What Caribbean nation has won the most medals in the Olympics?

Question

Summer Olympics and Winter...

I know that Jamaica has won 42 total to Trinidad's 12. I don't know though out of all of the west indies which island has won the most?

Answer 1

It doesn't matter - Jamaica has the best bobsled team!

Answer 2

Depending on how far you push the definition of West Indies, Cuba's 165 medals could be considered as the top total.  If not that, then Jamaica's 42 would be the highest.

Answer 3

I'm pretty sure that Jamaica holds the most.