Puerto Ultimo
Location: Puerto Rico
Population: 750,000
Government: Despotism
The Serpentfall devastated Puerto Rico, of course. San Juan and the other cities on the north coast were obliterated; Aguadilla and Mayaguez on the west, merely hammered and half-destroyed. But the mountains protected the cities in the south, and the Puerto Rican colonial government under Tugwell successfully relocated to Ponce on the south coast, which is now the ‘provisional’ capital. Rexford Tugwell remains colonial governor, mostly because the US Naval units at the Roosevelt Roads naval base (itself a consolidation of surviving American military units in the Caribbean) unquestionably back his rule.
Governor Tugwell is an organizer, and the remarkably high number of people still alive and working in Puerto Rico is a testament to his skills. He also maintains a close relationship with both Roosevelt Roads, and US Navy forces in Panama. Tugwell even has the official sanction of what’s left of the United States, thanks to his active work in sponsoring and supporting a variety of groups countering both Axis and Russian South American spy networks (the OSS runs its South American operations out of Guayama). But all of that cooperation comes with a price: Governor Tugwell’s word is law in Puerto Rico, and he serves at his own pleasure.
In the OTL, Rexford Tugwell went on to join the Progressive Party in 1948, and continue to espouse central planning policies until his death. Whether or not this tendency has led the governor in the DAR timeline to a dangerous flirtation with — or secret surrender to — the Red Menace is up to the individual GM. Even if he is not a secret Communist working with the Iowa Soviet or the Soviet Union or Cuban guerrillas (or simply planning his own Red Revolution), Tugwell is increasingly regulating the lives of the native population of Puerto Rico. The current situation may even warrant a heavy (and skilled) hand, but if that ever changes (or Tugwell makes enough wrong decisions), there could be serious trouble on the island.
There are a lot of groups and not a few countries who would like there to be trouble on an island that is currently serving as the northeast defenses of what remains of the US Navy in the Caribbean. This would remain true even if the governor is a secret Red. Perhaps more true, really: even as a Communist, Rexford Tugwell would be just a little too independent-minded to suit the Soviet Union. Of course, Comrade Stalin has a certain saying about how to handle such problematic men as that.