alternatehistory.com

during the Anglo-Spanish War 3 tries were made by the English to take the island of Puerto Rico, November 22, 1595, Sir Francis Drake and Sir John Hawkins attempted an invasion of the island with 26 vessels, when it failed they burned San Juan, Sir Francis Drake tried again in 1596 and died shortly there after, and lastly on June 15, 1598 George Clifford took and held the Island for a number of months till bacillary dysentery forced him and his men to leave, so is there any way for Drake to take the island or Clifford to hold it over the long term, more or less making Puerto Rico into Jamaica 60 years before the Brits took Jamaica in OTL?
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