Really don't like the comments from the kid, but, I think his quote means something different than how it's being portrayed (not that it's any better).
Kyrie is saying that Boston is a better place to live, in that, it's a "real live (sports) city." He goes on about the "food" and "culture" and compares the nightlife between the two cities.
I personally hate Boston, wouldn't ever live there for shit; and I prefer Cleveland. But that being said, I'm not a millionaire 20-something basketball icon; although both Kyrie and myself love White girls with a booty, so, Boston does have that to offer I'm sure.
What I dislike is the fact that he felt it necessary to shit on Cleveland, rather than simply keeping the opinion to himself. An opinion that, I can understand, being that I've moved out of Cleveland and would not choose to return for reasons relating to "food," "culture," nightlife, etc... I get what he's saying -- but that doesn't mean it needed to be said.
It's just not the right time or place unless his specific goal was to put his name in the papers.