Maybe we have difference of perspective with this upcoming season. As soon as they non-tendered Schwarber and traded Darvish that was the white flag that they were in sell off mode and I think they will be between now and the deadline. The core of this roster has underachieved for multiple years now that either you go all in and add some expensive pieces to compete or you start the rebuild process and I have accepted that they are in rebuild mode now and have little to no attachment to any players left except maybe Rizzo, Javy, and Hendricks and even then I am starting to wonder what their futures are if the right deal comes along.
The NL Central is garbage this year so I find no joy in winning the division with 85-90 wins then getting pounded by the Dodgers or Padres in the first round. Holding onto KB is stupid at this point, he is not going to re-sign with the Cubs unless it is a ridiculous deal and the Cubs have made it pretty clear by now they aren't going to do that. They missed the boat on trading him and Schwarber before last season when they had some value, now they are hoping KB starts off hot and stays healthy that they can get a decent prospect back I guess. I am OK with trading Contreras for a good return if they can get it because by the time this team is any good again he probably will be too expensive to keep around. I love his arm and bat when he is at his best but he has been terribly inconsistent so why waste his best years on a losing team when he probably can get them the best return on a trade.
The window is closed, even best case scenario with this current roster all the cheap reclamation signings they made have good years and they are in the hunt for the division at the deadline but history usually proves those hot starts fizzle out and they return to earth or get hurt and this team limps into the playoffs and gets swept by a superior team. I would rather trade off whatever valuable assets they have for best returns and suck for 2 or 3 years while the talent they get back develops in the minors than to let this core walk for nothing and suck for over 5 years until they rebuild through the draft which they don't have a good track record of doing.