The Bulwark Podcast — August 27, 2025

Guest: Jake Sullivan (Former Biden National Security Advisor)

Host: Tim Miller

Episode Overview

In this incisive episode, Tim Miller welcomes Jake Sullivan, former National Security Advisor to Joe Biden, for a wide-ranging, candid, and energetic discussion of the Trump administration's foreign and domestic policy, U.S. standing in the world, the future of American democracy, lessons from the Ukraine and Israel crises, Democratic Party strategy, Biden’s debate debacle, and some lighter moments to close.

Sullivan offers detailed, firsthand insights into the stakes of Trump’s second term, its alarming pace toward autocracy, the administration’s about-faces on China and Russia, American security blind spots, and the evolving Democratic response. The episode’s tone is sharp-eyed, sometimes grim, but leavened by sarcasm, stories, and some well-placed zingers.

Key Discussion Points & Insights

Trump’s Autocracy Playbook & The State of U.S. Democracy

• Mutual disbelief at recent Cabinet meeting “praise-fests” for Trump
  • "[Cabinet members] played the part of a Kim Jong Un documentary, we've just run out of praise for Donald Trump. It's all been done, it's all been given." — Jake Sullivan (01:43)
• Sullivan on the depth of danger:
  • Trump’s open attacks on media, law firms, universities, and civil society mirror Erdogan and Orban, but "at breakneck speed." The redistricting push and a string of guardrail-smashing actions amount to "a very concerted effort" out of the autocrat’s playbook. (03:10–04:32)
  • Notably, the attack on law firms is “deeply structural,” signaling a system-wide effort across American institutions (04:47).

Dismantling Expertise in Government

• Purge of career officials in DOD, intelligence, and cyber:
  • Sullivan mourns the loss of "some of the most incredible lifelong non-political public servants," especially in cyber at NSA, raising a red flag about a “massive gap in America’s cyber capabilities right now at exactly the wrong moment.” (06:33–08:25)
  • “Anybody who basically tells the truth, who doesn't put spin on the ball...they get shown the door. That is Xi Jinping stuff, in my view.” — Jake Sullivan (07:06)

China Policy U-Turns: “Trump Is Making China Great Again”

• Trump’s inconsistent and transactional approach:
  • In trade and AI, Trump’s public tough talk masks private backtracking:
    • "Taco Trump always chickens out" in trade wars—big tariffs, but he folds under pressure, giving China confidence to push the U.S. around. (10:13)
    • Trump ignored previous blockades on high-end AI chips to China after meeting with Nvidia’s CEO—“He let somebody who had a financial interest in selling these chips to China convince him to do it.” (11:21)
  • “If you’re a leader in China right now, you’re watching the United States basically become less appealing as a place for talent to come, cut down on its own research, start trade wars with its allies—all things that are core to America—totally gutter. And then sell us these chips.” — Jake Sullivan (12:43)
• Failures with TikTok and Chinese investments:
  • Trump's refusal to enforce the TikTok divestiture law "is very much about personal and political gain." (11:43)
• Allies' dismay:
  • America’s unpredictability pushes allies toward China: "What they're talking about is de-risking from the United States. They now see the US as the big disruptor." — Jake Sullivan (15:35)
  • China now polls ahead of the U.S. in popularity in many countries (16:25).

Notable Quotes

• "President Trump is just doing [China’s] work for them. All we have to do is sit back and watch." — Jake Sullivan, quoting a Chinese official (12:54)
• "China is sitting pretty comfortably right now, feeling like they're in a good position. That was not the case a year ago.” (13:06–13:32)

American Global Standing & Relations with Allies

• Europe and Asia de-risking from the U.S. (15:35)
  • "The US Brand is in the toilet and China is looking like, actually, in a bizarre way, a more responsible player."
  • Former partners (like India) are now hedging toward China due to Trump’s trade offensives.

