Let's not get too excited about this. Yes, it is possible and not necessarily even uncommon to do well (whatever "well" means for each person individually) having attended a Caribbean medical school. Medical school, above all else, is an individual journey and as such a lot rests on the individual. Therefore, I would expect individual aspects to matter more than what school one attended. However, that being said, I think the general consensus is that it is safer to attend a US medical school. The attrition rates are pretty high at Caribbean medical schools and many would consider it challenging to move to a foreign island for school. Also, while there are notable exceptions, such as with SGU, the quality of Caribbean medical schools is variable. While it is indeed possible to match well as a Caribbean medical graduate, the match rates are generally a bit lower. This doesn't mean you can't get what you want, you just might have a bit of a harder time, especially with more competitive programs. Again, this is a highly individualistic journey. If you rock, you rock. However, if you are at a US medical program and you don't rock, you are probably still going to match somewhere. Competitive programs are hard for everyone, though, regardless of where you went to school.