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Donald Trump Jr: Everything You Didn’t Know About His Sh*tty Past

Hysteria | November 9, 2026



In our 51st episode of This F*cking Guy, Crooked’s Jane Coaston joins to dive deep into the past of the scumbag spawn, Donald Trump Jr. From his “Diaper Don” partying days to his failed business ventures, from his penchant for hunting endangered wildlife to his incessant shit-posting, from his election meddling to his gross behavior with women, this guy may just be as big of a loser as his dad!

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CHAPTERS
00:00 – Intro
01:26 – Early life & relationship with family
14:12 – Failed business ventures
18:43 – Relationship with Aubrey O’Day
20:35 – Ad Break
23:10 – 2016 Trump Campaign & Presidency
30:04 – Relationship with Kimberly Guilfoyle
32:44 – 2020 Trump Campaign
37:35 – 2024 Trump Campaign & Presidency
42:10 – Future Political Career?
43:30 – Matrix rating & Outro

Sources: https://docs.google.com/document/d/1TpqJ07FTtZj6C7rjOJLaSbBkiS4FmsKwPl0SdoPhmNY/edit?usp=sharing

For a transcript of an episode of Hysteria, please email transcripts@crooked.com.

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.

That’s it. End of mission.

Learn more about us at crooked.com

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Written by Hysteria

Comments

This post currently has 42 comments.

  3. @necromunda_dave

    November 9, 2026 at 11:25 am

    Awesome episode!
    I recommend doing an episode on Asmongold, a streamer and youtuber who is responsible for spreading and popularizing some of the Trump Admin's most foul shit among younger viewers.

    Reply
  4. @SebBrosig

    November 9, 2026 at 11:25 am

    "Andrew Tate getting arrested" costume? We love it when you go for that extra-feminine look!
    Still waiting for that Andrew Tate TFG episode, maybe it's just too much of a crowded field for Tate to make the grade.

    Reply
  7. @JosefGololo-Lo-m9p

    November 9, 2026 at 11:25 am

    4:34 i know, its Just a sidenote, but couldnt the "it" referring to the children be a language Thing? I dont speak slovanian. But a child in German is also referred to as "it" (es) as well, due to "das Kind" being of neutral grammatical gender. (Funnily or maybe Not so funny girls, Mädchen, is also of neutral gender, because it derived from Magd with a chen diminutive which makes everything neutral, therefore means little Woman, but i digress)

    Reply
  21. @stephaniefromthenetherland8748

    November 9, 2026 at 11:25 am

    Americans will elect this Don Jr as US president some day. Now that they flipped to the Democrats they think they found the cure to their Trump hangover. Once they'll see that politics and change is hard, they'll go back to using again and end up with a headache..again. Meanwhile leaving the rest of the word suffering and despising the country for their irate behavior. Thanks US for being addicted to power instead of trying to be the happiest country in the world. You are probably in denial that the world has given up on you and your addictions. Continue podcast like this, interventions like like these are at least a way to keep the country sober and the rest of the world a safer space.

    Reply
  28. @feebeedoc78

    November 9, 2026 at 11:25 am

    Look, I get the intention of this and mostly I agree. But could you tone down the "hysteria". The loud high pitched tones and cadence is just unpleasant to the ear. From a non-American.

    Reply
  39. @HuntClubBarbee

    November 9, 2026 at 11:25 am

    Doubt Trump has large balls which explains why he spends so much time focusing on "big, strong, powerful men". As he just shared with us last week: "I LOVE THE MEAT! followed by obscene hand gestures and glugging sounds. Make of that what you will.

    Reply

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