Well, first official timeline discussion/post I made. This is a timeline loosely based on the changes of the Caribbean. It's an alternate timeline started in the 1640s, and it deals with the struggles of the Spanish, Dutch, English, and French Caribbeans. It holds lots of changes, especially with the focus of the Island of Jamaica after the 1640s. Any questions/suggestions/advice/anachronisms can be discussed within this timeline

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POD:
Pictured is Álvaro de Luna y Sarmiento, the governor of Spanish Cuba from 1639-1642
Alvaro de Luna y Sarmiento, not related to the 13th century figure, had priorities to refortify Forts in Havana due to warnings against the Portuguese and Dutch attack on Havana Harbor by June in 1642. He was granted 200,000 ducats, spent it with his lust and greed on his villa and plantation, he was not being concerned about his duties as being a governor and a protector of the island. On August 26th, a joint Dutch-Portuguese fleet arrived at Havana and bombarded the coastal cities and the fort at Coximar. The end result was the abdication of Alvaro de Luna y Sarmiento from power and subsequent execution.
On September 2nd, 1642, the Spanish elected Sebastián Fernández de Gamboa as governor of Cuba. His reign would last until 1651 as he was replaced by Pedro Benedit Horruytiner, nephew of Florida Gov. Luis Benedit and Horruitiner until May 19, 1655.
Santiago, a beautiful island in close proximity of Cuba,
Las Islas Tortugas, and Hispaniola was governed by
Diego de Villalba y Toledo, marqués de Campo from 1643-1653. A ruthless decorated knight was granted the honor of the defense of the island. His rule and decoration would lead many Andalusians and Canarians to move to Santiago, having an impact on displacing Maroons to the south central part of the island. In 1653, he was briefly replaced by Fernando de la Riva Agüero y Setien until April 15th of 1655.