Have you thought about collecting your debt with several sessions with him?
crazy that in this buyers market some guys are short minded to do something like this. 300 a week = 1,200 a month... He grabbed 300 and lost thousands.
I'm glad it worked out! How come he had to ask you for $ for medicine, groceries, a Halloween costume and Uber? Doesn't have a CC, some bank accounts and some money hidden somewhere for a rainy day and specially for his future?