2 players the Chicago Cubs should keep and 2 they should trade

2 to keep, 2 to trade - 2. Drew Smyly (trade)

Drew Smyly is in a walk season and has had a good enough year to help a competing team. That alone is enough to warrant the Cubs moving him and at least getting something so he doesn't walk for free. Most teams could use a southpaw out of the bullpen who can fill in as a spot starter, so the Cubs certainly have a decent enough trade chip. Moving him also frees up his roster spot for a prospect to move in, as it seems we will have youth development in the second half.

You also need that roster spot to be filled by players with minor league options so you can rotate as necessary, and therefore, keeping Smyly on this roster does nothing to help the Cubs if they are throwing in the towel. Expect him to be moved at the deadline.