Garret Hobart (1844-1899) was a New Jersey lawyer, businessman, and Republican legislative leader who became William McKinley's vice president in 1897. He was an unusually active vice president who worked closely with McKinley until declining health forced him from public activity. Hobart died in 1899, leaving the vice presidency vacant until Theodore Roosevelt took the office in 1901.

Charles W. Fairbanks (1852-1918) was a successful railroad attorney who became one of Indiana's leading Republicans and served in the U.S. Senate. He became Theodore Roosevelt's vice president in 1905 and presided over the Senate during Roosevelt's second term. Fairbanks later ran unsuccessfully for vice president again in 1916 and died in 1918.

Thomas R. Marshall (1854-1925) was an Indiana lawyer and governor who became Woodrow Wilson's vice president in 1913. He served for eight years, including during World War I and the constitutional uncertainty surrounding Wilson's incapacitation in 1919. After leaving office, Marshall returned to law and public speaking before dying in Washington in 1925.

James S. Sherman (1855-1912) was a New York lawyer and longtime Republican congressman who became William Howard Taft's vice president in 1909. He served as a congressional leader and presided over the Senate while the Republican Party increasingly divided between Taft and Theodore Roosevelt. Sherman died six days before the 1912 election, and the Republican Party substituted Nicholas Murray Butler as his electoral running mate.

Woodrow Wilson (1856-1924) was the 28th president of the United States, serving from 1913 to 1921. His administration established the Federal Reserve, strengthened federal regulation of business, and ultimately brought the United States into World War I, after which Wilson championed his Fourteen Points and the League of Nations. His legacy is complicated by his administration’s racial segregation, suppression of speech, and expansion of presidential power.

William H. Taft (1857-1930) was the 27th President of the United States, serving from 1909 to 1913, and later became the 10th Chief Justice of the United States Supreme Court. Taft served in several important government positions before becoming president, including Governor of the Philippines and Secretary of War. As President, Taft strengthened federal antitrust enforcement, expanded railroad regulation, and promoted American economic influence abroad through his policy of Dollar Diplomacy.