A Washington Post scribe before he made the leap to TV news—dig the non-telegenic mustache and eyewear in the author photograph for Dream City, his book on Marion Barry—Sherwood has been covering District politics since Barry was still mayor-for-life. The seasoning has provided him with a posse of sources that usually put him ahead of the pack on the latest Wilson Building gossip.
But what elevates Sherwood above even his fellow all-star District media scoopsters is his sense of humor. Sherwood mocks District’s pols both behind their backs and to their faces. Last year, at a roast for Ward 2 councilmember Jack Evans, Sherwood’s shtick included removing a phony “wire” from his person, saying the gag was no good since Mayor Vince Gray hadn’t made it. He’s even more useful when the mayor is on hand: Gray’s regular news conferences, with their announcements of minor governmental initiatives and obscure new appointees, would be eye-jabbingly dull were it not for Sherwood’s injection of wit.
And amazingly, that dry humor hasn’t come with a cost: Most pols love Sherwood, no matter how much he makes fun of them.