The Lawfare Podcast: Tomahawks, Trump, and Armed Neutrality for Ukraine
Date: October 21, 2025
Host: Anastasia Lopatyna (Lawfare Institute, Ukraine Fellow)
Guests:
- Eric Chermela (Carnegie Endowment for International Peace, Senior Fellow)
- Mykhailo Soldatenko (Scholar of International Law, Doctoral Candidate at Harvard Law School)
Episode Overview
This episode delves into the current state of U.S.-Ukraine relations after the pivotal White House meeting between President Trump and Ukrainian President Zelensky. The discussion unpacks the implications of supplying Ukraine with Tomahawk missiles, the concept of "armed neutrality" for Ukraine, the latest contours of Russian demands, the complexities of shuttle diplomacy and its risks, and the persistent obstacles to peace. The guests offer insights into Kyiv's negotiating strategy, the nuanced role of neutrality in potential settlement frameworks, and the challenges of forging a durable security arrangement for Ukraine.
Key Topics and Insights
1. The Trump-Zelensky White House Meeting and the Tomahawk Missile Debate
[02:14–05:56]
- Background: On October 17th, Zelensky met Trump at the White House for their sixth post-reelection encounter, with a primary aim: persuading the U.S. to supply Tomahawk missiles for Ukraine’s deep-strike campaign against Russia.
- Historical Context: The Biden administration refused this request in 2024, citing concerns about missile stockpiles, costs, Ukraine’s own advances with drone systems, and escalation risks.
- Shift Under Trump: Initial hints from Trump and VP J.D. Vance suggested newly positive consideration, possibly as leverage against Russia amid negotiation stalemates.
- Outcome: The meeting was described as emotional and unproductive; Trump ultimately refused to supply Tomahawks and reverted to general calls for a negotiated settlement.
Notable Quote:
"Enabling Ukraine with American made missiles to strike deep inside Russia is still the consideration that any president has to think about."
— Eric Chermela [04:13]
2. Trump’s Diplomatic Approach: Shuttle Diplomacy or Performative Pivot?
[07:29–13:52]
- Analysis of Trump’s Rhetoric: Trump’s policy positions appear mercurial, oscillating between pro-Ukraine and pro-Russia statements, forcing both sides to adapt continually to shifting signals.
- Nature of Diplomacy: Mykhailo describes this as an improvised version of "shuttle diplomacy," where Trump positions himself as mediator but frequently shifts alliances.
- Implications for Kyiv: Unpredictability adds risk for Ukraine, complicating planning and expectations.
Notable Quotes:
"This is a sort of shuttle diplomacy in a way. And I think especially Ukrainians need to be clear, that if after this meeting there would be another turn, there are always risks..."
— Mykhailo Soldatenko [08:43]
"He can say one thing one day and then say the complete opposite the next day. And there's absolutely no political ramification for him whatsoever."
— Eric Chermela [12:51]
3. The Trump-Putin Call and What Russia Wants from Negotiations
[15:17–21:58]
- Influence of Trump-Putin Call: An unannounced call between Trump and Putin, just before the Zelensky meeting, seemingly shifted Trump's stance, particularly against giving Tomahawks to Ukraine.
- Russia’s Demands: Russia's main condition remains Ukraine’s withdrawal from the rest of Donetsk Oblast (Donbas), while expressing some flexibility on Zaporizhzhia and Kherson.
- Constitutional Claims: Russia’s formal claims on five Ukrainian regions, including those it doesn’t fully control, frame its negotiating leverage.
Notable Quote:
"There has been way too much credulous, you know, belief that the Russians are just ready to make a deal and Putin wants to end the war... That is not a smart way to go about this."
— Eric Chermela [18:58]
4. Territory, Ceasefires, and the "Freeze the Front Line" Proposal
[25:33–29:26]
- White House Meeting Recap: Despite prolonged and heated dialogue, Trump’s post-meeting statement advocated for a ceasefire at current frontlines ("Let both claim victory, let history decide"), reverting to rhetoric from earlier in the year.
- Analysis of Offer: Uncertain whether Trump's position is reliable, as previous apparent commitments have been quickly reversed.
- Russian Position: Russians remain adamant about taking the rest of Donbas and seem uninterested in true neutrality or Western-style security guarantees for Ukraine.
Notable Quote:
"Freezing on the front line... if that is Trump's true position and he's going to stick with it, it is significant because it's the only area where he seems to be pushing back in a consistent manner against Russian demands."
— Eric Chermela [26:43]
5. "Armed Neutrality" for Ukraine: Concept and Feasibility
[33:00–42:39]
- Definition and Background: "Armed neutrality" means Ukraine would maintain strong self-defense capabilities without joining military alliances like NATO.
