Let me start off by saying I believe Kyle Schwarber's second half breakout is real. He provides balance for the lineup as a second left-handed power source beyond Anthony Rizzo. While his defense remains a sore spot, you can continue to live with it while he produces offensively.
The question becomes, what does his production look like in the long-term? Does the defense continue to taper off as he ages and becomes less athletic? If so, the Cubs may not consider him a good candidate for a contract extension, in which case... does this mark the point in time for Schwarber's maximum trade value?
We all know what's coming after the 2021 season. Schwarber hits free agency along with Rizzo, Bryant and Baez. They won't pay them all. Indications are Javy is open to an extension and given his athleticism, is the best bet to age gracefully. Even if he doesn't stay at shortstop throughout the length of a long-term deal, he can always move to... well, anywhere else on the diamond, really.
That doesn't apply to Rizzo, or Schwarber. They already occupy corner positions, with Rizzo already limited to first base and Schwarber potentially forced to the same spot down the road. I'm inclined to let Schwarber play out this year then reassess next offseason. The team still needs to compete this year and will have a better idea of whether Schwarber's second half level is sustainable or not. They'll also have more information on any long-term concerns regarding Rizzo's back and what another extension for him will look like.
Jason Heyward is going to remain a Cub for a while in my opinion. He showed some life offensively last season we haven't seen during his Cubs career, but it is difficult to assess how much of it was the rabbit ball.
His defense appears to be in decline. Heyward is not a great fit in centerfield anymore, even if the Cubs can probably continue to get away with it another year. He should remain above average in right throughout the final four years of his deal, but I wouldn't expect any more gold gloves. At least not one based on merit.
Heyward is still a useful player and a team leader. The chances of the Cubs coming out ahead in a bad contract swap are minimal, or at least no better than the odds of Heyward improving his offensive output.
I add Kris Bryant here as we all know he is a capable corner outfielder who has spent time every season out there. He's coming off his worst year defensively at 3B, and there has always been long-term concerns regarding his ability to hold up at the hot corner. Injuries may be taking a toll. You just don't see many guys his height playing the position for a long time.
More playing time in the outfield could be beneficial. That is, if Bryant is still a Cub come April. As with Schwarber, if the Cubs are going to pull the trigger on a deal for one of their big name players, this is probably the optimal offseason to do it. If he sticks around, I would be open to playing Bryant more frequently in the outfield. Perhaps even in a platoon with Heyward, who should rarely start against left handed pitchers.
As with many of the Cubs bench players, Tony Kemp is more of a natural infielder, but his speed and versatility allow him to roam the outfield as needed. He hit a little better in September, but was still a major disappointment in the 2nd half after being acquired for Martin Maldonado. Kemp does offer contact ability and some speed this team desperately needs, but it remains to be seen what the Cubs plans are for him in 2020. He is out of options, which is the main reason he was available in trade last season. With the extra bench spot available on the expanded rosters next year, Kemp could prove valuable in a limited role, but it will require him to have a strong spring and he may end up in direct competition with a guy like Daniel Descalso for a job.
40-Man Roster Depth
Albert Almora (1 option year remaining), Ian Happ (2), Robel Garcia (2), Nico Hoerner (3)
Albert Almora is the only natural outfielder from this group but his nosedive at the plate over the last year and a half leaves his future in doubt. He is entering his first year of arbitration and his salary is estimated to end up around $1.8 million. That is a lot for a guy who has been one of the worst hitters in all of baseball since the 2018 All-Star break and who ended up back in the Minors in 2019. A change of scenery is probably in everyone's best interest, and if the Cubs don't assess much trade interest in him at that salary, they may have to consider simply non-tendering him next month.
It seems more likely at this point Ian Happ will be part of the Cubs 2020 roster than Almora. The two shared the centerfield job in 2018, and if both play to their potential could do so again, but I just can't see the Cubs standing pat at this position. Happ is the more versatile player, coming off a better season, even if he spent more of it in the Minors. Almora is the more accomplished defender, but Happ made strides in that area in 2019, and I no longer consider him a liability.
Ideally, neither enter 2020 as a starter. Nico Hoerner offers an additional intrigue at the position. There is no doubt Hoerner will spend plenty of time on the infield dirt, but the Cubs began exposing him to the outfield last year. In limited reps he performed well. He offers similar offensive upside as Almora, which is one more reason the Cubs could look to move Albert. Its possible Nico becomes the player the Cubs once envisioned Almora to be... with the ability to also play middle infield.
Robel Garcia was a fun story line in 2019. It is difficult to know what to expect moving forward. Was the power for real? Even if he proves it is, can he make enough contact? And even if he improves, is he a fit with the Cubs core? I don't project Garcia earning a bench role next spring, but if he shows improvement handling offspeed stuff in Iowa, he could work his way back into the 2B/LF rotation.
Mark Zagunis, Trent Giambrone, Donnie Dewees, Zach Davis
Mark Zagunis is a guy that falls a LITTLE short of being a big leaguer. On defense, he isn't quite athletic enough to handle centerfield. At the plate, he seems to forever be caught between having to sacrifice power for average or average for power. He's also been injury prone throughout his career. He's fine as a short term fill-in, but the boat seems to have sailed on him providing long-term value. The rest of the league seems to agree, as the 25-year old went unclaimed on waivers in the 2nd half of 2019.
And if it comes down to needing a fill-in, I do wonder if the Cubs wouldn't turn to one of their other options in Iowa. Trent Giambrone offers a better power/speed combo, and the ability to handle a couple of infield positions, while Dewees offers enough speed to run down balls in center, and make solid contact from the left side of the plate. Each has holes in their game (Giambrone's low contact/OBP, Dewees low power/OBP and weak arm), which is why the Cubs may still turn to the more experienced Zagunis, but the others offer more versatility in a bench role.
If any of the three are required for a large portion of the season it is likely a bad sign for the Cubs.
I include Zach Davis, not because he offers value in the long term, but because he is a plus runner and the best base stealer in the system. With the extra bench spot it is not out of the realm of possibility the Cubs look to utilize a speedster at times, just as they have with guys like Terrence Gore in the past. Davis isn't quite as fleet of foot as Gore, but he can match Quintyn Berry, Austin Jackson, Leonys Martin and others the Cubs have rolled out in limited roles. Over the past three seasons, Davis has swiped 102 bags while being caught 29 times (77.9% success rate).