The Bulwark Podcast

Episode Title: Michael Weiss: Trump's Ukraine Cluster**ck
Host: Tim Miller
Guest: Michael Weiss
Date: November 25, 2025

Episode Overview

In this episode, Tim Miller is joined by Michael Weiss—a journalist with extensive expertise on Russia and Ukraine—to unpack the latest chaotic developments in the Trump administration’s handling of the Russia-Ukraine peace negotiations. The discussion covers the dysfunction and opacity behind the reported “peace deal,” the interplay of personal interests and international security, and the implications for U.S. allies and Ukraine’s future. The conversation is candid and brisk, with a strong undercurrent of concern about the state of American foreign policy and the future of liberal democracy in Europe.

Main Topics & Discussion Points

1. Trump’s Political Standing and Disarray

• [02:48] Michael Weiss: Asserts that Trump appears “very weak…vulnerable…abstracted from a lot of things you would expect the President to be well across,” and highlights unusual Republican pushback, particularly regarding U.S. policy toward Russia and Ukraine.
• Key Point: There's a shift within the GOP, with some traditional Republicans drawing the line at ceding NATO’s postwar security order or forcing territorial concessions on Ukraine.

Quote: “This is not just about one country, Ukraine, it's about NATO, it's about the European Union and it's about whether or not we have any commitment to our allies remaining."
– Michael Weiss [03:33]

2. The Epstein–Russia–Trump Back Channel Revelations

• [05:10] - [10:09] Discussion of newly revealed Epstein emails offering himself as a “back channel” between Russia, Trump, and Israel.
• Michael’s Take: Epstein was a classic global operator, using his extensive network with elites across the world, behaving “almost like his own private intel shop, in addition to being, you know, a Bond villain and a pedophile with an island.” [08:00]
• Broader Point: Such shadowy figures are common in autocratic systems, and the U.S. seems to be developing more of them under Trump’s governance.

Key Quote:
"Dictatorships tend to spawn these kinds of creatures. So unfortunately, the United States prior to becoming more authoritarian under Trump...it accelerates now. We have creatures like this…in the form of Jared Kushner and Steve Witkoff and Kirill Dmitriev.”
– Michael Weiss [09:35]

3. The Confusing “Peace Deal”– TikTok and Players Involved

• [12:09 - 29:17]

  • Trump’s ill-fated summit with Putin in Alaska yields no results. Afterwards, parallel backchannel negotiations ensue, driven by Kushner and Steve Witkoff (real estate developer with Trump connections), and Kirill Dmitriev (Russia’s sovereign wealth fund head).
  • Axios leak [18:40]: The “peace plan” is, per Michael, “28 points [that] read like Russian fan fiction…linguistically very, very Russian…they spit back and say, oh, this was written in Russian and translated to English.”

• Key Provisions in Leaked Plan:

  • No further NATO expansion, not just for Ukraine but for any country
  • Capping Ukraine’s military
  • Leveraging frozen Russian assets to “rebuilt Ukraine” but with “kickbacks” to the U.S.
  • “Weird stuff like Poland will park European jets that belong to Ukraine’s air force on their territory. So now we're telling the Poles what they're going to do.” [21:42]
  • Return of abducted Ukrainian children (an implicit admission of Russian war crimes)

Quote:
“A guy, an agent of the Russian government, hammering out a deal with not any sort of professional American diplomat, but Dim Philby, as I call him, Steve Witkoff, and Trump's very corrupt and creepy son in law, Jared Kushner. Right? So two amateurs….”
– Michael Weiss [20:41]

4. Motivations & Machinations: Who Wants This—And Why?

• [24:44]
  • J.D. Vance, Trump’s VP, eager to force the deal for political gain and to secure his succession.
  • Tension in the White House between Vance (isolationist, MAGA-aligned) and Marco Rubio (traditional internationalist).
  • Pentagon infighting, with Driscoll (Secretary of the Army, “the drone guy”) used as an unwitting messenger to Ukraine, delivering the Russian “peace” ultimatum while also learning from Ukraine’s battlefield innovations. [26:00]

Quote:
"J.D. Vance is desperate to ram this thing through. Fuck the Ukrainians. Let's give Trump a big win. He'll get his Nobel Prize, and ooh, ooh, ooh. He will anoint me the successor to Magaland and to be basically the heir apparent for 2028."
– Michael Weiss [24:51]

5. Pushback & Implosion of the “Deal”

• [29:17]
  • Deal begins to unravel as Rubio and other traditionalists (with European and Polish support) strip away the most egregious concessions.
  • New “19-point” downsized proposal emerges, removing controversial NATO and territorial concession clauses.
  • The Russians are likely to reject the watered-down deal, preferring their original maximalist demands.

