To be fair: Before there was Olberman, there was Lupica. You are correct that he has been losing his following as a sports columnist, because it's clear that he doesn't watch a lot of sports anymore. When he watched every Yankees game and talked to the players all the time, it was clear that he had access to information you didn't have, so he was still interesting. These days, I bet he hasn't watched an inning of spring training, and it makes you realize that he grew up a Red Sox fan in New Hampshire. That's why he lives in New Caanan: Greenwich and Stamford kids grow up Yankees fans. New Caanan is on the front line of Red Sox Nation.
Damn! I spent 10 years in Norwalk, and don't recall more than a handful of non-Yankee fans in the whole of Fairfield County, and most of those were Mets fans. Red Sox fans down there? I thought when I moved out, membership in Red Sox Nation in the area was cut by about 50%