27 years old, Leavitt gave birth to her son, Nico, which makes her baby closer to her age than she is to the age of her husband.

 

Alyssa Mastromonaco: Nico Riccio will be graduating high school when his dad is almost 80.

 

Erin Ryan: A little over a year later, Leavitt would deliver a sanctimonious eulogy of Charlie Kirk wherein she praised the late podcaster for, quote, “Encouraging young people to get married and have children. And as a young person who has done it, I encourage you to it as well.”

 

Alyssa Mastromonaco: She had her child out of wedlock, like a year before she gave that speech, her son was six months old when she got married.

 

[clip of Karoline Leavitt]: Charlie preached a message of faith to all who would listen. He encouraged young people to get married and to have children. And as a young person who has done it, I encourage you to do that as well. It is the best thing in life. It is ultimate legacy that we can leave.

 

Erin Ryan: Uh, get married and have children in that order, Karoline? In that order? And days after Leavitt gave birth out of wedlock, President Trump was shot in the ear in an assassination attempt in Pennsylvania. And as Karoline tells it, she just couldn’t stand by and care for her newborn infant at such a pivotal moment in American bullshit. Lucky for Karoline, the man who knocked her up had the time and bandwidth to help her care for baby. Her mom pitched in as well, quitting her job at a yoga studio to help Karoline take care of little Nico. Second on her mother’s priority list. And Karoline Leavitt went back to work three days after giving birth. Now, this sounds harsh, but I have to point out here, hypocrisy alert, hypocrisy, alert. It is totally fine for a woman to decide that her career is more important long-term than devoting all of her time and attention to infant care. Like, totally fine for a women to want to go back to her after giving birth. I have no judgment. And some people want to stay home with their babies for the first year or longer, both courses of action can be in the best interest of a woman and her family. It’s a little tedious to me when a woman only takes three days to bond with her infant before returning to the urgent matter of their job, does so in service of an ideology that preaches that the most important thing a woman can do is subjugate herself to wifehood and motherhood. Leavitt is a hypocrite. She’s married to an old guy who basically functions as both her sugar daddy and her wife. She’s able to do her job because of her non-traditional marital arrangement. She was pregnant before she got engaged. She gave birth before she was married. She is not an example of doing things the way that she and other figures on the right would call the right way.

 

Alyssa Mastromonaco: Wife and sugar daddy combined into one. She’s really got the best of both worlds.

 

Erin Ryan: We do not have to hand it to her. [laughter] Here’s a quote she gave to the Conservateur, quote, “It would have been a lot easier for me to respectfully decline this job offer and enjoy the past year in the peace and of my previous job. But I know I’m doing it for a bigger cause, to win this election.” The profile mentions admiringly that her son smiles when he hears her voice on the TV and quote, “recognize his mommy during an appearance on Newsmax.” That’s the most Don Draper shit I’ve ever heard. I guess motherhood is the most important thing a woman can do, unless of course, Donald Trump asks you to do something else. Karoline Leavitt finally made an honest man of her baby daddy in January, 2025, days before Donald Trump was inaugurated for the second time. And as soon as that happened, she became the youngest press secretary in history. She helped assuage people’s discomfort with her age-gap marriage and her youth by immediately visibly aging 15 years.

 

Alyssa Mastromonaco: During her first press conference, Leavitt got off to a roaring start, defending Elon Musk’s Department of Government Efficiency, or DOGE, for cutting waste. One particular program she spotlighted included that the government was spending 50 million taxpayer dollars to fund condoms in Gaza.

 

Erin Ryan: Now, fact-checkers and thing-knowers were puzzled by this claim. What on earth could she be going on about? And then a few days later, it became clear the funds weren’t going to buy condoms for Palestinian rebels. The Gaza she was alluding to was actually the Gaza province in Mozambique, which is about 5,000 miles away from the nearest member of Hamas, and the $50 million was earmarked for generalized STI prevention, not specifically condoms.

 

Alyssa Mastromonaco: So the entire thing was both stupid and a lie.

 

Erin Ryan: Yes. Combining stupidity and lying are kind of her trademark. Like when she claimed that the White House is a champion of the First Amendment at the same time that her boss has called for TV networks to have their licenses revoked and threatened the legal status of people critical of Israel.

