WI: Cromwell's Western Design succeeded

[Wesley_Lewt]

Lets say the fleet and army sent to take Hispanolia is given adequate supplies and more competent commanders, so the army isn't malnourished and easy prey for tropical disease. They capture Hispanolia in 1655.

Western Design - Wikipedia

en.wikipedia.org

From what I have read the failure of this expedition was an enormous psychological blow to Cromwell, undermining his faith in divine providence (at least re himself). He engaged in public displays of mourning, repentance and humiliation. Both the failure itself and Cromwell's subsequent behaviour undermined confidence in his regime.

A) Would Cromwell have lived longer if it had succeeded?
B) How would its success influence British policy in the immediate aftermath and the longer term course of British history?

 

[raharris1973]

Hispaniola gets Jamaica's history, super-sized?

Maybe France gets to run a petite Haiti in Jamaica or Puerto Rico or a full size one in Cuba.

 

[LostInNewDelhi]

Cromwell and Louis XIV, as allies... God, the 1600s were weird.

 

[Strategos' Risk]

So Cromwell and Napoleon both had bad luck in attacking that island during their revolutionary reigns. How about that.

 

[The Tai-Pan]

So Cromwell and Napoleon both had bad luck in attacking that island during their revolutionary reigns. How about that.

Malaria isn't bad luck, it is endemic.

 

[NedStark]

So Cromwell and Napoleon both had bad luck in attacking that island during their revolutionary reigns. How about that.

Cromwell managed to take Jamaica, though, and it was certainly no small feat in his time.

Perhaps we can have the fleet deciding to stick to the original plan of attacking Cuba instead of Hispanolia.

 

[Wesley_Lewt]

Cromwell managed to take Jamaica, though, and it was certainly no small feat in his time.

Perhaps we can have the fleet deciding to stick to the original plan of attacking Cuba instead of Hispanolia.

At the time, Jamaica wasn't worth very much.

Dismay was the reaction in London.

They intended to take both Cuba and Hispanolia. Maybe both is too ambitious, but with adequate supplies and so significantly fewer losses from disease I think one at least was feasible.

 

[Kellan Sullivan]

Cromwell managed to take Jamaica, though, and it was certainly no small feat in his time.

Perhaps we can have the fleet deciding to stick to the original plan of attacking Cuba instead of Hispanolia.

AIUI the problem was that the English fleet took too long and the Spanish had enough time to prepare. And the only reason they "bothered" with Jamaica was to avoid having to return to London "complete failures". Jamaica was less well defended and less important than Hispaniola.

Interestingly, if Cromwell DOES take Hispaniola It removes the whole "Brethren of the Coast" from view, since that was the governor of Jamaica's way of ensuring both the "prosperity" and "security" of the new colony (by legitimizing pirates as privateers). A successful conquest of Hispaniola means that Cromwell likely devotes more ships/men to its defense, so no "Golden Age of Piracy". Least for the English.