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Charlie Sykes On The Mob-Boss Presidency
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Charlie Sykes On The Mob-Boss Presidency

The Midwestern conservative helps me grapple with the authoritarian crisis.

Charlie is a journalist and podcaster. From 1993 to 2016, he hosted a conservative talk show on WTMJ in Milwaukee. He was also the editor of Right Wisconsin, the editor-in-chief of The Bulwark, and a commentator on MSNBC. He recently went fully independent with his own substack, “To the Contrary” — subscribe! The author of many books, the latest was 2017’s How the Right Lost Its Mind.

An auto-transcript is available above (just click “Transcript” while logged into Substack). For two clips of our convo — on the Trump admin’s soulless response to the ICE killings, and if the GOP is starting to turn on Trump — head to our YouTube page.

Other topics: growing up in a contrarian liberal home; his dad a journalist prof who ran Eugene McCarthy’s 1968 campaign in Wisconsin; Charlie converting to Catholicism in college; TS Eliot’s influence on his faith; writing his first book based on his dad’s essay against academia; getting into talk radio in the early years; the Limbaugh effect; the MSM disdain over talk radio; my early campaign for marriage equality reaching Charlie’s show; the lost culture of healthy debate; Gingrich’s contempt for the opposition; Vince Foster; Bush discrediting conservatism; the demonization of Obama; the failure of GOP gatekeepers; both parties embracing mass migration; “The Flight 93 Election”; the groups controlling the Dems; Biden empowering Trump on immigration; the Fox News fallacy; the anti-Semite card with respect to Israel and the settlements; Gaza; the war in Ukraine; the ICE killing in Minneapolis; JD’s soulless presser; the indecency of Matt Walsh and Megyn Kelly; the threats to Greenland; the persecution of Jerome Powell; civil war rhetoric; the Caribbean boats and Maduro’s ouster; our Viking foreign policy; Cardinal Dolan embracing MAGA; Pope Leo replacing Dolan; tariffs as protection money; the abuse of the pardon; ICE recruitment ramping up; and how dogs are the best people.

Browse the Dishcast archive for an episode you might enjoy. Coming up: Kevin Williamson on the devolution of the GOP, Jeffery Toobin on the pardon power, Jason Willick on trade and conservatism, Vivek Ramaswamy on the right’s future, and Michael Pollan on consciousness. Please send any guest recs, dissents, and other comments to dish@andrewsullivan.com.

From a fan of last week’s pod with Claire Berlinski:

I knew Claire tangentially during the salad days of blogging. I am so happy for her well-deserved success as a writer and international observer, and I’m grateful for her current commentary on foreign policy. Thank you for bringing her to the Dishcast.

Another listener dissents:

I came away from the episode more frustrated than enlightened. Neither you nor Claire acknowledged the elephant in the room: China. It’s unbelievable that neither of you mentioned the country’s name once during a geopolitical discussion. China supplies Russia with materials, logistics, and North Koreans!

Trump was the first to call out the threat from China a decade ago, and his current international actions are aimed squarely at China: Venezuela, Iran, and yes, Russia. I would have voted for Harris if I lived in the US, but I have to concede that Trump’s international priorities are spot on — and acting in the interests of the US and the democratic world. He’s trying to pacify Putin with the Donbas to end the war and get back to trying to lure Putin away from China.

Neither of you were actually wrong about anything. Yes, Trump probably has dementia. Yes, he’s a shallow thug. Yes, he’s more greedy than he is strategic. Yes, Netanyahu and Rubio are leading him around by the nose. But you have to ask why he’s doing this. Dispensing with conventional wisdom, Trump is the boy who announced that the Chinese emperor has no clothes. He’s the first to admit the unipolar era is over and we’re already in the multipolar era (even if he barely understands either of those terms).

