Podcast Summary: To The Contrary with Charlie Sykes

Episode: Nicholas Grossman: UN Escalators, NATO, and Free Speech
Date: September 28, 2025
Host: Charlie Sykes
Guest: Nicholas Grossman (international relations professor, national security expert)

Overview

The episode explores a tumultuous week in American and international politics, unpacking a series of chaotic events ranging from Donald Trump’s erratic United Nations appearance and shifting stance on Ukraine, to a politicized military meeting called by Pete Hegseth, the attempted canceling and subsequent reinstatement of Jimmy Kimmel, and the extraordinary indictment of former FBI director James Comey. Sykes and Grossman reflect on the implications for national security, the rule of law, free speech, democratic norms, and the increased perception of fragility in American institutions.

Key Discussion Points & Insights

1. A Week of Political Pandemonium

[01:23-04:40]

• Sykes opens by listing chaotic, unprecedented events—Trump’s all-caps Tylenol rant, an embarrassing UN performance, bizarre focus on escalators, Jimmy Kimmel’s temporary firing, a shooting at an ICE facility, Hegseth’s summoning of generals, and mounting government shutdown fears.
• "It did feel as if something shifted. Now, whether it shifted in a positive direction or a negative direction, we're going to try to hash out.” (Sykes, [01:29])

2. Hegseth’s Call to Generals: Politicizing the Military

[04:40-08:15]

• Grossman flags Hegseth’s in-person recall of 800 generals and admirals as unprecedented and concerning for national security—costly, logistically difficult, and risky to readiness.
• "There's no reason to take, say, an admiral off an aircraft carrier in the Pacific near China and make him fly all the way back to Virginia to have some sort of meeting in person." (Grossman, [05:45])
• Raises fears the meeting could be a loyalty test for the generals: “Who’s willing to raise their hand and say they will obey any order that Donald Trump gives?" (Sykes, [06:27])
• Grossman critiques the systematic politicization of the military, referencing removal of trans and Black leaders, and compares U.S. stability to nations like Pakistan, where military politicization has led to lasting damage.

3. Trump’s UN Speech: A Global Embarrassment

[08:15-11:13]

• Trump’s speech is described as “meandering, demented, deranged,” with foreign delegates stunned by his rants (Sykes, [08:15]).
• Grossman argues American media normalizes Trump, but the world sees “at absolute best... incompetent, possibly insane leadership.”
• “This was Trump essentially giving the world a giant middle finger.” (Grossman, [09:52])
• The world now views the US as unreliable, especially if it re-elects Trump: “Once everybody thinks the United States is not coming, then NATO is effectively dead.” (Grossman, [14:22])

4. Flip-Flopping on Ukraine & NATO Credibility

[11:13-15:28]

• Trump reversed course, briefly supporting Ukraine. Grossman dismisses this as unreliable theater, warning it undermines NATO deterrence.
• Grossman highlights worrying “It depends” answers on defending NATO allies: “That exact attitude undermines the confidence in NATO’s deterrent.” (Grossman, [13:16])
• Sykes imagines Trump refusing to defend Eastern Europe: “I could certainly imagine him taking some action against Estonia and Donald Trump coming out and saying, you know, protecting Vilnius is not worth a single American life.” ([15:08])
• The consensus: Trump's ambiguity emboldens adversaries like Putin.

5. The Jimmy Kimmel Saga & Free Speech

[18:15-24:47]

• Kimmel’s firing after a mild joke at Trump’s expense, under pressure from the FCC and with Disney/Sinclair caving, sparked backlash and was soon reversed.
• Grossman draws historical parallels: “People thought of analogies of Joseph Goebbels and the Nazis kicking comedians off the air because they made fun of Hitler.” (Grossman, [20:32])
• A rare cross-ideological defense of Kimmel, with even Cruz, Shapiro, McConnell speaking out.
• Corporate response: Disney and partners “very quickly bow[ed] down” but faced a strong civil backlash—consumer boycotts, threats from creative talent (e.g., Pedro Pascal), and “Disney adults” canceling expensive events ([21:25]-[22:08]).
• Grossman: “The Nazis could get the comedians off the air. ... Trump couldn’t get one comedian that makes fun of him off television—[he] is quite limited in his authoritarian abilities.” ([24:16])
• Sykes: “We are not alone. ... His power relies on people thinking he’s powerful, but also that the opposition feels that they’re weak and that opposition is pointless.” ([24:47])

Notable Quote

• Jimmy Kimmel (paraphrased by Sykes): “This show is not important. What’s important is that we live in a country that can have a show like this.” ([25:53])