 

Alyssa Mastromonaco: Remember how she had the Associated Press’s credentials revoked because they refused to refer to the Gulf of Mexico as the Gulf of America after President Trump said he wanted to rename it?

 

Erin Ryan: Pepperidge Farm remembers. [laughter] She claimed that Trump is the hardest working man in politics despite golfing at every opportunity.

 

Alyssa Mastromonaco: She really went to the map for Trump’s very stupid tariffs plan, even after people who can do math pointed out that the math behind them didn’t make any sense. And when called out for being an idiot, she wraps herself in righteous indignation.

 

[clip of reporter]: I’m sorry, have you ever paid a tariff? Because I have, they don’t get charged on foreign companies, they get charged on the importers.

 

[clip of Karoline Leavitt]: And ultimately, when we have fair and balanced trade, which the American people have not seen in decades, as I said at the beginning, revenues will stay here, wages will go up, and our country will be made wealthy again. And I think it’s insulting that you’re trying to test my knowledge of economics and the decisions that this president has made. I now regret giving a question to the Associated Press. Mary.

 

Erin Ryan: She’s argued against birthright citizenship, which is expressly guaranteed by the Constitution.

 

Alyssa Mastromonaco: Although our bought and paid for Supreme Court might have something to say about that.

 

Erin Ryan: TBD. She’s also claimed that Trump has been a great ally to Europe, despite the fact that his decades-long game of footsie with Vladimir Putin has probably paid for grad school for every cardiologist’s kid who treats European leaders.

 

Alyssa Mastromonaco: She also made the odd and illiterate claim that Attorney General Pam Bondi has the power to fire judges just because she is their boss.

 

[clip of Karoline Leavitt]: Foreign terrorists have no legal protections in the United States of America, and this administration is going to continue to deport foreign terrorists and illegal criminals from our nation’s interior.

 

[clip of reporter]: But a judge ordered that he should remain in this country. So, are you saying that it is okay to ignore a judge’s ruling if you don’t like it?

 

[clip of Karoline Leavitt]: Uh, who does that judge work for? It was an immigration judge who works for the department of justice at the direction of the attorney general of the United States, whose name is Pam Bondi, who has committed to eradicating MS-13 from our nation’s interior.

 

Erin Ryan: Correction, whose name was Pam Bondi. That is so dumb. By March, 2025, less than two months after taking the job as press secretary, Leavitt had already surpassed previous press secretary Jen Psaki’s total for PolitiFact noted lies. She’s also claimed that all undocumented people are criminals and, stupidly, that France should be grateful to America for the fact that they’re not speaking German. Unlike her predecessor, Sarah Huckabee Sanders, who the press seemed dead set on treating with the condescending preciousness, usually aimed at a special ed student elected to prom court, the press corps seemed less reserved about aiming its ire at Leavitt. And usually, that’s exactly where she wants to be. The girl loves to get in the mud. Karoline Leavitt is a face and mouth of the Trump administration, and you can tell a lot about how she feels about herself by what she projects. Trump also had some comments about her looks that managed to be both weird and gross.

 

[clip of reporter]: If you don’t want to answer this, I didn’t realize she’d be in the room, but she’s on my list. Karoline Leavitt.

 

[clip of Donald Trump]: She’s become a star. It’s that face, it’s that brain, it those lips, the way they move, they move like she’s a machine gun. Is she in the room?

 

[clip of reporter]: She’s in the room.

 

[clip of Donald Trump]: She’s a star, and she’s great. She’s great person actually, but she’s, I don’t think anybody has ever had a better press secretary than Karoline. She’s been amazing.

 

Alyssa Mastromonaco: It’s just, ugh, yuck. Leavitt’s Instagram account more closely resembles that of a looks-obsessed influencer than that of serious political person.

 

Erin Ryan: Also in late 2025. When she was featured in a photo spread for a Vanity Fair feature on the boss behind her boss, White House Chief of Staff, Suzy Wiles.