Russia, Ukraine, and the Red Carpet Blunder

• The Putin Summit, Red Carpet, and Optics Disaster:
  • Discussion of the unusual display of U.S. soldiers on their knees rolling out the red carpet for Putin on a military base—a move Sullivan attributes to “not thinking it through” and decries the terrible optics: "That image sent shockwaves through our allies, through the Ukrainians, and frankly sent a message to Putin, 'Hey, I'm in the capride seat here.'" (21:13)
• Putin extracting wins:
  • "No Ceasefire, no consequences. I'd call that a pretty big win for [Putin] out of Alaska." (22:13)
• Trump’s refusal to squeeze Russia economically:
  • Sullivan says the Biden administration ramped up oil sanctions, the “big lever” the U.S. holds, but Trump refuses to use it—thus offering Putin a freer hand (23:00–24:11).

Notable Quotes

• "We weren't going to negotiate over the head of Ukraine." (22:35)
• On the summit: "You rarely see [that] from an American president." (20:33)

U.S. Military Aid to Ukraine: Lessons and Critiques

• Why some weapon systems weren’t provided earlier:
  • On F-16s, Abrams tanks, and ATACMS: logistical, not just political challenges. Emphasizes the massive, baseline military aid provided, not just the timing of specific systems (26:57–32:27).
  • “The idea that if we had given F-16s a few months earlier would have dramatically changed the world—I think that is not serious.” (27:56)
• Why not direct U.S. military engagement?
  • Sullivan strongly defends choice not to provide direct air support: "That would have been the United States directly at war with Russia...I also think if we were going to enter the war directly, you'd want to go to Congress." (28:17)
• Evolution of the war:
  • It's “now more of a drone war than a tank or infantry war.” (31:03)

Notable Quotes

• “[Some colleagues] have already pocketed the baseline, which is just a massive amount of military aid, intelligence support, deep integration...That was not a foregone conclusion.” (26:57–27:12)

Volodymyr Zelenskyy: Leadership Profile & Trump-Era Oval Office Debacle

• Sullivan on Zelenskyy’s transformation:
  • “In the first 24 hours, he came into his own. You could almost see a physical change in Zelensky from seeing him in 21 to after Feb ‘22 … He really ended up inhabiting the fighting spirit of the nation.” (33:15)
• On Trump and Vance’s treatment of Zelenskyy:
  • “He was kind of floored and dumbfounded by it. Rightly so, because it's flooring and dumbfounding.” (35:53)
  • Tim Miller: "A little too nice to JD to call him a hammer. I don't know, just condescending prick dropped on him." (36:03)

Israel, Gaza, and Sullivan’s Reflections

The October 7th Jinx Memoir

• Tim jibes Sullivan about his now-infamous “The Middle East is quieter today than it has been in two decades” quote eight days before Hamas's attack:
  • "I'm a superstitious person...never say possibly you're cursed." (36:44)
  • Sullivan: “Obviously I wouldn't say it again.” (37:46)

U.S. Policy During the Gaza War—Retrospective

• Biggest regret:
  • “My top regret is just the immense human tragedy...the death, the destruction, and it just going on and on. That's hard to sit with.” (38:38)
• On pressuring Israel:
  • Sullivan is open to the idea that more public pressure could’ve been used, but doubts it would have fundamentally changed outcomes: “Was there not a way to be more public about your critiques and pressure him more from a public standpoint? ...I'm open to that argument.” (43:00)
  • However, he insists U.S. efforts kept famine at bay during Biden’s tenure: "We pressured Israel in ways that opened crossings and moved trucks to the point where I believe that we did prevent the famine that was warmed up last year." (44:19–44:41)
• On the policy shift today:
  • “The case for withholding weapons from Israel today is much stronger than it was one year ago...It’s just bombing rubble into rubble.” (46:36)

Notable Quotes

• "People who thought this was wrong from the start didn't stare squarely in October 7th, and people who think it's just and righteous today are not staring squarely at what is happening in Gaza right now." (41:40)
• "A vote to withhold weapons from Israel is a totally credible position." (47:21)

On U.S.–Israel Relationship Future

• The future hinges on the direction of Israeli politics and democracy:
  • "If nothing changes in their government...it won't be the Israel as we've known it. And I think a lot of Israelis would say...they wouldn't recognize Israel then." (48:24)

