Here's one further back, then:
1897-William McKinley (R)
1901-Theodore Roosevelt (R)
1909 William Howard Taft (R)
1917 Theodore Roosevelt (R)
1921 Champ Clark (D)
1921 William Randolph Hearst (D)
1929 John J. Pershing (R)
1941 Wendell Wilkie (D)
1942 Juan Trippe (D)
1949 Edsel Ford (R)
1961 J. Patrick Kennedy II (D)
In 1912, despite feeling great degree of animosity towards President Taft, former President Roosevelt decides against mounting a challenge for the Republican nomination. In the most narrow of elections, Taft defeats William Jennings Bryan. Taft's second term see's a number of new reforms, but the bulk of his second term is spent at once making every attempt to avoid entry into the conflict in Europe, and due to pressure from the Roosevelt faction, making some efforts to prepare the nation for that eventuality. In 1916, former President Roosevelt announces that "My hat is in the ring!" He is handed the nomination on a silver platter. Roosevelt defeats New Jersey Governor Woodrow Wilson and begins the first third term in American political history.
Naturally, the term is mostly devoted to the American war effort oversees. Roosevelt manages to obtain a declaration of war against Germany early in his third term. Though Roosevelt promises reform in the 1916 campaign, the war derails any progressive effort by his administration. Despite America's victory in that war, Roosevelt declines to run in 1920. Champ Clark, who lost the nomination to Bryan in 1912, is nominated by the Democrats. After 24 years of Republican control of the White House, incumbent fatigue leads to Clark's victory over Charles Evan Hughes. Clark had the single shortest Presidency in American history, dying on March 6th 1921, just two days after his inauguration.
The twenties would instead be dominated by Clark's Vice President, Media tycoon William Randolph Hearst. Hearst's conservative economic policies help to usher in an economic boom period. Despite his advanced age, war hero General Pershing wins the election of 1928 in a landslide. When the economy collapses in 1929, Pershing tirelessly works to restore the American economy. Affectionately known as "The General" He is reelected in 1932. In 1936, Pershing decides to go for a third term. By the end of Pershing's third term the depression seems to be coming to an end.
Wendell Wilkie, a Democrat who sympathizes with some of the reformist elements of the Pershing government wins the election in 1940. He suffered a heart attack a year into his term. Juan Trippe's term as President, like Roosevelt's third, is mostly focused on a chaotic situation in Europe and in the far east. Edsel Ford, a Republican in the McKinley mode, is elected in 1948. Like General Pershing he proves to be extraordinarily popular, serving three full terms. Kennedy, a conservative democrat firmly in the Hearst mode, wins in 1960 cementing the Democratic party's reputation as the fiscally conservative party in the US.