 

Alyssa Mastromonaco: I remember this spread. What a glorious news cycle that was. Photographer Christopher Anderson captured several Trump 2.0 figures like Stephen Miller and Marco Rubio and our girl Karoline in his trademark style, up close, unvarnished how he saw them rather than how they wanted to be seen. The photo that made the biggest splash was this extreme closeup of Karoline Leavitt tight on her prematurely stressed and under hydrated skin and close enough to reveal a smattering of messy track marks from receiving lip injections. Too close to the date of the photo shoot.

 

Erin Ryan: Those lips are filled to within an inch of their tiny little lives. Anderson has since said in interviews such as one he did on journalist Jim VandeHei’s podcast that he didn’t intend to humiliate her, nor does he humiliate any of his subjects. Rather, he simply wanted to reveal something. Well, mission accomplished. He revealed that Leavitt, as most of us watching from home can glean, is a deeply insecure person who has signed her life away to an ideology that demands a certain esthetic from women, an esthetic that nobody embodies naturally. The only way for a medium-cute girl from New Hampshire to live up to it, even in the springtime of her youth, is to mangle her own face. The track marks betray a compliance so complete that it submits to demands for self-mutilation.

 

Alyssa Mastromonaco: Even when that self-mutilation is something that is not advised for pregnancy.

 

Erin Ryan: That’s right. A month after the Vanity Fair feature went live, Leavitt announced that she was pregnant again with a child due in May 2026, which would have made her at least a couple months pregnant at the date of the photo shoot. Now is it possible she didn’t know? I mean, maybe, but she’d already had a kid, and any woman who has had one child can tell you that it’s pretty hard to not recognize the symptoms of being in first trimester, the second time around.

 

Alyssa Mastromonaco: Injectors and estheticians can lose their license for knowingly injecting a pregnant person since there isn’t data to prove that it’s safe to receive lip injections or Botox during pregnancy. So somebody should be in trouble here.

 

Erin Ryan: We’d be remiss at this point if we didn’t dunk on the fact that Karoline Leavitt apparently cannot cook. [laughter] Check out her dry ass Thanksgiving spread.

 

Alyssa Mastromonaco: We’ve thoroughly roasted this sad little meal on an episode of Hysteria, but not as thoroughly as Karoline roasted that turkey.

 

Erin Ryan: Thank goodness Karoline has a wife, otherwise she would never eat.

 

Alyssa Mastromonaco: In 2026, despite being more and more pregnant every day, Leavitt’s bullshit has not slowed down. She’s bullshitting for two.

 

Erin Ryan: Leavitt defended the actions of CPB officer Jonathan Ross after he shot and killed American citizen Renee Good on the streets of Minneapolis and called her a fucking bitch, referring to Good as a lunatic woman.

 

[clip of Karoline Leavitt]: This administration will continue to stand wholeheartedly by the brave men and women of ICE, including that officer in Minneapolis who was absolutely justified in using self-defense against a lunatic who was part of a group, an organized group, to interject and to impede on law enforcement operations.

 

Alyssa Mastromonaco: Maybe her lowest moment.

 

Erin Ryan: I mean, I definitely think that one’s going on Satan’s highlight reel for where he like when he’s reviewing tape to be like, who gets into hell next.

 

Alyssa Mastromonaco: Like, here’s the fast pass.

 

Erin Ryan: Yeah, that definitely made the reel.

 

Alyssa Mastromonaco: She brilliantly shared a poll showing a hundred percent MAGA approval rating.

 

Erin Ryan: MAGA supporters supporting MAGA. More news at 10. At the beginning of Lent, Karoline got into it with the pope because he refused to participate in Trump’s bullshit board of peace.

 

Alyssa Mastromonaco: She’s declared the completely unresolved fallout from the Jeffrey Epstein case to be resolved, urging Americans to move on from the massive pedophile ring involving high-level members of government, society, and academia.

 

[clip of Karoline Leavitt]: What I’m telling you is that what President Trump has always said is that he kicked Jeffrey Epstein out of his Mar-a-Lago club because Jeffrey Epstein was a creep, and that remains true. And this call, if it did happen, corroborates exactly what President Trump has said from the beginning. And I’m sure many of you, when you read that alleged FBI report, probably thought to yourself, wow, this really cracks our narrative that we’ve been trying to push about this president for many years. So we’re moving on from that.

