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.

Theodore Roosevelt (1858-1919) was the 26th president of the United States. After becoming president following William McKinley’s assassination, he advanced the “Square Deal,” strengthened federal regulation of corporations and railroads, protected millions of acres of public land, and expanded America’s influence abroad. Roosevelt left a lasting legacy as one of the most influential presidents of the Progressive Era.

Charles Curtis (1860-1936) was a Kansas lawyer and politician who rose from county government to the U.S. House, Senate, and Republican Senate leadership. He became Herbert Hoover's vice president in 1929 and presided over the Senate during the first years of the Great Depression.

Charles G. Dawes (1865-1951) was an Ohio-born lawyer and Chicago banker who became comptroller of the currency and later a leading figure in international economic reconstruction after World War I. His work on the Dawes Plan earned him the 1925 Nobel Peace Prize, and he subsequently served as Calvin Coolidge's vice president from 1925 to 1929. Afterward, Dawes served as U.S. ambassador to the United Kingdom before returning to Chicago, where he died in 1951.