Biden’s Debate Debacle

• Sullivan professes genuine shock at Biden’s disastrous debate performance:
  • "The Joe Biden I dealt with every day in the Oval Office, in the situation room, was someone who was well and faithfully executing the duties of his office. I did not expect by any stretch of imagination a performance like that at the debate." (51:33)
  • Tim Miller pushes back, expressing incredulity that insiders weren’t more concerned—Sullivan: “I expected Joe Biden to go and turn in at least an okay performance in the debate. That's what I expected. And he very much did not do that.” (53:09)
  • Sullivan maintains: “Did I have concerns about him doing the job as president? ...I did not have concerns.” (55:10)

Quick Hits, Odds & Ends

• Havana Syndrome controversy:
  • Sullivan says the administration put “a huge amount of effort” into getting to the bottom of it, ultimately finds “no foreign nexus,” but insists “we shouldn’t shut the book on it.” (56:24–57:07)
• The Pop Quiz (for NSC alums, foreign leaders edition):
  • Successfully names Ramzan Kadyrov as Chechnya’s head, Anwar Ibrahim (Malaysia), partial credit for Estonia—beats Tommy Vitor, ties with Ben Rhodes (57:28–58:57).

Notable Quotes & Memorable Moments (with Timestamps)

• “Trump’s effort, basically, to coerce and silence the media... looks a lot like Erdogan...like Orban in Hungary, but...at breakneck speed.” — Sullivan (03:10)
• “Anybody who basically tells the truth...they get shown the door. That is Xi Jinping stuff.” — Sullivan (07:06)
• “Taco Trump always chickens out... it's particularly apt when it comes to him launching a trade war against China and then turning around and backing down. China made him fold.” — Sullivan (10:13)
• “President Trump is just doing [China’s] work for them. All we have to do is sit back and watch.” — Sullivan (12:54)
• "The US Brand is in the toilet and China is looking like, actually, in a bizarre way, a more responsible player." — Sullivan (16:25)
• “That image...sent shockwaves through our allies, sent shockwaves through the Ukrainians, and frankly sent a message to Putin, hey, actually I'm in the capride seat here.” — Sullivan (21:13)
• “In the first 24 hours, [Zelenskyy] came into his own...He really kind of ended up inhabiting the fighting spirit of the nation.” — Sullivan (33:15)
• “People who thought this was wrong from the start didn't stare squarely in October 7th, and people who think it's just and righteous today are not staring squarely at what is happening in Gaza right now.” — Sullivan (41:40)
• "The Joe Biden I dealt with every day...was making decisions, involved in crisis management, and I did not expect by any stretch of the imagination a performance like that at the debate." — Sullivan (51:33)

Timestamps for Important Segments

• Autocracy, law firm purges, and cabinet slavishness: 01:43–05:48
• Cyber, DOD, intelligence agency purges: 06:33–08:25
• China, AI chips, TikTok, policy reversals: 09:20–14:01
• Allies' shift toward China: 15:09–17:12
• Russia/Ukraine, Putin Summit, red carpet optics: 18:53–22:17
• Sanctions, U.S. leverage over Russia: 22:17–24:11
• Weapons systems for Ukraine—F-16s, Abrams, ATACMS: 26:57–32:27
• Zelenskyy’s transformation: 33:00–34:41
• Oval Office debacle for Ukraine/Trump/Vance: 35:38–36:08
• Israel-Gaza, policy regrets, famine aid: 36:44–45:55
• U.S.-Israel relationship and Democratic evolution: 45:55–48:36
• Biden debate shock & reflections: 50:30–55:13
• Havana Syndrome: 56:24–57:28
• Pop Quiz & closing: 57:28–59:24

Tone & Style

The conversation is fast-moving, sharp, and peppered with irreverence, but always anchored by substance and concern for democratic norms. Sullivan moves comfortably between damning specific betrayals, policy nuance, and honest reflection. The chemistry with Miller adds levity—whether in their Minnesota references (“Zelenskyy a little more Arnold than Jesse [Ventura],” 33:33) or banter about the now-mythic “jinx” op-ed and podcast pop quizzes.

For Further Listening

This episode is essential for those wanting an insider’s perspective on the Trump administration’s threat to democratic norms, the shifting tectonics of American power abroad, and frank after-action reflections from Biden’s top national security hand. Strongly recommended for politically engaged listeners anywhere along the spectrum.