Podcast Summary: Countdown with Keith Olbermann
Episode: RERUN: COULD TRUMP PASS A SANITY TEST? - 10.3.25
Date: October 3, 2025
Host: Keith Olbermann
Overview
In this rerun episode, Keith Olbermann revisits his seminal Vanity Fair article from July 21, 2016—"Could Trump Pass a Sanity Test?"—to explore its enduring relevance as Donald Trump remains a dominant force in American politics. Olbermann reads much of the original article aloud, updated with 2025 asides, applying the Robert D. Hare Psychopathy Checklist to Trump’s public behaviors. The episode blends sharp political commentary, dark humor, and psychological analysis, concluding that by clinical metrics Trump would likely be diagnosed as a psychopath.
Key Discussion Points & Insights
The Enduring Relevance of Trump’s Mental Fitness
Timestamps: 02:14–04:30
- Olbermann opens with the notion that future historians will be shocked at “how long it was clear this man was mentally incompetent and nobody did anything about it.”
- He notes raising these concerns in 2016, on Chelsea Handler’s show and in the original Vanity Fair piece.
- Draws attention to the normalization and proliferation of questioning political figures’ mental health, especially given Trump’s own history of doing so to rivals.
The Hare Psychopathy Checklist: Structure and Rationale
Timestamps: 05:30–08:58
- The test, developed by Canadian psychologist Robert D. Hare, scores twenty criteria 0–2 points each.
- In the US, a score of 30 or more suggests psychopathy.
- Olbermann explains key psych terms (“sociopath” vs “psychopath”) with vivid analogies (Ted Kaczynski vs. Ted Bundy).
Scoring Trump, Item by Item
1. Superficial Charm
Timestamps: 08:58–10:30
- Trump’s conflicting personalities—quiet in private, bombastic in public—“should by itself preclude one from having access to multiple nuclear warheads.”
- “He fooled Bill Maher. So if you’re giving out points about fake charm, Trump gets both of them.” (10:25)
2. Excessive Sense of Self-Worth
Timestamps: 10:31–11:55
- Trump’s infamous boast: “I feel like a supermodel...except like times 10.” (11:00)
- Olbermann ridicules Trump’s appearance and self-aggrandizement.
3. Need for Stimulation / Proneness to Boredom
Timestamps: 11:56–12:52
- Trump’s business ventures and refusal to take vacations cited as evidence for “inability to sit still.”
4. Pathological Lying
Timestamps: 12:52–13:56
- Example: Trump reverses his comments on armed patrons in the Orlando Pulse shooting, then gaslights via Twitter.
- “Can I stop here or should I walk you through the hot and cold running lies alternating with the admissions...?” (13:15)
5. Manipulative Behavior & Conning
Timestamps: 13:56–14:16
- Olbermann sarcastically offers Mike Pence or Ivanka as guest essayists for this.
6. Lack of Guilt/Remorse
Timestamps: 14:16–16:38
- Trump refuses to ask God for forgiveness: “I’m not sure I have...I don’t bring God into that picture. I don’t.” (15:00)
- Highlights hypocrisy towards religious convictions of others.
7. Shallow Affect (Emotional Depth)
Timestamps: 16:41–18:56
- Trump fails to recognize insults, e.g., misreads Billy Joel’s sarcastic “shout-out.”
- Cites Trump’s odd claim about jinxing Derek Jeter’s career.
8. Lack of Empathy
Timestamps: 18:57–20:05
- After Pulse shooting, Trump tweets: “Appreciate the congrats for being right on radical Islamic terrorism. I don't want congrats...” (18:58)
9. Parasitic Lifestyle
Timestamps: 20:10–22:09
- Trump’s penchant for slapping his name on others’ work (real estate ventures, steaks, vodka, etc.).
10. Poor Behavioral Controls
Timestamps: 22:15–22:53
- Olbermann’s 2016 optimism that “everybody agrees he’s going to dial it all back this time” aged poorly, with Trump serially failing to do so.
The Halfway Mark—Scoring Recap
Timestamp: 22:53
- “So far, he’s been graded for a possible 20 points and he has 20 points the rest of it.”