I’m loathe to accuse you of TDS, but I don’t know what else to call it when you insist on such shallow readings of Trump’s underlying motivation. He and his cabinet are aware that China is the enemy. It’s fine that you don’t like him; I don’t like him either. But for the love of God, please accept that Trump and Rubio see China as the true international threat.

Perhaps our listener didn’t hear the full episode, because we did mention China several times. For example, Claire said:

There are very real concerns about national security involved in the Venezuela-Iran-China-Russia nexus. China is now the biggest trade partner that Latin America has. It’s making massive investments in Venezuela from the point of view of trade routes, supply lines, petro dollars. There are a lot of reasons to say we do not want Venezuela acting as a forward operating base for our worst rivals or most threatening rivals. But I don’t think that’s how this administration thinks. I think if anything, Trump has been seduced by the idea of Putin gets Europe, Xi gets China, and we get this hemisphere.

Here’s another clip of the episode — on Rubio:

Another writes:

The episode with Claire REALLY hit home for me, especially the sentiments discussed at the end about Trump and the state of affairs. It gave such validation to the deep dread I’ve been experiencing lately: watching this man destroy, day by day, norm by norm, the country that I have always been so proud to call home.

It’s especially hard to still have family and friends who are still MAGA, even after all we’ve collectively experienced. I am not one of those who “cuts off” my family and friends. I believe family is important and we should nurture and maintain those relationships at all costs. But it’s getting harder and harder to have conversations with them about what is going on in this country, simply because we are operating from entirely different realities. (Reminds me of the college football study from the 1950s where they had members of the Dartmouth and Princeton teams watch the same video of the same game, only to have them each perceive entirely different realities.)

Personally, I’m always checking my blindspots for fear of being labeled with the TDS moniker, but even so, it’s getting harder to try and “steelman” much of the rhetoric and policies currently being defended by MAGA. Rather than engage and debate, I find myself retreating from loved ones with whom I disagree, simply because it so utterly saddens me to see the people I love defend acts I find morally abhorrent. It’s an odd feeling, and one I’ve never experienced before. How do we ever come back from this brink?

I truly believe the root of all that plagues us is the loss of a shared collective experience and some basic sense of shared reality. You may have seen it, but there is a clip of director Ari Aster circulating around the interwebs of late, where he describes this phenomenon as he sees it:

Thank you for all the interesting conversations in 2025 and for continuing to speak up on the important matters for our democracy. Godspeed in 2026.

One more on the Berlinski pod:

As someone who has had to suffer many a Rhodes Scholar in my life, I have searched multiple times for your 1988 piece on Ben Sherwood and never found it. As you mentioned in the latest pod, the piece seems to have been scrubbed from the internet. Is there any chance whatsoever you’d be willing to share it with me in whatever form you might have it yourself? I’m dying to read it.

We linked to the piece in the show notes — here it is, reproduced on the Daily Dish. Speaking of the blog, a longtime reader asks:

Maybe this is an odd question, but is there a hard copy of the Daily Dish and Weekly Dish preserved somewhere in an archive for future generations — even centuries, like the cuneiform tablets of the Hittites — so that when the Internet goes dark or some AI monster swallows it, historians will know what some intelligent writer and readers were thinking and talking about back in that remote 21st Century? Millions of words, lots of pages, and probably not that easy or cheap to preserve, but it would be great if it was. The fragile paper often has more staying power than the mightiest buildings.

Here’s the URL to the old Daily Dish, starting with the final entry, in good blog fashion. The only parts of the Dish we put on dead trees: Out On a Limb: Selected Writing, 1989–2021, the VFYW photo book, and the “Cannabis Closet” series.

Another listener writes, “I just had to comment on the Laura Field episode”:

I got through almost all of it and the respectful disagreement between you two — until the part where she defends teaching The 1619 Project in schools. I understand her argument that it may not be pervasive, but I have a PhD in American history, and I respect the academic historians who have expertise in that era who bravely pointed out the narrow view of that project and its significant gaps in knowledge. What I have never understood is the Brahmin Left’s insistence that we “respect science” and expertise EXCEPT when it contradicts their own need to identify with some kind of movement. Then, they abandon this stance.

