Giles Milton - Churchill’s Unholy Alliance and Why It Changed Everything
The Winston Marshall Show
Winston Marshall
4.8 • 657 Ratings
🗓️ 27 December 2025
⏱️ 69 minutes
🧾️ Download transcript
Summary
In this episode of The Winston Marshall Show, I sit down with historian and bestselling author Giles Milton for a deep historical conversation about the Second World War, the alliance with Stalin, and the decisions that shaped the post-war world.
We explore how Winston Churchill came to ally with Joseph Stalin after Hitler’s invasion of the Soviet Union, despite viewing communism as a murderous and authoritarian system. Giles explains the extraordinary political reversal of 1941, the moral compromises involved, and why Churchill saw the alliance as a necessary pact with the devil.
The discussion moves through the Nazi-Soviet Pact, Lend-Lease, the meetings at Tehran, Yalta, and Potsdam, and the immense role American industrial power played in defeating Hitler. We examine how Stalin manipulated his allies, outmanoeuvred Roosevelt, and secured control of Eastern Europe, laying the foundations for the Cold War.
We also discuss the betrayal of Poland, the division of Germany, the origins of the Iron Curtain, and Churchill’s secret plans to confront the Soviet Union after the war, revealing how fragile the wartime alliance truly was.
A fascinating conversation about power, war, pragmatism, and how the alliance that defeated Nazism reshaped the world that followed.
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Chapters
00:00 Introduction of Giles Milton and The Stalin Affair
04:50 Churchill's Anti-Communist Stance and Political U-Turn
10:46 The Lend-Lease Program and American Aid
22:28 Stalin's Tactics and the Winter Turning Point
26:54 The Tehran Conference and Churchill's Meeting with Stalin
33:34 The Yalta Conference and Post-War Planning
53:43 The Potsdam Conference and the Cold War
59:48 Churchill's Iron Curtain Speech and the End of the Alliance
1:03:45 Operation Unthinkable and Churchill's Final Strategy
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Transcript
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| 0:00.0 | Hello and welcome to The Winston Marshall Show with me, Winston Marshall. |
| 0:14.7 | I sat down with the British historian, Charles Milton, to explore his latest book, The Stalin Affair, the story of Joseph Stalin |
| 0:24.5 | and his relationship with Churchill, Roosevelt, and the West in their quest to defeat Nazism |
| 0:31.7 | and Hitler. But in that quest, did the Western allies align themselves with a devil? |
| 0:39.8 | We looked at the character of Stalin. |
| 0:41.7 | We looked at the various meetings between Stalin and Churchill and those Western leaders. |
| 0:49.9 | All of this are much more. |
| 0:51.4 | Before you hear from Charles, I wanted to say thank you. Thank you for your |
| 0:56.0 | continued support. Remember to press, follow and subscribe wherever you get your podcast from. |
| 1:01.3 | And if you head over to winstonmartial.com.ukuk, you'll enjoy an extended conversation |
| 1:06.3 | where Charles and I discuss another one of his books that called White Gold, the history of white European |
| 1:13.8 | slaves in Africa under the Barbary pirates, the Muslim corsairs. |
| 1:21.6 | This is a long-forgotten history, and we look at how over a million white slaves were |
| 1:27.4 | taken and captured from across Europe and |
| 1:30.2 | even the British Isles, even beyond that. That's all at winston-martial.com.uk. |
| 1:38.0 | But without further ado, Charles Milton. Well, it is my great pleasure to have one of my favorite historians in the studio today, Charles Milton. My favorite because you choose all the topics that I seem to love. I first came across your work through white gold. We were discussing this before we started rolling about the slave, the European slave trade in North Africa, the over a million white slaves, which we're going to hopefully cover on another episode. |
| 2:03.9 | But what we're going to get into today is your most recent book, The Stalin Affair, The Impossible Alliance that Won the War. |
| 2:13.6 | Now, why I thought this would be interesting and why I wanted to cover it with you is because |
| 2:17.7 | one of the themes we've been exploring on the show is the post-World War II consensus. And part of that |
| 2:22.9 | was a weird relationship that the West has with communism, even with Stalin. And, you know, it's |
| 2:32.1 | perfectly normal, I think. think in London you can wear a |
| 2:35.3 | Che Guevara t-shirt you can even fly a hammer and sickle and I've seen them quite |
... |
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