The Last Stand Dilemma in Ukraine

The Last Stand Dilemma in Ukraine

Author: Ryan Evans November 20, 2025 Duration: 24:59

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.


Hosted by Ryan Evans, War on the Rocks feels less like a formal briefing and more like pulling up a chair at a bar where the most consequential global issues are being debated. The conversations, often accompanied by the clink of a glass, dive into the gritty realities of security, defense, and foreign policy with the people who shape and study them. You’ll hear from a wide range of insiders and experts-from seasoned diplomats and military officers to sharp-eyed academics and journalists-who break down complex topics without the usual jargon. This podcast thrives on candid analysis and spirited discussion, exploring not just the "what" of current events, but the underlying "why" and "how" of international power dynamics. Each episode is designed to give you a deeper, more nuanced understanding of the forces shaping our world, moving beyond headlines to examine strategy, history, and the human decisions behind the news. It’s the original series from the platform, offering listeners a direct line to thoughtful, often provocative, perspectives that are usually reserved for closed-door meetings. Tuning in provides a consistently engaging and informative look at the challenges and intrigues defining global affairs today.
Author: Language: English Episodes: 100

War on the Rocks
Podcast Episodes
The Actively Retired Polish General Building a Strategic Culture [not-audio_url] [/not-audio_url]

Duration: 35:39
Last year, Rajmund Andrzejczak retired as Poland's chief of the general staff, but he has been busy since. During a recent visit to Washington, he spoke with Ryan about his career, European security, Polish defense, manp…
Is Russia's Window for Gains this Summer Narrowing? [not-audio_url] [/not-audio_url]

Duration: 23:47
Michael Kofman dropped into WOTR HQ to chat with Ryan about the war in Ukraine. From Russia's culminated offensive on Kharkiv, to battlefields of the Donbas, to ongoing fighting in the south, to Russia's displaced Black…
A Conversation with Secretary of the Air Force Frank Kendall [not-audio_url] [/not-audio_url]

Duration: 35:13
Secretary of the Air Force Frank Kendall was kind enough to spend some time with Ryan talking about the reorganization of the Department of the Air Force and modernization. They also discussed the challenges new entrants…
What Will Ukraine Do To Stay in the Fight this Year? [not-audio_url] [/not-audio_url]

Duration: 18:02
The U.S. Congress finally passed the security supplement, authorizing a large amount of funding and support to keep Ukraine in the fight. This package buys Ukraine another year of time. What will Ukraine do with that tim…
Ukraine and a Fractured World [not-audio_url] [/not-audio_url]

Duration: 41:47
Ryan sat down with three friends to talk about the war in Ukraine through the lens of a new edited volume on the topic. Enjoy this conversation with Andrea Kendall-Taylor (former CIA), Hal Brands, and Alexander Bick (for…
Crossing the Threshold [not-audio_url] [/not-audio_url]

Duration: 35:53
Nick sat down with Eric Brewer, Dana Stroul, and Gavin Clough to discuss how the conventional, proxy, and nuclear threats Iran poses are evolving. Who was deterred and who wasn't by the latest Iranian and Israeli strikes…
Spacepower and the Private Sector [not-audio_url] [/not-audio_url]

Duration: 20:05
On the sidelines of the National Space Symposium, we threw a little party and recorded a podcast, because why not? Our special guest was Assistant Secretary of Defense for Space Policy John Plumb and the main focus of th…