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Karoline Leavitt: Everything You Didn’t Know About Her Sh*tty Past

Hysteria | August 19, 2026



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!

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CHAPTERS
0:00 – Intro
2:07 – Early Life
5:05 – First TV Appearances
7:42 – Internship for Trump 1.0
9:22 – Post-January 6th Thoughts
10:05 – Failed Run for Congress
17:14 – Ad Break
21:18 – Campaign Loss and Finance Violations
22:37 – Karoline in Love
23:44 – Joining Trump’s 2025 Campaign
27:51 – Press Secretary for Trump 2.0
34:45 – Karoline’s Lowest Moments
38:20 – Rating Karoline Leavitt

Sources: https://docs.google.com/document/d/1IFt8Pb_KlEdnZiCYdOXeeAm8FTQldnvSGbmbtqGnmIQ/edit?usp=sharing

Political commentator and comedy writer Erin Ryan and former White House Deputy Chief of Staff Alyssa Mastromonaco are joined by a bicoastal squad of funny, opinionated women to talk through everything from reproductive rights to romcoms. They break down the political news of the week, plus the topics, trends, and cultural stories that affect women’s lives. New episodes drop every Thursday. Get in touch: hysteria@crooked.com.

Photos courtesy of AP Photo Archive

Crooked Media believes that we need a better conversation about politics, culture, and the world around us—one that doesn’t just focus on what’s broken, but what we can do to fix it. We are a media network that showcases stories, voices, and opportunities for activism that inform, entertain, and inspire action, because it’s up to all of us to do our part to build a better world.

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Written by Hysteria

Comments

This post currently has 21 comments.

  1. @AnthonyDupree-w5l

    August 19, 2026 at 8:52 pm

    Caroline lyrics Caroline livick she just ruined herself Carolyn Leavitt current herself Caroline Levick Caroline living herself well reason I couldn't play sports yeah she played with Donald Trump's Boss 2 yeah I'm pretty sure you ride her too I made it I can't in my name is Anthony Wayne Dupree you don't like Carolina don't like a poor guy don't have and she can she can find her what Carrie Underwood came find her way to go out of Georgia yeah and Carrie Underwood play my was her coming out loud husband you have to live together before your common law husband and wife if Carrie Underwood wants to know you have to live together to be common-law husband and wife well that's one thing I want to put I asked Carrie Underwood how about she come and get me and take me home to the American Idol and I'd sing with her Carrie Underwood said I didn't need to be famous

  3. @mmagnusol

    August 19, 2026 at 8:52 pm

    You should repost this every six months for at least five years. Hopefully potential employers may review this.
    Whatever keeps her out of the public eye forever.

  13. @mecongberlin

    August 19, 2026 at 8:52 pm

    This whole administration is filled with hyper insecure narcissists, which makes them behave like wet cats all the time. That is what Bone Spurs needs. Strange…the vision one once had, thinking USA, like you rather saw Sony Crockett, Rocky, Elvis, Rickles, Sinatra – now it’s Hegseth, Miller, Noem, and so forth…it feels all like the Burton ending in Planet of Apes.

    And she is the youngest trusted advisor now and maybe she will become the youngest and first female president, before she will start building her personal moon base, Queen K. I.

Comments are closed.

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