Podbit · The Bulwark Podcast
After Kristol's Weekly Standard editorial opposing Trump in 2015, Trump personally called him: jocular, back-slapping, confident he'd come around. Kristol wasn't moved, but he understood in that moment exactly why people get taken in. Con men are good at this — it's how the con works.
Where this was said
At 47:45 · chapter starts 47:40
The episode's closing conversation turns to Trump's interpersonal charm as a political phenomenon. Miller and Kristol discuss why people who should know better get won over by Trump in private settings. Kristol's key data point is his own 2015 phone call: after writing an editorial that Trump could never be supported, Trump called him personally — jocular, back-slapping, confident he'd come around. [1] — Bill Kristol "After Kristol's Weekly Standard editorial opposing Trump in 2015, Trump personally called him: jocular, back-slapping, confident he'd come …" 47:45 Kristol was unmoved, but he understood in that moment exactly how people get taken in. His diagnosis: Trump is a successful con man, and con men are necessarily good at getting people to like them — that's how the con works. He notes that Trump spent the next three years trying to get the Weekly Standard shut down, a reminder that the charm has a menacing underside. Miller adds a sharp observation about political interpersonal strategy: the Trump approach of jocular flattery, even when complaining, is simply more effective than the whining, self-pitying approach of lesser politicians — and politicians of all stripes could learn from it, whatever else they should reject about Trump.
Most people confuse things they value instrumentally (because they get them other things) with things they value intrinsically (for their own sake). Greenberg's friend stayed in a miserable relationship for years because she was living by her parents' values, not her own — the values map made the mismatch instantly visible.
Jungian analyst James Hollis distills a good life to four things: shut up (have gratitude, stop whining), suit up (prepare yourself to fulfill a role), show up (do the actual work in service of others), and daily get out of stimulus-response to ask what your deeper wish actually is. The whole landscape of self-help slots into just these four bins.
Toward the end of their 20s, many men discover that all the strategies that earned them recognition and success have stopped working. It's a second adolescence — more important than the first — where the question shifts from 'how do I play the game?' to 'who do I actually want to become?' Most people going through it look fragile from the outside. They're actually building a foundation.
Boys are told from childhood not to cry, not to feel, not to be weak — but anger gets a pass. The result: a generation of men who reroute every emotion, including sadness and fear, through the only acceptable channel. Emotional avoidance isn't toughness, it's misdirected sensitivity.
Men need a 'bank account' of masculine status — muscle, money, success — before society grants them permission to express vulnerability. Chris Bumstead can cry at the Olympia and get celebrated. A struggling nobody doing the same thing gets contempt. This creates a tragic paradox where the men who most need emotional support get the least of it.
Emotional sensitivity isn't a defect — it's a high-resolution scanner for human experience. Highly sensitive people pick up body language, tone, and unspoken tension that others miss entirely. In the right environment, that's not a liability. It's a superpower.
Her supervisor told her she was too emotional for the pediatric ICU. So she asked herself: 'What area of medicine can I cry in?' That question led her to psychiatry. Finding the environment that holds your emotional sensitivity isn't retreat — it's strategy.
For someone with RSD, ghosting isn't ambiguity — it's a self-verdict. Their brain doesn't read 'this relationship ended,' it reads 'I am the reason this failed.' No closure means the brain fills the gap with evidence of personal insufficiency, and it keeps filling indefinitely.
More freedom doesn't produce more happiness — it produces more anxiety. Kierkegaard identified this 180 years ago: the more options you have, the more you feel the 'dizziness of freedom,' a paralytic unease at having to choose any single one. The freest generation in history is, by his prediction, exactly the most anxious.
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