The Daily Beast Podcast
Episode: Why Trump, 79, Only Wants Identical Women: Wolff
Date: November 23, 2025
Host: Joanna Coles (Chief Content Officer, The Daily Beast)
Guest: Michael Wolff (journalist, author)
Overview:
This episode delves into Donald Trump’s enduring fascination with surrounding himself with identical-looking women, as observed during his recent criminal trial and throughout his public life. Michael Wolff offers insights on Trump’s personal relationships, his use of women for image management, and the political maneuvering involving the Clintons and the Epstein files. The discussion probes what this obsession reveals about Trump’s character, its political implications, and how such attitudes clash with contemporary expectations.
Key Discussion Points & Insights
1. Trump’s Circle of Women (01:41, 10:46, 13:10)
- Wolff and Coles discuss the phenomenon of Trump being constantly surrounded by younger, attractive women who are styled very similarly—an observation made both publicly and by jurors during his trial.
- The women around him (e.g., Hope Hicks, Madeleine Westerhout, Natalie Harp, Alina Haba) are described as looking and dressing identically, creating a “creepy” effect and evoking past cultural references like “Charlie's Angels” or Robert Palmer’s “Addicted to Love” video.
“There is always an entourage of younger, good looking women around Trump, all dressed the same and all who basically look the same... it really creeped everybody out.”
— Michael Wolff (01:41, 13:13)
- Explanation for this: Trump seeks not only adulation but to project ongoing virility and desirability, especially as he ages and as important women in his personal life (Melania, Ivanka) become more distant.
2. Trump’s Relationships with Women: Politics and Image (11:29, 14:47, 19:40)
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Wolff notes Trump's lifelong obsession with women, from beauty pageants to his history of insults targeting those who don’t fit his ideal.
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Example: The “Quiet, Piggy” insult to reporter Catherine Lucy, highlighting Trump’s continued misogyny.
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Even those with real influence in “Trump World,” like Susie Wiles (his campaign chief in Florida), are subjected to judgments based on appearance:
“She looks like a refrigerator, fire her.”
— Michael Wolff (11:47) -
Discussion acknowledges the political use of women as props, and how this aligns with Trump's desire to be seen as powerful and relevant—regardless of reality.
3. The Clinton-Epstein Distraction (02:37, 05:50, 06:12)
- Any trouble involving Trump and women is often met with attempts to redirect focus onto Bill and Hillary Clinton, especially using the Epstein scandal.
- The House Committee’s subpoenas for the Clintons are described purely as tactics of “distraction and embarrassment,” with no informational value.
- There’s skepticism that files implicating Trump or his allies will ever be fully released, but the show underscores how use of private planes (Epstein’s in particular) became a kind of social currency among power brokers.
4. Lame Duck Status & Loss of Power (28:35, 31:05)
- Conversation shifts to Trump’s inevitable lame-duck period if elected to a second term. Unlike past presidents who recede quietly, the expectation is that Trump will “grab power” audaciously, refusing to accept diminishing relevance.
- The release of the Epstein files without Trump’s consent is viewed as evidence of waning influence—even within his own party:
“Release the Epstein files. Despite anything that he said, despite any arms that he twisted, any of the threats he would surely have been making, they did it anyway.”
— Michael Wolff (29:45)
5. Comparisons: Trump, Bill Clinton, and RFK Jr. (25:52, 34:26)
- Coles and Wolff compare the public’s response to Trump’s misogyny to the past “forgiveness” of Bill Clinton’s behavior, arguing that times have changed and Clinton could not be elected president again today.
- Brief digression into RFK Jr.'s own issues with women, including an upcoming memoir and public controversies.
6. The Melania Question & Crowdsourced Queries (37:44 onward)
- Michael Wolff solicits and discusses questions for Melania Trump in light of a possible subpoena, with listeners suggesting pointed queries about her modeling past, experiences at Mar-a-Lago, and emotional responses to Trump’s behavior.
- The discussion highlights Melania’s aura of unknowability and the likelihood of public narratives conflicting with reality.
Notable Quotes & Memorable Moments
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On Trump’s obsession with identical women:
“It is fundamental to his character...he’s in the women business. Beauty pageants, modeling agencies—this is who he is.”
— Michael Wolff (10:46) -
On distraction via the Clintons:
“Every time Trump is in trouble about women, fundamentally the Epstein story is about women...he goes: Bill Clinton did it more.”
— Michael Wolff (02:37) -
On Trump’s outdated attitude towards women:
“His regard for and relationship with women is unacceptable in this moment in time. He is out of time...a throwback.”
— Michael Wolff (24:41) -
On the nature of power and Trump's likely refusal to fade:
“To be a lame duck means you’re losing power...He grabs power in an audacious way, and so audacious that people give it to him.”
— Michael Wolff (28:35) -
On Melania’s unknowability and reinvention:
“She has an unknowableness about her that lends itself to, to now being her brand.”
— Co-host (14:32)
Pivotal Timestamps for Key Subjects
- Trump’s Entourage of Identical Women: 01:41, 10:46, 13:10, 14:32
- Clinton/Epstein as Distraction: 02:37, 05:50, 06:12
- Susie Wiles anecdote (appearance vs. influence): 11:47
- Melania’s mystery, Amazon documentary, and crowdsourced questions: 37:44–46:23
- Trump’s Lame Duck Status & Power Dynamics: 28:35–33:28
Thematic Wrap & Outlook
The episode paints a portrait of Trump as a man obsessed with projecting an undiminished virility through his associations with younger, identical women—both for personal gratification and public signaling. This image, however, is increasingly at odds with his advancing age, the reality of absent close women in his life, and changing cultural norms. The discussion also explores how Trump reflexively weaponizes the Clinton/Epstein connection as distraction, and how his inability to accept diminished power will define his post-presidency or second term. Listener engagement centers on the enigma of Melania Trump and the complexity of her role in the unfolding narratives.
For Listeners:
This conversation offers a candid, critical, and sometimes darkly humorous look at power, gender, and political spectacle in the Trump era, with Michael Wolff’s characteristic incisiveness and Joanna Coles’ sharp, wry perspective.