Trump is trumpeting where he is going with respect to Puerto Rico: privatizing the whole place because of their crushing debt. http://talkingpointsmemo.com/edblog/getting-ready-for-trumps-puerto-rico-shakedown
Trump is responsible for some of that debt: will he pay it back? http://www.independent.co.uk/news/world/americas/donald-trump-puerto-rico-owe-33-million-golf-club-bankrupt-coco-beach-golf-club-a7970201.html
Note how the Independent is preparing the way for Trump here: they put the word “owes” in scare quotes, and identify Amy Siskind, who wants him to pay it back, as “a prominent Hillary Clinton campaigner”.