The Great Day in My Life: Theodore Roosevelt, the Charge at San Juan Hill, and Courage

In this lesson, students will learn about Theodore Roosevelt, who exercised courage to overcome illness and to lead troops in Cuba. They will also consider how to cultivate and apply courage in their own lives.

Walk-In-The-Shoes Questions
As you read, imagine you are the protagonist.

• What challenges are you facing?
• What fears or concerns might you have?
• What may prevent you from acting in the way you ought?

Observation Questions

• What contributions did Theodore Roosevelt and the other American soldiers make to the advancement of freedom through their demonstration of courage in Cuba?
• In what ways did Roosevelt’s courage contribute to his ability to lead his men in Cuba?

Discussion Questions
Discuss the following questions with your students.

• What is the historical context of the narrative?
• What historical circumstances presented a challenge to the protagonist?
• How and why did the individual exhibit a moral and/or civic virtue in facing and overcoming the challenge?
• How did the exercise of the virtue benefit civil society?
• How might exercise of the virtue benefit the protagonist?
• What might the exercise of the virtue cost the protagonist?
• Would you react the same under similar circumstances? Why or why not?
• How can you act similarly in your own life? What obstacles must you overcome in order to do so?

• Students will evaluate Theodore Roosevelt’s courage during the Rough Riders’ battles in Cuba.
• Students will analyze how courageous acts can promote progress.
• Students will apply their knowledge of courage to their own lives.