When William McKinley was assassinated in 1901, young Theodore Roosevelt 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.

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. For over a decade, 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.