Second Half of the Checklist
11. Sexually Promiscuous Behavior
Timestamps: 26:58–28:55
- Chronicles Trump posing as “John Miller” to boast about sexual conquests.
12. Early Conduct Problems
Timestamps: 28:56–32:01
- Trump, by his own admission, punched a music teacher in second grade, earning a black eye: “The only argument against calling this early behavior problems is that the first word implies that it stopped at some point.” (32:02)
13. Lack of Realistic Long-Term Goals
Timestamps: 32:02–34:25
- Olbermann refuses to score this as a deficit: “He became president. So on this one, Trump, you’ll get nothing and you’ll like it.” (34:20)
14. Impulsivity
Timestamps: 34:25–35:34
- References Trump discussing his genitals during a debate and crude public insults—textbook impulsivity.
15. Irresponsibility
Timestamps: 35:34–36:51
- Offers multiple overlapping examples (refusing to acknowledge McCain’s military sacrifice, financial irresponsibility, etc.), conservatively scores one point.
16. Failure to Accept Responsibility for Own Actions
Timestamps: 37:13–37:53
- When confronted with evidence about veteran fundraiser money, Trump dodges or hangs up.
- “Trump simply hung up the phone.” (37:48)
17. Many Short-Term Marital Relationships
Timestamps: 37:53–39:00
- Trump has had three marriages, of substantial length; Olbermann does not score this item.
18. Juvenile Delinquency
Timestamps: 39:00–41:00
- Headlines from Trump’s childhood: bullying, violence at military school, physically aggressive behavior toward peers and adults.
19. Revocation of Conditional Release
Timestamps: 41:00–42:09
- No points awarded; Olbermann notes current legal outcomes might someday justify it.
20. Criminal Versatility
Timestamps: 42:09–43:38
- Ongoing debate with his therapist about the scope: “if you scammed charities, stole money from grandmothers via a phony university...it all qualified.”
- Refers to Trump’s range of legal and ethical scandals.
Final Score and Implications
Timestamps: 43:38–44:00
- Olbermann’s final tally: 33 out of a possible 40.
- The clinical cutoff for psychopathy is 30.
- “You’re a psychopath. The implications are clear.” (43:45)
- Warns that daily scandals might even raise Trump’s score further: “In the time it has taken you to listen to this podcast...he’s probably just done something new to raise his score. Hasn’t he?” (44:25)
Notable Quotes & Memorable Moments
- “It was clear this man was mentally incompetent and nobody did anything about it.” — Keith Olbermann (02:15)
- “As the old joke goes, no pain, no gain. Also, no brain, no pain.” (06:38)
- “If you’re giving out points about fake charm, Trump gets both of them.” (10:25)
- “He is bright orange. He is an old man affecting a hair color and style that would have been rejected by the 80s synth pop group A Flock of Seagulls.” (11:00)
- “I punched my music teacher because I didn’t think he knew anything about music, and I almost got expelled.” — Donald Trump/Olbermann citation (29:30)
- “He could have 26 points. He only has 24.” (32:30)
- “You’re a psychopath. The implications are clear.” (43:45)
- “Even if...the President is unwell, he’s probably just done something new to raise his score. Hasn’t he?” (44:30)
Structure and Tone
Olbermann’s delivery is a mix of sardonic wit, clinical detachment, and political alarm. He anchors each checklist item to a combination of Trump’s public statements or verified behavior, providing context and often a personal anecdote or historical reference for contrast. The episode is both darkly comic and deeply serious, highlighting the intersection of psychology and politics.
Conclusion
Implication:
By the widely used clinical standards, Trump would score above the threshold for psychopathy. Olbermann underscores the absurdity and danger in the ongoing normalization of such behaviors, suggesting that media, political institutions, and the public have failed to grapple with the psychological implications of Trump’s conduct.
Utility:
For listeners unaware of the detailed psychological framework, the episode offers an accessible walk-through of the Hare Checklist applied to one of the most influential and controversial political figures of the 21st century.