The Cubs are listed prominently among a group of 13 teams that could define the offseason, though the same things thought to spur their aggressiveness could also be seen as reasons to temper expectations. Hiring Craig Counsell was an incredible coup that signals a desire to go all-in on the offseason, but it might instead mean they expect to win with smaller budgets like Milwaukee did. Losing Brandon Woodruff and reportedly being willing to trade everyone opens the division up for the Cubs, though an easier path won’t take as much work to follow.