Adrian Chen. No contest. There have been some winners and some losers who have come and gone in the past, but for my money, nobody has been so consistently crap as Chen. He's becoming the unfunny Tim Meadows of Gawker.
ETA: Please note, I have absolutely no evidence with which to support this claim. I was just reading his most recent post about Lindsay Mills, and I came to the realization that I can't remember a single Adrian post that I've ever enjoyed. Purely subjective shade throwing here.