The Last Stand Dilemma in Ukraine
War on the Rocks
War on the Rocks
4.6 • 1.1K Ratings
🗓️ 20 November 2025
⏱️ 25 minutes
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Summary
When should Ukraine commit more forces to a perhaps desperate stand to hold ground it will likely lose? And when is it the difficult but correct choice to preserve the force and pull back to the next defensive line? This is the real, agonizing strategic dilemma shaping the war, now highlighted in the fight for Pokrovsk.
Distinguished strategist Lawrence Freedman joins Ryan at a cafe in Vilnius, where they were both speaking at a conference, to dissect this critical question. They also sort through how this relates to each side's theory of victory and the shifting realities of the battlefield.
Transcript
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| 0:00.0 | You are listening to the War on the Rocks podcast on Strategy, Defense, and Foreign Affairs. |
| 0:13.8 | My name is Ryan Evans. I'm the founder of Warren the Rocks. |
| 0:16.5 | While I was in Vilnius at the defending the Baltics Conference, I hung out with my good friend, |
| 0:20.7 | Lawrence Friedman, and we had a short conversation about the strategy in the war in Ukraine, |
| 0:25.0 | both from the Russian and Ukrainian sides, and in particular focused on what I like to call |
| 0:29.6 | the last stay-in problem, which is, when should Ukraine decide to give up territory that it's |
| 0:34.9 | slowly losing, and when should it stay and fight as much as possible. |
| 0:38.8 | It's more of a dilemma as we discuss and Lori has this great post on his substack, |
| 0:44.3 | which is called Comment is Freed. And if you don't subscribe to it, frankly you're a fool. |
| 0:48.7 | So you should go subscribe to it right now and enjoy the conversation. |
| 0:52.4 | Great to have you on the show again, my friend. |
| 0:54.9 | Good to be with you. |
| 0:59.8 | So you're working on another important piece of writing, and we touched on it yesterday in conversation here in Vilnius about this dilemma and problem, I think, in Ukrainian strategy of |
| 1:05.2 | making last stands and perhaps the wrong places or perhaps not. You know, Bachmoud is one, |
| 1:10.3 | probably the biggest example |
| 1:11.3 | on what we're seeing in Proofs might prove to be the other. |
| 1:14.0 | And we'd just like to get your thoughts or how you think about this. |
| 1:16.9 | So I think the first thing is to accept it as a dilemma. |
| 1:20.6 | It's not straightforward. |
| 1:22.2 | One of the reasons it's not straightforward is when you're looking at what is effectively |
| 1:27.2 | a retreat, to have an orderly retreat, |
| 1:30.3 | actually you need time, you need to take the decision in a timely way, and when it's possible to move |
... |
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