2 to keep, 2 to trade - 3. Tyson Miller (Keep)
This argument can go either way; Tyson Miller has been solid since being picked up off waivers by the Cubs in May. Given that he is still in his pre-arbitration phase, he is one player who can fetch a decent prospect at the deadline. However, since he has that team control for the next few years and the Cubs need for bullpen efficiency that the Cubs already display night in and night out, the team must keep its productive, controllable arms in the pen intact as much as possible.
The team will have to add bullpen arms in free agency this winter. This cannot go on where the Cubs have a gaping hole in an area of their roster, so moving the arms that actually can put up solid numbers out of the pen for cheap is extremely counter-productive as, again, the team isn't looking to enter a full-scale rebuild. Keeping the cost-effective pieces that can produce is a must for the Cubs at this juncture.