- Past Negotiations: In 2022, when Ukraine floated neutrality in Istanbul talks, Russian territorial demands seemed less maximalist, suggesting a potential opening.
- Kremlin Perspectives: Russians seek demilitarization and severance of Ukraine from Western military support — their interpretation of "neutrality" is substantially different from the Western or Ukrainian expert vision.
Notable Quotes:
"If you present a robust security arrangement... then you have a kind of a good case to present it to the Ukrainian population as a substitute to NATO."
— Mykhailo Soldatenko [44:04]
"The visions of neutrality and non alignment to date at least have been completely non overlapping."
— Eric Chermela [39:22]
6. Security Guarantees and Western Support: Limits and Red Lines
[47:01–53:36]
- Security Guarantees: True Article 5-type commitments from the U.S. or Europe are unlikely; realistic goals might be long-term military aid, training, and equipment.
- Risks of Weak Deterrence: Western support without "boots on the ground" may not be enough to deter future Russian aggression, given Russia’s demonstrated willingness to endure costs.
- Possible Compromises: Some experts argue for a U.S. executive order (like the "Qatar model") as a flexible, if ambiguous, guarantee — but Trump would be unlikely to interpret this as a promise to commit U.S. troops.
Notable Quotes:
"Ukraine has to operate with the understanding that it's not going to get a clear security guarantee to come to its assistance."
— Eric Chermela [48:42]
"When you introduce a possibility of the US armed force, at least in a limited way... I think that would be completely another analysis and calculus from their side because that would mean for them... a risk of war with the United States for them may be existential..."
— Mykhailo Soldatenko [53:36]
7. Public Opinion and Political Taboo Around Neutrality in Ukraine
[42:39–60:32]
- Ukrainian Sentiments: Neutrality is largely equated with capitulation and defeat, both among elites and the broader population.
- Potential for Debate: Mykhailo argues that armed neutrality could be reframed as a robust, sovereign security policy — but this requires careful, transparent public debate and international support.
- Broader Russian Goals: Even an agreement on neutrality and territorial issues may not address Moscow’s ambitions to influence Ukraine’s language, culture, and internal politics.
Notable Quotes:
"In the public sphere, especially in Ukraine, neutrality was presented as equal to capitulation and as equal to the reduction of armed forces. So when you speak with people, they immediately jump into the conclusion that this is some sort of a weak state without arms, which is not correct."
— Mykhailo Soldatenko [43:39]
"When you dig down into these, these polls and you ask Ukrainians about their kind of future visions, it does seem like they would actually accept some form of this, this [armed non alignment]."
— Eric Chermela [61:05]
Notable Quotes & Moments (with Timestamps)
-
On U.S. Leverage in Negotiations:
"He’s not willing to deploy any of the leverage that the United States actually has... he seems a little bit more comfortable using the leverage against Ukraine, which is withholding or in some cases suspending assistance."
— Eric Chermela [11:34] -
On Russian Constitutional Claims:
"By making this concession, Putin acknowledged... your constitution is not a red line anymore."
— Mykhailo Soldatenko [20:06] -
On the Limits of Western Security Guarantees:
"As much as I would want one, I don't see the ingredients at this point for a full-blown security guarantee from the United States or European countries..."
— Eric Chermela [47:35] -
On the Realism of Exhausting Diplomacy:
"This is challenging. It's not guaranteed that that will work out, but that would at least show that we exhausted diplomacy and we did everything possible from our side before continuing the war of attrition."
— Mykhailo Soldatenko [59:51]
Segment Timestamps
- [02:14] – Introduction to the Tomahawk debate & White House meeting
- [07:29] – Assessing Trump’s rhetorical swings and mediation tactics
- [15:17] – Impact of the Trump-Putin call and new Russian demands
- [25:33] – Ceasefire negotiations, territorial lines, “freeze the front” concept
- [33:00] – Armed neutrality as an untested negotiating option
- [47:01] – Security guarantees: realistic expectations and deterrence
- [53:36] – Can neutrality plus robust defense deter Russia?
- [59:51] – Ukrainian skepticism, need for exhausting diplomacy
- [61:05] – Public opinion and potential for reframing neutrality
Conclusion
This episode provides a rich, multidimensional examination of the diplomatic impasse over Ukraine. The hosts and guests lay bare the dissonance between public expectations, political rhetoric, and the gritty realities of negotiation with Russia, emphasizing the need for Ukraine and its allies to clarify their own vision and red lines before entering further talks. The prospects of "armed neutrality" are discussed as both a possible avenue and a massive political lift — one that demands new thinking, broader public debate, and genuine alignment among Kyiv, Washington, and Brussels.
For listeners seeking a nuanced understanding of current Ukraine diplomacy, alliance politics, and the limitations of quick fixes, this conversation is essential.