 

Alyssa Mastromonaco: In January, Leavitt did another weird thing. She ended her press conference just seconds before it hit the 65-minute mark, suddenly trailing off and darting off stage in a way many people found strange.

 

[clip of Karoline Leavitt]: So I would encourage everyone to take a look at the website. It’s quite well done. And thank you all very much. It’s great to be back with you.

 

Erin Ryan: This led many onlookers to suggest that Leavitt had done this because the Kalshi prediction markets had determined a 98% likelihood that the press conference would go on for more than 65 minutes. And her behavior was consistent with somebody who was insider trading on a press conference that they ran. Somebody made a bunch of money because that press conference did not hit 65 minutes! Wow!

 

Alyssa Mastromonaco: Wow.

 

Erin Ryan: Yeah, literally seconds to spare. At least she’s sticking to the important business of managing comms during wartime and economic uncertainty, like making Getty take down unflattering photos of her from their database. In March, Oliver Darcy reported that this photo of Leavitt, her son, and a turkey taken from below the stage in the press briefing room had been removed because the White House didn’t like it. You’ve heard of the Streisand effect.

 

Alyssa Mastromonaco: You’re a calm person, come on.

 

Erin Ryan: But there is no joy in Mudville, even after years of copy pasting Trump’s brain into her mouth. Now there are signs that Trump may be displeased. On March 31st, Trump lamented his cratering poll numbers, noting, maybe Karoline is doing a poor job.

 

[clip of Donald Trump]: I got 93% bad publicity. Some people say 97, but between 93 and 97. A person that gets 97% of bad stories, maybe Karoline’s doing a poor job, I don’t know. She’s my representative, you’re doing a terrible job. Should we keep her? I think we’ll keep her.

 

Erin Ryan: Don’t worry, Karoline, I’m sure your loyalty to a man who has never been loyal to anybody or anything in his life will pay off. What will you do when he’s gone? Have an original thought of your own? We’ll believe that when we see it. So there you have it, Alyssa. Karoline Leavitt. Where do you think she lies on our matrix of fucking guys?

 

Alyssa Mastromonaco: Well, Erin, as Karoline would say, what a stupid question. I feel like I’d be doing this MAGA wunderkind and White House press secretary a disservice if I did anything less than put her at scheming sociopath and true believing zealot. She’s packed a lot into less than 30 years.

 

Erin Ryan: I think she’s a dumb ass though, Alyssa.

 

Alyssa Mastromonaco: Do you think she is a dumbass?

 

Erin Ryan: I don’t think it, she’s very adept at like just firing away bullshit, but like imagine her on the witness stand. I think like a truly intelligent person could manage being like on a witness stand where they’re actually accountable. But like in a press conference, she’s not really like being held accountable. And in interviews I’ve seen her do, she’s like getting pushed back on really.

 

Alyssa Mastromonaco: That’s fair.

 

Erin Ryan: The power differential allows a true dumbass to succeed as White House press secretary.

 

Alyssa Mastromonaco: You know what? I think I let her have too much Trac— I let Tracy Flick shine too bright on Karoline.

 

Erin Ryan: That’s true, because Tracy Flick is like an intelligent character.

 

Alyssa Mastromonaco: She’s a scheming sociopath.

 

Erin Ryan: She’s scheming a sociopath, I think she’s a true believing zealot. If she started that way, I’m not sure, but I think at this point, she’s like, yes, Donald Trump is my god, and I will do whatever it takes for him. So I do think that like when Trump is gone, I don’t know if she can generate her own thoughts.

 

Alyssa Mastromonaco: It’s fair enough. All right, that about wraps up the time we have for this episode of This F*cking Guy. If you like what you’ve seen, hit subscribe, share with your friends, and leave us a comment. If you’ve got an idea for a future fucking guy, we should spotlight.

 

Erin Ryan: This episode was written and researched by me, with a writing assist from Alyssa Mastromonaco. All the rest of the credits, as well as links to our sources, like Adam Wren’s work at Politico, can be found in our show notes. Trust me guys, the bibliography is always a fun read. Take care, be well, remember that old man’s sperm is hazardous to your health.

 

Alyssa Mastromonaco: And fuck that guy. [music plays]