Thanks for the bump, Dan (you da man!). First off, I see this bird as clearly a Tyrannus structure-wise. Looking at Tyrannus options in Hispaniola, you've got Gray KB, and Loggerhead KB. Now I can't find any pictures specific to the Hispaniolan race gabbii, But all photos and guides I can find show Loggerhead missing the (full) white cheek that is found on Gray. This bird has that same white cheek. Gray KB for me - that's my take on it, anyway.