American Portraits

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.

Founding Principles

Individual Responsibility image

Individual Responsibility

Individuals must take care of themselves and their families and be vigilant to preserve their liberty.

Private Virtue image

Private Virtue

The idea that only a knowledgeable and virtuous citizenry can sustain liberty.


On April 25, 1898, Congress declared war, blaming the Maine explosion on Spain. The Assistant Secretary of the Navy Theodore Roosevelt was not content with a desk job ordering fleets around on a map and felt compelled to go to war. He stated, “It does not seem to me that it would be honorable for a man who has consistently advocated a warlike policy not to be willing himself to bear the brunt of carrying out that policy.” Moreover, Roosevelt believed men and nations ought to follow “the soldierly virtues,” and sought to test himself in battle and win glory….

Narrative PDF

Compelling Question

How can your courageous actions help to advance freedom in your life and the lives of others?

Virtue Defined

Courage is the capacity to overcome fear in order to do good.

Lesson Overview

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.


  • 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.


In 1896, William McKinley was elected president. At that time, the Cubans had begun to rise up against Spain, which had colonized the island during the height of its empire in the 1500s. Thousands of Cubans valiantly fought a guerrilla war against the Spanish, who sought to quell the rebellion by placing more than 100,000 Cubans in relocation camps. McKinley eventually dispatched a U.S. warship, the Maine, to Cuban waters in Havana harbor. On the evening of February 15, 1898, the ship suffered a massive explosion that blasted it apart and left 266 American sailors dead. Although the explosion was later ruled an accident, the American press blamed Spain and called for war in an extreme and sensationalist style of reporting called “yellow journalism.” Giving in to public pressure, on April 11 President McKinley asked Congress to declare war on Spain, which it did on April 25. As a result of the American victory in Cuba, the Philippines, and other Spanish possessions, the United States became an expansionist power with ownership or influence in the former Spanish possessions of Cuba, the Philippines, Puerto Rico, Guam, and Hawaii.

Born in New York City in 1858, Theodore Roosevelt was the scion of a wealthy family. He was a sickly child who suffered from asthma, but he strengthened his body through a rigorous program of physical activity. As a young man, he graduated from Harvard and then became a New York Assemblyman, head of the U.S. Civil Service Commission, and the New York City Police Commissioner. However, he was also a rancher out West who loved to test himself against the harsh environment of frontier life. He was a voracious reader and wrote many books and periodical pieces. Roosevelt was the Assistant Secretary of the Navy when the Spanish-American War erupted. When the Secretary of the Navy was away for the weekend, Roosevelt re-positioned American fleets near Cuba and the Philippines to capture the islands quickly in the event of war. Roosevelt fought courageously in the war on the front lines and became a war hero. He was soon elected New York governor, vice-president, and president. Throughout his life, he promoted an active and vigorous life of physical exercise and martial virtue.


  • Colonized
  • Valiantly
  • Quell
  • Yellow journalism
  • Expansionist
  • Scion
  • Voracious
  • Martial
  • Ivy League
  • Embarkation
  • Amphitheater
  • Artillery
  • Shrapnel
  • Reproached
  • Strenuous
  • Enraptured

Introduce Text

Have students read the background and narrative, keeping the Compelling Question in mind as they read. Then have them answer the remaining questions below.

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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?

Additional Resources

  • Brands, H.W. TR: The Last Romantic. New York: Basic Books, New York: 1997.
  • Morris, Edmund. The Rise of Theodore Roosevelt. New York: Ballantine, 1979.
  • Roosevelt, Theodore. The Rough Riders. New York: Da Capo, 1990.
  • Thomas, Evan. The War Lovers: Roosevelt, Lodge, Hearst, and the Rush to Empire, 1898. New York: Back Bay Books, 2010.

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