Winston’s War

Winston’s War

by Michael Dobbs

About the Author

Michael Dobbs is also Lord Dobbs of Wylye, a member of the British House of Lords. He is Britain’s leading political novelist and has been a senior adviser to Prime Ministers Margaret Thatcher, John Major, and David Cameron. His bestselling books include House of Cards, which was made into an award winning TV series in the UK and is currently being remade into a major U.S. television series by Kevin Spacey and the director David Fincher. Read more on his website:

Reading Group Guide

1. Churchill is a character who never capitulates, especially when the values he holds most dear are in the gravest danger, and even when those he counts on most abandon him. Have you ever been in a situation where you were forced to uphold a belief or moral standpoint when almost everyone you knew walked out on you?

2. Burgess is a slave to the bottle; Churchill, in a similar manner, can only function with a cigar handy and a brandy within arm’s reach. Do you think it’s at all apparent how their fondness for booze and smoking affects their decisions and their lives? Do you think there is any way in which these vices actually help them?

3. There are many love stories in Winston’s War, but none end happily. Why do you think the author chose to focus on unhappy love, and how does this choice reflect the era in which the book takes place?

4. The role of kings in politics is not often one we consider today. But the King of England is a character in this story, and one that takes the occasional dip into politics. Do you think he is able to influence the course of political events at all, to influence the minds of politicians, or is his role simply that of a passive commentator?

5. Betrayal is a major theme of the book. Are any of the characters’ betrayals justified? If not, are there any circumstances in which betrayal can be justified?

6. Mac, the barber, is one of the few characters in this book from the lower class. How does his work secretly gathering sensitive political information illuminate the relationship between the rich and poor? Do you think an upper-class person doing the same type of work would have been more quickly discovered?

7. “How horrible, fantastic, incredible it is that we should be digging trenches and trying on gas masks here because of a quarrel in a faraway country between people of whom we know nothing.” With the benefit of hindsight, we can see that there was very little alternative to war with Hitler. However, Chamberlain was forced to make very important decisions without that benefit. Did this book make you feel more sympathetic to his attempt to appease Hitler, or do you still find his motivations to be completely wrongheaded?

8. Churchill and Chamberlain are very different men, and very different leaders. Michael Dobbs does not hesitate to explore the boorish and brutish sides of Churchill’s personality. Do you think there are any ways that this darker side of Churchill made him a better leader than Chamberlain, especially during this time of crisis?

9. Was Burgess, in any sense, a patriot? Is it possible to betray your government while staying true to your country? Do you think that Burgess’s motivations to work for Russia were ultimately selfish, or that he was making a real attempt to live for ideals that he considered to be noble?

10. Of the major female characters in the book, two of them are dramatically different—one is a prostitute, the other is a spy. How do their roles in the novel reflect the social status of women at the time of World War II?

11. World War II, often called “the good war,” is widely considered to be a noble, just war that the Allies were right to fight. Yet the only character who is on the front lines throughout the book, Jerry, dies in an accidental and almost pathetic way. Why do you think Dobbs chose this death for the character, and how do you think it reflects the author’s view of the early days of World War II?

12. There is a fine line between fact and fiction. Michael Dobbs says, “This is unashamedly a novel, not a work of history.” But does a historical novelist have a responsibility to the truth? How far can a novelist change history before losing the trust of his audience?


1935 Brookdale Road | Suite 139
Naperville, IL 60563
(800) 432-7444 or 800-43Bright (toll-free)
(630) 961-3900 (phone)
(630) 961-2168 (fax)