1. At the novel's end, George Smiley, the spymaster observes  that "an old spy in his dotage seeks the truth of ages." Leaving the import (or meaning of that statement) for the time being, let's turn to Peter Guillam. How much "in his dotage" is Guillam? Is his memory dulled by age, or is he still as sharp as a knife? How much does he pretend to be struggling to keep up?

2. Guillam, at one point expresses his "outrage at having my past dug up and thrown in my face." What is the past that is being brought to light? (This might be a tougher question than it seems on the surface.) What was Windfall — what happened and what was supposed to happen? Who was responsible for it?

3. In the letter which summons Guillam back to England, A. Butterfield (who later is humorously known as "Bunny"), refers to "a matter in which you appear to have played a significant role some years back." What was Guillam's role in all that transpired, and how "significant" was his involvement?

4. The book's narrative technique includes Guillam's own memories interspersed with the content of old files —  documents, memos, and letters, even audio tapes. Did the back and forth between memory and files make it difficult to follow the story?

5. Alec Leamas is the hero of le Carre's famed 1963 book, The Spy Who Came in from the Cold. How would you describe Alec? Does it help to have read the earlier book to understand his character, or is there enough detail in Legacy to give a full portrait of Alec? What was the relationship between the two men, Alec Leamas and Peter Guillam, both professionally and personally?

6. Smiley says at the end of the novel that his ideal had always been that of "leading Europe out of her darkness toward a new age of reason." Hadn't Europe been led into the age of reason following World War II and the defeat of Nazism? What does Smiley mean and did he succeed?

7. Reverting back to Smiley's statement in Question 1, regarding old spies seeing "the truth of ages," what does Smiley mean? What is the truth of the ages?

8. Follow-up to Question 7: Perhaps the most important question of the book is this one, which Guillam poses to himself after meeting with Smiley: “How much of our human feeling can we dispense with in the name of freedom … before we cease to feel either human or free?” Did the ends justify the means in Windfall?