Boston.com  summed it up well, when they said:"On the scale of how “Boston” a celebrity is, Jake..." "is more Jimmy Fallon than Mark Wahlberg. It’s more of a Boston-at-heart kind of deal for the non-local.

They mentioned about Jake's summer's on the Vineyard"

“Every time I fly over… I land in Boston and drive to the Cape or wherever I go, that drive is always where I feel like my heart is here.”

"He couldn’t tell you where the nearest T stop is if he tried, but, after chatting with him last weekend, I can say he’s as blunt as any Bostonian fighting for a seat on the Green Line."

Jake wouldn't attempt a  Boston accent (“give me three months of preparation, I think I might be able to pull it off,” he said),

 They go on to say that he "is probably used to being on the receiving end of some good-natured ribbing from his long-time best friends who hail from Massachusetts. They aren’t afraid to give him the business when it comes to sports and pretty much forced him into becoming a member of Red Sox nation."

“Some of my closest friends all lived and grew up in Boston or around Boston,”  “So, just due to the fact that they are all my boys and they’re all Red Sox fans, I’m a Red Sox fan. I have to be. I have no choice even though I live in New York.”

 So that's the only reason you keep wearing this?

 So the Yankees cap is the one your forced to wear for work?