1. What, if anything, did you know about the Rough Riders before you read this book?
 
2. Discuss the Rough Riders, where they came from, and the origin of their name. What qualities were most important for these soldiers to possess?
 
3. Did you agree with Teddy Roosevelt’s decision to resign from his civilian leadership job with the Navy and go to war as a Rough Rider?
 
4. Thinking about the Rough Riders’ mission to go to Cuba, were the soldiers realistic about the hardships they would endure? If you compare their expectations to those of other volunteers going off to war, do you see any similarities? Differences?
 
5. Roosevelt was given the command, even though he had had very little experience as an officer.  What did you think of this move, and what do you think were the qualities that made him a leader?
 
6. Discuss how Roosevelt was viewed by his men during the weeks they were together. Were there examples of how he interacted with the men that surprised you? Were there ones that made you see him as a hero?
 
7. Roosevelt angered the Secretary of War with his actions. Do you feel that that anger was justified? How do you think he should have handled the situation?
 
8. Looking at Roosevelt in 1898, would you have predicted his rise to power? How much was chance, and how much was his own temperament?
 
9. Is the picture you had of Roosevelt different from the portrait drawn here, and were you persuaded by this one? If you were to meet him, what would your reaction to him be?
 
10. Talk about the other famous men who traveled with the troops, like Frederic Remington, Stephen Crane and Hamilton Fish. How did they factor into the story of the Rough Riders?
 
11. Many Rough Riders were killed or wounded in the fighting and its aftermath. Does the author give the reader a realistic view of the hardships and intricacies of war?
 
12. Did the media overemphasize the Rough Riders’ and specifically Roosevelt’s role in victory when they returned to the U.S. in August 1898? Discuss wartime fame. Is hyperbole often part of the story?
 
13. How do you think that his role in the war aided Roosevelt when he succeeded President William McKinley following his sudden death in 1901?