This chapter contains some of the most bizarre partitioning ever, but it actually is totally logical, ITTL. The butterflies in this TL are already massive and create an almost unrecognizable 1800+. Any suggestions welcome! 
Also, I have this whole TL mapped out in my head up to (currently) 1960! I'm definitely moving this universe toward an horrifically Orwellian future in every paragraph.
War of 1812: Caribbean Theatre
British command in the Caribbean following the destruction of the Royal Navy fell to General Edward Michael Pakenham, who had decided to hold up in the Bahamas to fend off repeated Georgian expeditions launched from Florida to capture the islands. He barely held the line in late 1812 when a force under General Arthur Alexander assaulted Nassau by sea. Grudgingly, Alexander turned back to regroup his forces after a failed beach landing. Thomas Bragg, father of the later famous Braxton Bragg, marched a large Carolinian army down the coast to board the allied Georgian navy for an a new attack.
Edward Pakenham
Arthur Alexander
On the day before Christmas, the Southron forces landed and finally chased Pakenham out. Several thousand British died over the next few days of island hopping. A small Spanish fleet gave chase off the coast of Cuba, forcing Pakenham to flee to Jamaica, the last real British stronghold in the Caribbean. Georgia left a sizable force to occupy the Bahamas and then sailed down with a few Spanish and French ships to lay siege to the island. Abruptly, facing starvation and defeat, Pakenham's rowdy militiamen turned on him and his few actual remaining English soldiers and handed them over to Alexander.
Pakenham's Lobsterbacks are massacred by the Jamaican Militia
Intensive talks ensued about the island's future, and the new "leader" of Jamaica, Henry Boniface, pleaded for independence and allegiance in return for not having an occupying force ravage the former Redcoat colony. Andrew Jackson stubbornly refused, claiming that Jamaica should be the Carolinas' reward from for undercutting Britain's cotton and tobacco prices before. Georgia squawked over it and negotiations went back and forth. Finally, Napoleon stepped in and said he would grant their independence as a satellite of both Georgia and the Carolinas. Boniface became Minister Prime of Jamaica. A new country was born.
Flag of Jamaica
Minister Prime Henry George Boniface of Jamaica
With the Allies clear of having to occupy Jamaica and with the Bahamas in hand, they were free to declare open season on the rest of the British colonies in the New World. France and Spain had pressing matters in Europe to attend to, so it left Georgia and company to pick from the island buffet.
Andrew Jackson immediately annexed Saint Kitts and Nevis, Barbados, the Virgin Islands, and Antigua and Barbuda. Georgia, still under the fiery 82 year-old Prime Minister Bulloch, resented this and sent Arthur Alexander to snatch up Saint Vincent and the Grenadines, as well as Grenada and the Cayman Islands. They then disputed Saint Lucia with Jackson, but finally let the Carolinas have it in exchange for some new trade rights. Spain at first did not like this, but let it go as they hurried and retook Trinidad and Tobago before "Andy the Island Emperor" could sink his expansionist Southron jaws into it.
Napoleon, at this point in time, finally agreed to follow through on his promise to reward Jackson for his compliance with the undercutting of Britain's prices, and arranged for France and Holland to pull out of the Leeward and Windward Islands, forming the Carolinian Virgin Islands. The Dutch and French citizens on the island cluster weren't wild about this, so Jackson granted them an appearance of independence as the Virgin Islands Confederacy, while they essentially became his personal property and he appointed Thomas Bragg as Governor-General.
Thomas Bragg lands to assume command of the Virgin Islands
Thomas Bragg, Governor-General of the Virgin Islands Confederacy
Upon Jackson implementing the bizarre form of self-government in the Virgin Islands, the Confederation of the Carolinas' Congress flew into a constitutional crisis. They managed to agree to it for the moment after several emergency meetings, but they were kicking the can down the road for further (much larger) problems.
Virginia got in on the game late, but Vice President Monroe suddenly offered a very large sum of cash and cotton and tobacco to Spain in exchange for Cuba. Spain, in the bowels of bankruptcy, almost agreed, but decided to reject the offer at the last minute because of the excellent tobacco crops grown on the island.
The new "territories" were not referred to as colonies by the new administrators, which helped keep them under control, especially as slaves were brought in again to make sure the islands fulfilled their entire reason for existence: agriculture. Slaves that had been free under British rule were allowed to keep their freedom, though they were in the absolute dregs of society. France had no qualms about slavery's expansion, as Napoleon had re-instituted the system himself in Haiti and Louisiana.
The Caribbean Theatre of War had, with the exception of a few roaming British holdout guerrillas, been ended by mid-1813, in a resounding but bloody Allied victory. Now the war would shift north, to Canada, and the Republican Union...
