Charles River Editors

For a man who grew up to become the “Bull Moose”, Theodore Roosevelt was a sickly child, suffering from asthma and other maladies. But his physical weakness actually drove him to be more active, which also fostered an interest in nature. It also helped that Teddy’s family was wealthy, allowing him privileges including home school and the ability to attend Harvard, where he was an athlete and took an interest in naval affairs. After finishing at Harvard, Teddy entered politics, but it didn’t stop him from writing The Naval War of 1812 in 1882, establishing himself as a professional writer and historian.

In the 1890s, it was Teddy’s turn to make history, leading the Rough Riders during the Spanish-American War and being decorated for his service with a Medal of Honor. He parlayed his glory into the governorship of New York and then the Vice Presidency under William McKinley. When McKinley was assassinated in 1901, young Teddy was thrust into the presidency, one that would earn him a place on Mount Rushmore, Roosevelt’s “Square Deal” domestic policies favored average citizens while busting trusts and monopolies. Roosevelt also promoted conservation as an environmental stance, while his “speak softly and carry a big stick” foreign policy is still an oft used phrase today. Roosevelt even earned a Nobel Prize during his presidency. 

As one of the most influential men of the 20th century, there is no shortage of adjectives to use when describing Woodrow Wilson’s two terms as president of the United States. Wilson was a pioneer of the Progressive movement both before and during his presidency, becoming a populist champion a generation before Franklin Roosevelt’s New Deal. He ran for reelection by touting his neutrality during World War I, only to lead his nation into the war and become the architect of a world body that would lead to greater inter-connection among nations. Today Wilson is best remembered for his Fourteen Points, one of the most forceful arguments for an idealistic foreign policy in American history, and his fight for the League of Nations, which set the model for today’s United Nations.

Wilson’s presidency was monumentally consequential, but it is not without its critics, nor is the man himself. Even as Wilson has come to be viewed as one of America’s greatest presidents, perception of Wilson and his administration as racist have also taken hold. Despite being one of the early 20th century’s most forceful proponents of a globalized foreign policy, Wilson’s personal views and comments were ardently anti-immigration, and Wilson’s administration entrenched and expanded segregation in the federal government.

Franklin Delano Roosevelt might be America’s greatest 20th century president, but there’s no question that he was the most unique. A well-connected relative of Theodore Roosevelt, FDR was groomed for greatness until he was struck down by what was widely believed to be polio at the time. Nevertheless, he persevered, rising through New York politics to reach the White House just as the country faced its greatest challenge since the Civil War, beginning his presidency with one of the most iconic lines ever spoken during an inaugural address. For over a decade, President Roosevelt threw everything he had at the Great Depression, and then threw everything the country had at the Axis powers during World War II. Ultimately, he succumbed to illness in the middle of his fourth term, just before the Allies won the war.

Kennedy has been nostalgically and fondly remembered for his youth, vigor and sense of unfinished potential, but it would be President Johnson who would bring much of the agenda to fruition. He pushed through a progressive social agenda that formed the backbone of modern American society. Known as the Great Society, the legislation included the landmark Civil Rights Act of 1964, as well as the establishment of Medicare, environmental protection, and more.

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