The Cubs find themselves in the same position as they did last off-season.
The Cubs are in need of the following:
1. TWO STARTING PITCHERS. Darvish and Chatwood signings were a total disaster. Darvish has an arm injury and Chatwood is a walk machine. Darvish injury is a stress reaction which is a precursor to a stress fracture in his elbow. It was reported that 8 weeks of rest would be the treatment plan, but one has to put a question mark on whether the injury is problematic (due to mechanic's etc). Chatwood may get a second chance, but most believe he can maybe salvageable as a long reliever. Montgomery was the 6th starter for most of the year. In 19 starts, he went 5-6, 3.99 ERA and 1.1 WAR. That may not be enough to claim the 5th starter role in 2019. The Cubs have to prepare to sign two more starting pitchers this off-season (Smyly does not count since he did not recover from his injury in the projected time frame to help the club in 2018).
2. LEAD OFF HITTER. Ever since Dexter Fowler left for free agency, the Cubs have not had a consistent lead off hitter (even though Fowler was not the prototypical lead off batter). It was recently reported that not all Cub players are happy with Maddon's new line-up everyday philosophy. Players want an established lineup order to better prepare for their games. The idea of leading off Rizzo, Bryant, or Baez (usually to get them out of slumps) hurt the run producing slots down the line. The Cubs had a major issue in run scoring. It was feast or famine. The second half was a painful drought. In 40 games, the Cubs scored less than 3 runs. The Cubs could not manufacture a run with a walk, stolen base and a single (only when pinch runner Gore made the club was there a slight glimmer of old school baseball.) When the hitting philosophy changed from launch angle/home run upper cuts to level line drive/opposite field for average, the Cubs offense was more ineffective. Having a high OBP, contact hitter with stolen base speed at the top of the order allows the Cubs the ability to manufacture at least a run every three times through the order. But advanced statistics (which Theo seems to be addicted to) calls out base steals as being counter-productive (risk-reward).
3. CLOSER. Morrow signing was hailed as a good move, but risky. He had a history of arm issues. But the front office said that the team would not "overuse" him. But Maddon, who really has a problem managing his bullpens, used Morrow three games in a row (for no apparent reason) which led to Theo believing that ended Morrow's season. The alternative closers did not step up to replace Morrow. Edwards seems to lose concentration in high leverage situations. Strop can be good, but Maddon making him bat after throwing 1 2/3 innings which led to his hamstring injury killed the final run. Cishek was overused by Maddon throughout the season so that his throwing arm is a foot longer than normal. There is no dominant arm in AAA to be the next closer. It is hard to trust whether Morrow will come back fully healthy, or whether he can be the regular closer in 2019.
The front office was under orders to not go over the luxury tax threshold in 2018. They bumped up to the ceiling by the end of the year. There is not much coming off the payroll for 2019. With arbitration players and existing contracts, the Cubs project to be near the $200 million mark, only $6 million from the new tax cap. If Russell is given his walking papers or traded, that saves around $3 million. A $9 million window will not sign a big FA like Harper, or exercise the $20 million option for Hamels.
You have to realize that there is still tension between baseball operations and the "business" side of the Cubs. Ricketts and Kenney were budgeting and banking on the Cubs going deep in the playoffs. The was the expectation from fans and ownership. If the Cubs would have gotten to the NLCS, the team could have banked at least $60 million in premium post-season revenue. That has to be a sore spot for the bean counters and the huge investment Ricketts has made outside the ball park. There is no reason to expect the Cubs to spend like drunken sailors this off-season to get an ace pitcher and a big expensive bat after spending $186 million on Darvish, Chatwood and Morrow who are under contract.
When Theo said in his state of the Cubs post-season press conference that they would be not looking at "talent" but "performance," he was calling out his young core guys: Schwarber, Happ, Contreras, Almora. Theo has a track record of loving his guys to the point of over-valuing them (and not trading them when they had value). Some reporters believe after the flat finish to the season, no one is untradeable from the roster. But the front office and scouts may still have rose color glasses on their players "turning things around." The roster is filled with .230 hitting platoon players. It would be rare for all of them at the same time to have sudden career years in 2019. Spring training needs to be a battle for starting positions. Give the position to the player who earns it, so he can be hungry enough during the season to perform to keep it. That level of internal competition has been missing in the clubhouse under Maddon because juggles the lineup so everybody plays. But that track may not help in the development of players. Likewise, giving the job to a player on the up-cycle (like Contreras at catcher) does not necessarily guarantee continued success (at least offensively).
In one respect, the Cubs 2019 roster is pretty much hand cuffed by the underperforming core of young players. The Cubs championship window is now (and closing fast). The win-now demands means that they cannot shop for prospects and wait three years to promote them to the major league team. Do you blow up the team and trade for veterans on the downhill side of their careers for one last death march to the pennant? Of do you stay the choppy course with the guys you have?