William Triumphant
1885-1885: Grover Cleveland/Thomas A. Hendricks (Democratic)
*1885-1889: Grover Cleveland/none
1889-1893: Grover Cleveland/Allen G. Thurman [1]
1893-1897: James G. Blaine/Ira Joy Chase (Republican) [2]
1897-1899: William Jennings Bryan/Arthur Sewall (Democratic) [3]
*1899-1901: William Jennings Bryan/none(Democratic) [4]
1901-1905: William Jennings Bryan/Charles A. Towne (Democratic) [5]
1905-1909: William Jennings Bryan/William Morris Stewart(Democratic) [6]
1909-1917:William Jennings Bryan/Charles Nathaniel Haskell (Democratic) [7]
1917-1921:William Jennings Bryan/Willard Saulsbury, Jr.(Democratic) [8]
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[1] Cleveland wins New York, and thus the Presidency.
[2] Blaine is blamed for widespread corruption and the bad economy by the Democrats (sound familiar?) and is thrown out after a term.
[3] The major events in Bryan's first term are the Cuban War, and Free Silver. The first is a success, and he is hailed as hero in Cuba and the Phillipines.
[4] Sewall dies earlier due to the intense stress as Vice-President.
[5] Bryan's second Veep is Republican-turned-Democrat Towne, who's presence draws in disaffected Republicans and some New Yorkers. The major conflict in this is the German-Venezuela War, wherein a chain of hilarious events blundered them into war and after a year they came to the negotiating table.
[6] Bryan becomes the first President to stand for a 3rd term, and the first to win one. His choice of William Stewart as VP signifies a turn to the Western states, as the last mainland territories become state (In order: Oklahoma, Sequoya, Arizona, and New Mexico). Senate reform, Women's suffrage, and Prohibition is passed by Congress and the states ratify it by the next election. The Anti-Trust Battles take up most of the last of the Bryan term, with him fighting his own party over what to do with it.
[7] The first time since the Blaine Administration, the Republicans have the House and Senate, but lose the Presidency to Bryan for a 4th time, ironically being helped by Conservative Democrats bolting over his 4th term, and unwillingness to fighting harder for segregation. It's hypothesized that only his reputation for women's suffrage saved him from losing. The Great War in 1911 spreads like wildfire over Europe, and with perceived German aggression against the rest of Europe, the Bryan administration blockades them. Scandal broke out when it was revealed the German Ambassador spoke with Southern Democratic Governors of the possibility of a coup against Bryan. War was declared early 1913, and the war ended in Entente favor January 12th, 1914. While little else happens over the 4th term, aside from his liberal use of the Sherman Anti-Trust Act, Bryan breaks another record set by Washington by appointing all 9 Justices on the court late in his 5th term.
[8] Due to war fever, Bryan is elected to his 6th, and last, term. The Democrats win Congress once more under him, and pass a Child Labor Amendment. By his 22nd year in office everyone was tired of him, even his supporters regretted electing him in the light of victory. Even he was tired of being President, but held out until 1921. He was dead within a few months after the inauguration of his successor...