Be sure to take a look at Dan Kennedy's deconstruction of today's Howie Carr column. As Dan notes, Carr's blue-collar wrath--which may have been appropriate back when when he was a Deerfield Academy student and his father was a Deerfield stockroom worker, but makes less sense now that he's a high-earning pundit living large in Wellesley--leads him to totally mischaracterize the background of Boston Newspaper Guild head Dan Totten, whose humble roots actually resemble Carr's own.
I'm not entirely unsympathetic to Carr: I went to a private school where a lot of kids came from pretty affluent families, and my memory of that disparity is still remarkably fresh. That said, does Carr still need to be working through his economic baggage in the pages of the Herald? Or telling his radio audience that he got into Brown (really!), but didn't have enough money to go?
Whether or not you like Carr's politics, and I generally don't, he's a talented entertainer with an unparalleled knowledge of Massachusetts politics. The angry-proletarian shtick might delight some of his hard-core fans, but it also makes him look absurd. Whatever happened back then, it's time to move on.