With both the Senate and the Presidency coming into Democratic-Republican hands for the first time, the lame duck Senate and the departing President Livingston fill as many vacant offices as possible. Unlike the situation in 1801 in OTL, since the Federalists already did not have control of the House, no new offices were created, so there are no unsigned appointments left uncompleted when James Madison takes office.
1809 proves to be a solemn year. On April 30, twenty years to the day when he took the oath of office of President, George Washington dies. Washington is buried at Mount Vernon, alongside his wife who died four years earlier. (Three years later than in OTL.) Nor was he the only Founding Father to die. Thomas Paine dies on June 8 (as in OTL). And then on July 16, Thomas Jefferson, died. These deaths, along with the change in administration make 1809 a commonly used dividing point in United States history in the future, depending on whether the War of 1810 is included in the initial phase of United States history.
The spark for the War of 1810 is the West Florida Rebellion. Settlers from the United States organize a rebellion against Spanish rule (hardly the only rebellion in Spanish America in 1810, but for the United States, the only one that mattered.) Actual fighting doesn't start until the taking of Baton Rouge by the rebels during September, so as a campaign issue it mainly affected the southern States due to time for the news to travel, and is not a party issue in the election of 1810. The Federalists gain in the mid-term elections, but they fail to retake either House of Congress.
Speaking of which, the short-lived Republic of West Florida is admitted as the State of West Florida by Congress on November 30, over the objections of President Madison. As admitted, West Florida includes all of the former British colony of West Florida (both the portion of West Florida that the Spanish had regained from the British in 1783, and that portion held by the United States since 1783). That annexation is generally regarded as the start date of the war, altho the formal declarations of war aren't issued by the supporters of Ferdinand VII until 1811.
At first, the British see little profit in fighting the Yankees and the Yankees see no reason to expand their war beyond Spain. Initially the war goes well for the Americans as they seize New Orleans, St. Louis, and St. Augustine in the early part of the year.
The U.S. Navy has a good year in 1811 as it is facing only remnants of the Spanish Navy that have chosen to support the Bourbons and oppose Joseph Bonaparte as King of Spain. While Joseph doesn't recognize the legitimacy of the American annexation of West Florida, as long as the Americans are only harrying the supporters of the Spanish Bourbons, he's willing to not bother with declaring a war he is in no position to fight anyway. Besides, his older brother Napoleon hopes that the Americans can be enticed into fighting the British. That may happen, but not because of anything the Bonapartes do.
As in OTL, Tecumseh's War comes to a boil in 1811. Fewer U.S. forces are in the area, so the Battle of Tippecanoe is fought with roughly equal numbers instead of the 2:1 U.S. advantage in OTL. Governor Harrison of Indiana Territory dies in the battle and never will be President.
While the British saw no profit in helping the Spanish Bourbons, the same can not be said of the Indians. By spring, they are providing arms and ammunition to Tecumseh's Confederacy at very liberal terms and the entire American Northwest was aflame with war. By the end of summer, not a single white settlement remains north of the Maumee River in Detroit Territory, and Vincennes, the capital of the Indiana Territory has been burned to the ground. Whether to declare war on the British in addition to the Bourbons will be a major issue in the 1812 elections, though both parties are split by the war.
On the Democratic-Republican side, the War Hawk faction led by the youthful Senator Henry Clay of Kentucky wants to declare war on Britain as well. The Old Democrat faction led by Speaker Nathaniel Macon wants to fight only one war at a time. Because of his initial opposition to the West Florida annexation and the disasters in the Northwest, President Madison has no support for a second term among the Democratic-Republicans. Both factions favor continuing the war with Spain.
Conversely, the Federalists are united in opposing war with Britain, but split over the issue of war with Spain. Vice President James Hillhouse leads the Loyal Opposition faction that favors the war with Spain, but sees no reason to risk war with Britain. Governor Caleb Strong of Massachusetts opposes both war with Britain and the Bourbons.
In the end, three tickets end up running. Running under the War Hawk banner is the ticket of Henry Clay of Kentucky and Representative Langdon Cheves of South Carolina. Speaker Nathaniel Macon decides not to risk his base of power in the House and instead forges a fusion ticket that supports war with Spain but opposes getting involved in a war with Britain right now. Running under the Federal-Republican banner is the ticket of Vice President James Hillhouse and Secretary of State James Monroe. Finally, running under the Liberty banner in just the nine northeastern States was the ticket of Governor Strong and Governor Roger Griswold of Connecticut.
(Note: In several states, electors were elected as part of either Federalist or Democratic-Republican slates which then fragmented between two tickets.)
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Griswold's death in late October has the effect of scattering his electoral votes, but since his ticket came in third, it has no effect on the outcome.
The Democratic-Republican controlled Senate initially favored a gentleman's compromise of picking the Democratic-Republican Vice President from the other ticket, but Governor Griswold's untimely death reminds them that it is possible that it could matter who wins the Vice Presidency, and they elect James Madison on the first ballot by the margin of 20-16.
In the House, the initial ballot is 8 States each for Clay and Hillhouse, with New Jersey split and Rhode Island supporting Strong. On the sixteenth ballot, one New Jersey Representative and both Rhode Islanders switch, giving Hillhouse the 10 States he needs.
However, despite his victory, in the 13th Congress, the War Hawks will control the House while the Senate will be a chaotic mess as no faction has a majority, and it is unclear whether the election of 1812 presages a permanent shift in political parties or not.