Most alternate histories of the American Revolution that I’ve seen have gone in the direction of partial or total defeat for the USA. I’ve been thinking about the other direction. While things broke pretty well for the Americans, there were a few missed opportunities for the Allies, which could have pushed the tide even further in their direction:
-
In Canada they couldn’t quite pull off a siege of Quebec, and storming the city proved disastrous.
-
They were unable to send support to would-be rebels in Acadia/New Brunswick and quickly lost any opportunities they had there.
-
The French decisively lost the Battle of the Saints in 1782 (IIRC), which prevented an easy invasion of Jamaica. A Franco-Spanish siege of Gibraltar also failed, and an invasion of England never quite got its act together.
So, imagine a timeline where at least some of these occur. When the peace negotiations get undeway, the French hold Jamaica, the Spanish and French have captured Gibraltar, Yorktown has happened, the Spanish have captured British posts all along the Gulf of Mexico (as in real life). The Allies are in much stronger position than in reality.
But we know the French and Spanish were more than willing to sell out the USA, and their real-life position was that the US should be hemmed in at the Mississippi. So having a stronger French/Spanish bargaining position doesn’t necessarily help the Americans.
So, what happens next? Do the British swap Canada back to France to regain Jamaica (assuming they still have it)? Does such a decisive victory save the French monarchy? Does a US-UK rapproachment occur more rapidly in the face of the resurgent French, or more slowly since the British defeat is more bitter? Does the Spanish-American war occur around 1800 to gain access to the Mississippi?