Then, they jump on the bandwagon to adopt a project that is not done by a historian, that is ideological, and that actual experts in their field (political lefties, all of them) say is short-sighted. Then why would you teach something like that? For a different “perspective”? I’m sorry, that is ludicrous. By their logic, we also need to teach Creationism alongside evolution.

If even I am tired of this BS — as a female PhD in the humanities — then I think it’s pretty obvious why Trump got a second term.

Yes, indeed. It was extremely frustrating to suddenly come across the brick wall of submission to woke pressure, after such an open discussion. I don’t think Field can really defend the 1619 Project nonsense. But to criticize it, I suspect, would be to end her academic career. Still. Even now. That’s worth noting. Wokeness still controls much of the elite. And until the elites disown it, we will have far-right governance.

On the pod with Simon Rogoff:

I was eager to hear your discussion of narcissism, as it’s said to run in my family. Like you, I can recognize some of its patterns in myself. I was curious to learn more about its fundamental nature: the line between healthy and unhealthy expression, and how to manage it in ourselves or others.

While I enjoyed learning about the childhoods of Churchill and John Lennon, I ultimately came away with more questions than answers. In your telling, narcissism seems defined by an inability to “take in” other perspectives (whether the feelings of others or objective truth), coupled with a need for performative self-aggrandizement. Rogoff suggests this stems from a childhood defined by shame and emotional neglect, where praise was reserved solely for performance. In this environment, achievement becomes the only “escape hatch” from a deep-seated sense of unworthiness.

The question I kept asking myself is: what is the healthy counterpoint to this? If someone tends towards narcissism, what course correction will lead to healthier relationships? We could imagine an opposite pathology — someone so lacking in confidence that they reflexively defer to others and denigrate themselves — but that seems equally destructive. Is this a spectrum, where there is a healthy medium between these two extremes?

Furthermore, to what extent is narcissism a prerequisite for great leadership? Are there examples of transformative leaders who displayed no narcissism but still achieved great things? If so, how did they navigate the demands of power? You categorized both Obama and Trump as narcissists, but I didn’t fully grasp the distinction that renders the trait “malignant” in one but not the other.

Finally, can narcissism be socially contagious? We live in an age of intense polarization where both sides seem increasingly non-responsive to legitimate criticism. Social media often feels like a never-ending “Battle Royale” of competitive shaming, likely a defense mechanism to protect against one's own vulnerability. This environment seems to select for leaders who are the most unyielding against these “shame bombs.” Is our current political climate a breeding ground for large-scale narcissism? If so, what is the antidote?

I wish I had the answer to all those questions. But I think we distinguished between benign and malign narcissism; and obviously social media has been a terrible influence.

This week the Narcissist-in-Chief brandished a pin of himself on his own lapel:

(Saul Loeb/AFP via Getty Images)

Here’s a guest rec for the Dishcast:

I would really like to see you bring David Pinsof onto the podcast. His blog, Everything Is Bullshit, is fantastic. I think the two of you would have similar political orientations, both being in the center, but would disagree on religion and the meaning of conservatism. It would be a fascinating episode.

First time I’ve ever heard of him, so thanks. Another rec:

You might enjoy talking to Michael Puett, a professor of Chinese history and anthropology at Harvard. His general education class on Chinese philosophy is, I believe, the third most popular course on the campus. His book is The Path: What Chinese Philosophers Can Teach Us About the Good Life, and an episode with him might pair well with your Arthur Brooks interview (which I look forward to listening to).

Sounds interesting. Next up, several readers share thoughts about the ICE killing in Minneapolis and my short piece about it, “A Totalitarian-Level Lie”:

You quoted Noem’s and Trump’s response to the shooting, but you forgot to mention the response from the unhinged mayor.

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