the western design

I´m wondering what could happen if the plans of oliver cromwell succed. What if Venables and Penn had been in a better relationship. What if they really succed in the conquer of Sto. Domingo instead of Jamaica. I believe that a conquest, relatively easy, of the island would mean that British troops would be less decimated and much more moral, and may even try the assault on the island of Jamaica and even Cuba. Furthermore, a more developed empire in the Caribbean, would have involved a radical change in the pattern of English colonization, that would lead to a smaller or at least, less important presence in North America, perhaps allowing a better resistance of the French military in the inevitable crash in the area between this two powers.
The sucess of Venables and Penn could might have encouraged more plans of conquest like the one that pretended to take Venezuela, land that only could be supported (by the Spanish) with metropolitan reinforcements because of the winds of the zone, and therefore, could become a consolidated conquest before the Spanish counterattack so more territories in the Caribean, more settlers and less importance of North America.
What do you think?
 
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A success on Santo Domingo is possible, if one were to make the English even remotely competent.* Have a supreme authority chosen (or Penn and Venables get along, or don't deploy them); sack the comissioners, especially Butler; properly provision and equip the army; and have the actual military portion carried out in an efficient manner: come ashore, storm the port, and keep some sort of discipline, resolution, and above all, competence.

I don't see the expedition being able to carry out too many future conquests, though. The spanish defenses in the Caribbean were not notably strong, but they are probably strong enough to hold, say, Cuba against a continued English attack. Probably, the english are left holding Santo domingo (and perhaps the rest of the island), maybe Jamaica as well, and keep them once the european war is over.



*Though, that being said, the way that the expedition was actually handled I'm a little surprised that they managed to take even Jamaica.
 
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