Quote:
“Everybody's written out of this except this small cadre of sort of agents of not even, I mean, yes, Donald Trump, but, like, they're in it for themselves, too. They want their side action and they want to give kickbacks to the boss. So America has become...We have devolved into an authoritarian regime in this respect." – Michael Weiss [28:32]

6. Ukrainian Dynamics: Corruption, Vulnerability, and Resilience

• [33:45] - [45:21]
  • Ukraine is gripped by a serious energy corruption scandal, implicating senior officials like Rustam Umerov and Andriy Yermak.
  • Discussions around whether Zelenskyy’s vulnerability (political and military) increases odds of a “bad deal” being forced on Ukraine; risk of mass domestic backlash if he accepts.
  • Deep-rooted Ukrainian civil society and history of protest means even a weakened Zelenskyy cannot sell out the country without triggering unrest.

Quote:
"Ironically, Zelenskyy's weakness is also Ukraine's strength. Because if Zelenskyy were to sign a surrender document now, at minimum, there would be another Maidan revolution. Even in the midst of war. The people would turn out in the streets to denounce him. He would lose all legitimacy as president."
– Michael Weiss [37:04]

7. What Next? Europe’s Role and Trump's Transactional Outlook

• [38:06 - 41:32]
  • Debate over whether Zelenskyy should visit D.C.—Michael’s advice: “Stay the fuck away from Washington, D.C.”
  • Europe’s awkward position: Needing to “manage this crisis” with the U.S. while being unable to fully provide Ukraine with key military and intelligence support.
  • Trump’s transactional fixation on military equipment deals; Europeans likely to try to placate him with arms contracts.

8. Zelenskyy’s Tenacity vs. Human Limits

• [41:32 - 42:29]
  • Acknowledgment that Zelenskyy’s continued resilience is remarkable, but real concern about the accumulating weight of political, military, and social pressures on him and Ukraine.

9. Broader Stakes: Ukraine as the ‘Pepsi Challenge’ for Authoritarianism

• [42:29 - 45:21]
  • Ukraine’s survival and development as a genuine democracy, rooted in vibrant civil society, is existentially threatening for Putin’s regime.
  • Michael: “Ukraine and Russia. It's like a Pepsi challenge. If Ukraine can thrive and become a democracy with civil society the way it is, but with transparency...that is terrifying for Putin because he thinks that that might happen here, meaning in Russia."

Notable Quotes & Moments

• “These 28 points…read like Russian fan fiction.” [18:41]
• “This is kind of how the world works. You know these horrific people…worm their way into the corridors of power.” [08:00]
• “America has become...We have devolved into an authoritarian regime in this respect. It's all this sort of, you know, boyars and cronies doing the work of the czar…We are like Russia in many respects.” [28:32]
• “If Zelenskyy were to sign a surrender document now, at minimum, there would be another Maidan revolution…” [37:04]
• “He looks like your drunk uncle at Thanksgiving and sounds like it too.” (On Trump) [48:57]
• “The reason that Ukraine will survive, the reason Ukraine has survived, the reason Ukraine is a struggle worth supporting…The country has a very vibrant civil society. It has a very strong kind of democratic instinct.”
  – Michael Weiss [43:10]

Timestamps of Key Segments

• [02:48] – Trump’s political weakness and the GOP’s conflicted stance on Russia/Ukraine
• [05:10] – Jeffrey Epstein’s role as a global backchannel, implications for Trump and Russia
• [12:09] – Context for the peace deal: how negotiations unfolded, key players, and Russian objectives
• [18:41] – Anatomy of the leaked 28-point plan and why it appeared Russian-authored
• [24:51] – J.D. Vance’s ambitions and competing American interests in the negotiations
• [29:17] – Collapse of the backchannel deal as Rubio, U.S. Congress, and Europe push back
• [33:45] – Ukraine’s corruption woes and the politics of vulnerability
• [38:06] – Internal European and transatlantic tensions, and the pitfalls of a possible Zelenskyy visit to D.C.
• [41:32] – Human cost of the war for Zelenskyy and Ukrainian resilience
• [43:10] – The importance of Ukrainian civil society versus Russian authoritarian endurance

Final Takeaways

• The Trump administration’s Ukraine diplomacy is marked by chaos, incompetence, personal profiteering, and increasingly open resistance from both traditional Republicans and European allies.
• The so-called peace plan was more fantasy than statesmanship—written by Russian interests and channeled through Trump’s inner circle with little regard for Ukraine’s sovereignty or America’s alliances.
• Ukraine remains under existential threat but is also protected by its dynamic civic resilience—any “sell-out” would likely spark mass protest.
• The cycle of appeasement and pushback within the administration has become almost routine (“Palm Springs flashback / Groundhog Day”), with no real resolution in sight.
• Michael Weiss and Tim Miller both express deep skepticism about any genuine U.S.-brokered peace in the near term, but stress the importance of continued Western support for Ukrainian self-determination and democracy.

Recommended for listeners interested in:
U.S. foreign policy dysfunction, the mechanics of Trump White House decision-making, Russian influence operations, realpolitik vs. values in international relations, Ukrainian civil society, and how high-level corruption distorts geopolitical outcomes.