Comparing Presidents Theodore Roosevelt and Woodrow Wilson

Presidents Theodore Roosevelt and Woodrow Wilson, the 26th and 28th Presidents of the United States, respectively, were influential figures who left their marks on the nation's history. Despite representing different political parties, with Roosevelt as a Republican and Wilson as a Democrat, both leaders contributed significantly to the country's development. This essay will explore their major contributions, highlighting their similarities and differences in governance.

Roosevelt: The Roughrider Diplomat

Theodore Roosevelt, assuming office in 1901 after the assassination of President William McKinley, became the youngest President at the time, aged 43.

However, prior to his presidency, Roosevelt had already experienced a life filled with remarkable achievements. He served as a Lieutenant Colonel of the Roughrider regiment during the Spanish-American War, gaining fame for leading a charge during the Battle of San Juan. His gallantry in this battle contributed significantly to his pre-presidential reputation.

Before his presidency, Roosevelt lived on a ranch in the Dakota Territory. This period followed the tragic death of his mother and his first wife, Alice Lee Roosevelt, on the same day.

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During his time on the ranch, he engaged in activities such as cattle driving, big game hunting, and the pursuit and capture of three outlaws who had stolen his boat. In 1898, Roosevelt was selected as a candidate for the New York state governorship, ultimately winning the election and serving with distinction in that role.

Wilson: The Princeton President

Woodrow Wilson, the 28th President, assumed office in March 1913. Before his presidency, Wilson held various significant positions, including Governor of New Jersey and President of Princeton University.

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He attended Princeton University when it was known as the College of New Jersey. Notably, he was the last President to travel to his inauguration using a horse-drawn conveyance.

During his time in office, Wilson navigated the United States through World War I. Initially, he proclaimed American neutrality in the conflict. However, following the discovery of the Zimmerman Telegram, which attempted to persuade Mexico to align with Germany against the United States, Wilson asked Congress to enter the war against Germany. Another noteworthy aspect of Wilson's presidency was his appointment of Louis Brandeis, the first Jewish person, to the Supreme Court. Brandeis was confirmed by the Senate in 1916.

Similarities in Contributions

Although Roosevelt and Wilson hailed from different political backgrounds, they shared commonalities in their contributions to the United States. Both leaders had extensive experience in various roles in local and national government before assuming the presidency. One common area of focus for both was the expansion of America's sphere of influence.

Roosevelt, for instance, implemented policies to regulate railroad rates, aiming to ensure fair and equitable business practices. Similarly, Wilson introduced an eight-hour workday, demonstrating a shared commitment to improving working conditions and labor rights in the country.

Both Presidents also made significant contributions in Latin America. Roosevelt oversaw the construction of the Panama Canal, a monumental engineering feat that facilitated global trade and transportation. Wilson, on the other hand, ordered the seizure of the Port of Veracruz in response to the actions of Mexican revolutionary Pancho Villa. This move demonstrated Wilson's commitment to protecting American interests in the region.

Foreign policy played a pivotal role in both Roosevelt's and Wilson's presidencies. Roosevelt introduced the Roosevelt Corollary to the Monroe Doctrine, which allowed the United States to intervene in the affairs of weaker nations in the Western Hemisphere. Wilson, while maintaining troops in Central and Latin America, continued to pursue American interests in the region.

Both Presidents also found themselves leading the nation during times of war. Roosevelt played a role in mediating the end of the Russo-Japanese War, earning him the Nobel Peace Prize for his efforts. Wilson, on the other hand, played a crucial role in the United States' entry into World War I, a decision that ultimately contributed to the Allied victory.

After the war, Wilson's Fourteen Points plan paved the way for the establishment of the League of Nations and the imposition of penalties on Germany through the Treaty of Versailles.

Furthermore, both Roosevelt and Wilson shared a commitment to the preservation of national resources. Roosevelt set aside vast tracts of land under federal protection, creating national parks and monuments. Wilson, in contrast, established the National Park Service, which celebrated its centennial in recent years. Despite differences in their approaches, both leaders recognized the importance of safeguarding the nation's natural treasures.

Differences in Approach

While Roosevelt and Wilson achieved similar results in several areas, their approaches and personalities differed significantly. Roosevelt was known for his brash and assertive demeanor, shaped by his status as a war hero. He favored a strong military and adopted a direct approach to defense matters. In contrast, Wilson maintained a more reserved and cautious foreign policy approach, even when faced with the outbreak of World War I. He initially sought to keep the United States out of the conflict until the discovery of the Zimmerman Telegram prompted him to request Congress to enter the war. Roosevelt's approach might have been more aggressive and proactive in a similar situation.

In terms of legislative priorities, Roosevelt focused on conservation efforts, environmental resources, and healthcare reform. His policies aimed at regulating businesses and ensuring fair practices. In contrast, Wilson leaned more toward economic and financial matters, implementing policies that addressed labor rights and the eight-hour workday.

One notable difference between the two Presidents was their stance on segregation. Roosevelt was the first President to invite a Black individual, Booker T. Washington, to dine at the White House. However, the public backlash was so severe that it would be nearly three decades before another person of color would be welcomed in the White House. In contrast, Wilson's presidency saw the establishment of Jim Crow laws, which legalized racial segregation and the creation of separate facilities for Black Americans. Wilson's policies, including the requirement of photographs on employment applications, exacerbated racial disparities.

Additionally, Wilson's presidency indirectly contributed to the resurgence of the Ku Klux Klan. His close friend and former classmate, Thomas Dixon, authored the book "The Clansman," which served as the basis for the controversial film "Birth of a Nation." This film, the first to be screened in the White House, portrayed the Ku Klux Klan in a positive light, leading to a resurgence of the organization.


Presidents Theodore Roosevelt and Woodrow Wilson left indelible marks on the history of the United States, each contributing significantly to the nation's development. Despite their differences in political affiliation, personality, and approach, both leaders shared common goals and made notable contributions to various aspects of American society.

Both Roosevelt and Wilson held prominent roles in local and national government before assuming the presidency. They both emphasized the expansion of America's sphere of influence, leading to advances in business, trade, and foreign policy. Additionally, they played pivotal roles during wartime, with Roosevelt mediating the end of the Russo-Japanese War and Wilson's leadership in World War I.

While their approaches differed, resulting in distinct legislative priorities, both Presidents ultimately worked toward the betterment of the United States. Roosevelt's conservation efforts and healthcare reforms and Wilson's focus on labor rights and economic policies left lasting legacies.

However, their contrasting stances on segregation and racial policies set them apart. Roosevelt's invitation to Booker T. Washington marked a brief moment of progress, while Wilson's administration saw the institutionalization of segregation and the resurgence of the Ku Klux Klan.

In conclusion, Presidents Roosevelt and Wilson, despite their divergent paths, both guided the United States through pivotal moments in history and left the nation in an improved state when they departed from office. Their contributions continue to shape the nation's trajectory and serve as enduring legacies of leadership.

Written by Emily Wilson
Updated: Jan 18, 2024
Keep in mind: this is only a sample!
Updated: Jan 18, 2024
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Comparing Presidents Theodore Roosevelt and Woodrow Wilson. (2021, Oct 11). Retrieved from

Comparing Presidents Theodore Roosevelt and Woodrow Wilson essay
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