6. The Comey Indictment: Crossing the Red Line

[24:47-34:48]

• The indictment of former FBI director James Comey is described as an “extraordinary, naked” act of political vengeance—Trump fired the U.S. Attorney who refused to indict, installed a loyalist, and 48 hours later, secured an indictment.
• Sykes: “It just feels as if it's naked. And that any pretense [of] DOJ independence is not eroded, it's been destroyed.” ([29:28])
• Grossman: “It's a dominance display. ... It's obviously false, I'm lying, you know I'm lying, I know you know I'm lying—and guess what? I'm doing it anyway. And you can't do anything about it.” ([30:22])
• Grossman contends the justice system, while battered, is not fully subverted: charges are weak, Comey likely prevails, but the harassment serves as warning to others.
• Comparison to Putin: “Putin waited years and got everything in place before he made this sort of move. ... Trump and MAGA are jumping right into it very quickly.” ([34:27])
• Both worry about normalization—as retributions continue, will each new outrage shock less?

7. Gutting of the DOJ & State Capacity

[37:46-42:32]

• Grossman notes the institutional collapse as career prosecutors are purged and replaced by loyalists, drawing on Hannah Arendt’s studies of totalitarian transitions.
• Many legal professionals have resigned rather than cooperate, but others remain—potentially ready to resist further illegality.
• Sykes: “Maybe at some point you’re going to have to see the kind of collective action in the legal community that we just saw in the entertainment community.” ([42:32])

8. Looming Government Shutdown

[44:25-49:47]

• Both see shutdown politics stuck in an obsolete playbook; Sykes and Grossman argue Democrats can neither cave nor expect to be blamed, as Trump flouts Congressional authority and has already sacked thousands of federal workers.
• Shutdowns now entail real and lasting reductions in state capacity, with “downstream effects for Social Security ... Fema ... [and] government breakdowns.” ([49:47])
• On “America First” contradictions: U.S. prepared to bail out Argentina while slashing domestic services—a ripe target for political messaging.

9. Rise of an International Authoritarian Network

[51:56-54:59]

• Grossman: “Some sort of like a fascist international ...a kind of global struggle against liberalism, the left, openness, wokeness, pluralism… Putin in Russia, Orban in Hungary, Argentina… they see as ‘us’ these other kind of corrupt far right ... leaders.” ([54:14])

Notable Quotes & Moments (with Timestamps)

• On the Military Recall
  “There's no reason to take, say, an admiral off an aircraft carrier in the Pacific near China and make him fly all the way back to Virginia to have some sort of meeting in person.” —Nicholas Grossman ([05:45])
• On Trump’s UN Speech
  “This was Trump essentially giving the world a giant middle finger.” —Nicholas Grossman ([09:52])
• On NATO Deterrence
  “Once everybody thinks the United States is not coming, then NATO is effectively dead.” —Nicholas Grossman ([14:22])
• On Authoritarian Overreach
  “It's a dominance display. ...I'm lying, you know I'm lying, I know you know I'm lying—and guess what? I'm doing it anyway.” —Nicholas Grossman ([30:22])
• On Free Speech Backlash
  “The Nazis could get the comedians off the air. ...the idea that Trump couldn't get one comedian that makes fun of him off television is quite limited in his authoritarian abilities.” —Nicholas Grossman ([24:16])
• On Kimmel’s Return
  “This show is not important. What's important is that we live in a country that can have a show like this.” —Jimmy Kimmel (quoted by Sykes, [25:53])

Important Segment Timestamps

• [01:23] Chaos of the week—Sykes intro
• [04:40] Hegseth’s military meeting—Grossman raises alarm
• [08:15] Trump’s UN speech and global perception
• [11:13] Ukraine policy reversal and NATO doubts
• [18:22] Jimmy Kimmel firing/free speech episode
• [24:47] Kimmel returns; limits of Trump’s power
• [29:28] Comey indictment—definition of red line crossed
• [30:22] Grossman’s “dominance display” theory
• [34:48] Authoritarian overreach and American normalization
• [44:25] Government shutdown politics
• [49:47] Effects of administrative purges
• [54:14] Rise of “fascist international”

Conclusion

The episode paints a vivid picture of accelerating democratic backsliding and authoritarian overreach in the United States, but also highlights moments of civil resistance, the limits of Trumpist power, and the continuing importance of collective action against normalization and cynicism. Sykes closes by emphasizing the need for ongoing conversation and vigilance:
“It becomes more obvious every day that we have to continue having these conversations to remind ourselves we are not the crazy ones.” ([56:36])