This map courtesy of UnusualMaps.com illustrates the average number of medals won per million people in an Olympic Summer Games between 1996 and 2004.
Medal counts from the last three Olympic Games were used primarily due to the fact that participating nations have remained relatively unchanged during this time period. (Prior to 1996, the former Soviet Union teams participated as one team.)
Looking at the data used to create the map Trinidad and Tobago is ranked number 12 with a population of 1.33 million and 5 Olympic medals with an average of 1.25 per million per game.
Notable neighbors within the top ten sees the Bahamas first averaging 5.05, Cuba second with 2.40 and Jamaica coming in fourth with 2.21. Closer to home we have Barbados in the sixteenth position with 1.13.
I wonder where we would stack up if they took into account the total size of the country also.