While Winer certainly deserves respect for all he's done, that Twitter squabble with Arrington et al. certainly didn't help his public image. Arrington has a well-established reputation as a master troll, and it was rather sad to see Winer take Arrington's bait hook, line, and sinker.
His near-absolute disinterest in visual design, his chronically caustic personality and his apparently principle-driven burning of bridges haven't helped either.
Ouch.
Other applications have tried to address this already. An example I can think of on the top of my head is Hellotxt, but I'm sure there are others.