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Interestingly I am also doing some research on the Barrow & Andrade families, the boys having gone to Wolmer's between the late 1800's and the mid 1920's.
Ivan Barrow & his brother Frank were from Morant Bay and Jewish. Ivan was an accountant and businessman having done an apprenticeship. Both played cricket and Ivan distinguished himself for the West Indies team. Frank I believe was an attorney.
The Andrade's I am having less 'luck' with .
The only 'Wolfe' I have come across was an Ellis Wolfe, a Jewish benefactor of Wolmer's Boys' School in the 1800's from the UK who had multiple business interests in both places and bestowed a lot of resources to many causes some of which were to aid Jews.
Those other names are not familiar to me. I know the Melhados were Jewish merchants but have yet to find a link outside of Browns Hall. Good luck on ur search though