He went to Exeter, and I think his parents were living in CT at the time. Then I think he went to Michigan for a year, cried the whole time, and then I thought he finished up at Colby. His exposure to "real Boston" is almost non-existent (in other words, if he went after the prep school / NESCAC set, I'd get it - but he mainly uses the accent, southie stereotype as his primary whipping horse). Either way, he's an insecure dude who was the type of fat and friendless outcast that desperately wanted to be one of the cool kids. All credit to him for growing up, finding a voice, and writing some pretty good stuff over the years, but found out that he could weaponize the anti-Boston stuff for clicks over the last 10 years. The rest of Deadspin followed suit, except they don't know how to at least be funny about it, and lack all ability to be self-deprecating.