They had similar, if not the same, needs last off-season. Jed didn't fix it then and I have no reason to believe that he is capable.
I'm sure that they would love to win during negotiations with Comcast but that isn't going to happen. If they didn't want a winning team to show off for negotiations, I doubt that they would field a winning team for any reason other than dumb luck. They didn't fix anything even with that over their heads.
The stands are full. Cup snek will manifest. People frequent the Ricketts neighborhood businesses regardless. They don't care. They're very lucky that their competition for market share at this time of year is the White Sox. They're still making money on what Harry Caray was selling. They'll continue to pick up guys from the scrap heap and try to flip them at the deadline because they see themselves as the smartest people in the room.