IOTL, Spanish attempts to expand their colony of Florida further into North America were mostly thwarted by the English and French, flanking Florida through the foundation of the colonies of Carolina (in the mid-17th century), Georgia (early 18th), and Louisiana (also early 18th). Still, Spain attempted to expand Florida through a number of expeditions, such as the expedition to Georgia and South Carolina during the War of Jenkins' Ear in 1741, but to no avail.

My question is: how could Spanish Florida have expanded to encompass all or most of the territory that would IOTL become the US Deep South (Louisiana, Mississippi, Alabama, Georgia, South Carolina, maybe Tennessee and North Carolina as well)? How could the Spanish take New Orleans and the Southeastern coast (maybe all the way to the Cape Fear river) before the French and English can?

How would Uber-Florida behave as a country or political entity? What would be the Spanish colonists' relations with the Native tribes such as the Cherokee, Creek, Choctaw and Chickasaw? Would slave-dependant cash crop agriculture still spread?
 
To get Spain to take French territory iOTL is kind of tricky, since the 1700s started off with a brand-new Bourbon King in Spain. Maybe if the Hapsburgs win the War of the Spanish Succession you might have a more British-aligned Spanish monarchy, but that sets off so many butterflies who knows.

As for British territory, maybe if you'll keep Oglethorpe's strict provisions prohibiting slavery, supporting Natives and banning all sorts of stuff you'll keep the Province of Georgia feeble enough that it is seen as a cash drain and its few hundred inhabitants are ceded by Britain in return for some Caribbean island in the case of a particularly close war that ends in British victory. Seems pretty factible to me.
 
A rather simplistic solution would be the Ayllón expedition to succeed so the Spanish fund a colony in South Carolina in 1526. The colony was planned to be a settler colony instead of an exploitation one. I guess the Spanish settlers would expand northwards along the coast to further protect the colony and Florida. We could easily have the Spanish clonies to clash with English or French ones between North Carolina and Virginia. If we also make the De Luna colony succeed some decades later we could have the Spanish secure the Mississipi far before the French funded Quebec.
 
It wasn't so much that Spanish efforts were thwarted, but rather that Spanish efforts were too little, too late. They held Georgia, but didn't do anything with it other than attempt to convert the natives to Christianity. Subsequently, the English sponsored their own native allies to destroy that system. Afterwards, Spain waged a losing battle to retain what they had. In the west, Spain failed to secure the entire gulf, and France worked its way in, securing a foothold in Mobile, then New Orleans.

You can't really fault the Spanish. They had a huge empire and Florida didn't hold any real attraction. Lots more lucrative options elsewhere.

the Yamasee War of 1715-1717 came within a hair of wiping out South Carolina. Ultimately, Spain was unable to effectively aid the natives looking to destroy the English colony. French efforts in Mobile/Biloxi/New Orleans were still in the fledgling stage. This was an optimum time to regain control of the region. Unfortunately, France and Spain were nominal allies at the time, and Spain was devastated by this little thing called the War of Spanish Succession, and had its eyes on the more pressing matter of regaining Italian lands.

Post American Revolution, Spain claimed most of Tennessee, Georgia, Mississippi, Alabama, Florida, and the Louisiana territory by right of conquest. Post Seven Years War, they claimed everything west of Appalachian Mountains by right of treaty with France (Britain only recognized west of Mississippi River). 7YW is rather tough, as Spain had just got it's arse handed to them (which is how they ended up with Louisiana). Post AR, if Charles IV had been a worthy successor to Charles III, perhaps Spain could have stood up to a young war torn nation and made good its claims.

So, your best bet is an earlier/better settlement of the region so that it can resist encroachment of the English/French and weather the destructive results of the WoSS.
 
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