David Kaplan said it best on the most recent CubsTalk Podcast:
"I think it's gonna be the most impactful offseason since Theo and Jed have been here."
He's not wrong, which is saying something given the Cubs have had plenty of impactful offseasons in the tenure of Theo Epstein and Jed Hoyer. This is a group that added Joe Maddon and Jon Lester ahead of the 2015 season and then the next winter, added Jason Heyward and surprised everybody by bringing back Dexter Fowler a couple days into 2016 spring training.
Anytime a team sets World Series or bust expectations and instead is going home just one day into the MLB postseason, change is coming. That may be especially true with HOW the Cubs got knocked out — leading the division and boasting the best record in the National League from the All-Star Break all the way through Game 162...yet they didn't even make it to the NLDS.
It's impossible to predict exactly what changes will be coming for the Cubs because as of this writing, three teams still remain and some of the winter's biggest names (Manny Machado, Clayton Kershaw, Craig Kimbrel) have yet to begin their offseason. There's still so much that can change even before free agency opens.
So if you're looking for a bunch of predictions or projections about what is going to happen in the Cubs world this winter, you're in the wrong spot. But here's where change MAY take place over the next couple months:
We'll start with the area that will probably have a resolution the soonest. Teams typically prefer to have their coaching staff settled as early as possible into the offseason so they can fill out the roster from there. An added bonus is the new coaches can start reaching out to players on the roster earlier in the offseason if they choose to, as well.
With the Cubs coaching staff, there very well may be more shakeup coming this fall even after Chili Davis was let go last week. All we know for certain is Anthony Iapoce will be the team's new hitting coach in 2019 on Joe Maddon's staff. Beyond that, the Cubs have not publicly confirmed that Jim Hickey or any the other coaches will 100 percent be back next spring.
There's a potential the Cubs' 2019 Opening Day lineup will be far different from not only the 2018 Opening Day lineup, but also even the NL Wild-Card lineup.
Like their fans, the Cubs were unhappy with the way the offense performed in the second half, particularly in three of the final four games (the penultimate regular season contest, Game 163 and the Wild-Card game).
So much has been made of the Cubs' young core of position players over the last few years, but the evaluation has to change after a bunch of the members of "The Core" took steps back in 2018 (Willson Contreras, Addison Russell, Ian Happ, Albert Almora Jr.).
Kyle Schwarber enjoyed a bit of a resurgent season as he cut down on strikeouts, walked more and boosted his batting average while improving as a defender, but also saw a dip in power and still hasn't taken that big step forward toward one of the league's most feared run producers.
Kris Bryant also obviously experienced a dip in offensive production, but so much of that can be tied into the left shoulder injury that clearly affected his swing.
After a disappointing end to the season that highlighted the offensive shortcomings, Epstein was blatantly honest about how the evaluation of these players has to evolve:
"It has to be more about production than talent going forward," Epstein said. "And that includes our own assessments. Beyond that, it's also trying to understand why we're not where we should be with some individual players. In other words: If you look back, players who do certain things at 22 and 23 should be progressing into a better, more productive phase of their career at 24, 25 and 26.
"I'm the first one to talk about how development and progress — those aren't linear things all the time. There are a lot of ups and downs. But I think there's a trend where Javy took the big step forward, but there are other guys who went the opposite direction or have been trending the opposite direction a little bit. We have to get to the bottom of that.
"It's our job not just to assemble a talented group, but unearth that talent and have it manifest on the field. Because that's ultimately all that matters. It's an assessment on those two fronts. The talent that we have and who's going to be productive, who's not or where we can find that production. And then also understand the environment and are we doing everything that we can in creating just the right situation to get the most out of these guys."
And therein lies a perfect transition into the next category...
With that aforementioned core of young position players, the only former members of "The Core" that have been traded away are Jorge Soler and Starlin Castro. Year after year of trade rumors and yet as of this writing, guys like Schwarber and Russell and Happ remain in Cubs uniforms.
Will that change this winter? Obviously we don't know for sure, but it seems as likely as at any other point in the last few offseasons.
Reading the tea leaves, it would make sense for the Cubs to deal away at least one of those core members this winter to either bolster the bullpen or restock the farm system.
For starters, the offensive dip in the second half could portend the need for change. It's very hard for a big group of young hitters to all develop on the same path at the same pace, which means the learning curve can lead to prolonged slumps that occur all at the same time — which we've seen often the last few seasons.
Epstein was also candid about how the players aren't quite as happy with Maddon's ever-changing lineup as they once were which also means the Cubs probably have to shed some of their depth at some point if they truly want more stable playing time. Almora or Happ can't sit on the bench five times a week without completely inhibiting their development path.
The Cubs also showed exactly how they feel about this group of hitters when they went out and acquired Daniel Murphy in August, stressing the need for his "professional at-bats" in the lineup on a consistent basis at the most important time of the season.
The Cubs will have World Series expectations in 2019, so once again, they figure to be big players in free agency. Even if they don't wind up with Bryce Harper or Manny Machado, they will at least kick the tires on the two superstars since they're clearly in the market for improved offense.
But beyond the big fish, the Cubs need to add to the bullpen, bolster the lineup, acquire some more shortstop depth and potentially even add a veteran backup catcher to help give Contreras more regular rest. All those moves could come from the free agent market.
Will he be back? Even if he is still on the Cubs roster at the start of next year, would he make it through the year? The Cubs may eventually trade him, but why give up on him at a time when Epstein said it's important for the organization to support Russell and his value is also the lowest it's ever been? Strictly thinking in a baseball sense, he could be a perfect midseason trade piece.
Regardless of what happens with Russell, there is some change for the Cubs in that for the first time ever, Javy Baez will enter the official offseason as the clear starter at shortstop next year (at least for the first month).
Whoever the Cubs add this offseason to help the lineup and subtract from the roster that ended 2018 will still have to fit in the same defensive puzzle somehow. For example, if the Cubs signed Machado, they could slot him in at shortstop a bunch, which opens up Baez to float and play second a bunch or third, which moves Bryant to the outfield, which moves Schwarber to the bench. And on and on with any potential move the Cubs make this winter.
On the other hand, taking guys away from the current defensive puzzle also would have ripples throughout the rest of the roster. For example, if Happ is traded away, that also removes a switch-hitter and a guy with a ton of defensive versatility away from the roster. What does that do to the depth chart in the outfield or at third base?
There might not be any change in terms of additions to the Cubs' rotation ahead of 2019, but that's not to say there won't be any movin' and shakin'.
Assuming the Cubs pick up Cole Hamels' $20 million option — which they should and probably will — that will leave them with Jon Lester, Kyle Hendricks, Hamels, Jose Quintana, Yu Darvish, Tyler Chatwood, Drew Smyly and Mike Montgomery all under contract for next season and all projected to be healthy enough to pitch by the start of spring training. (Before you ask: yes, the Cubs are planning on Smyly as a starter right now; Epstein said as much in September.)
Lester, Hendricks and Quintana are locks for the Opening Day rotation, as is Hamels if that option is picked up. Darvish will surely be in the rotation, too, assuming he's fully over the elbow/triceps issue that limited him to only 40 innings in his first year in Chicago.
So what will the Cubs do with Smyly, Chatwood and Montgomery? Smyly will be on an innings limit in 2019 after missing the last two years due to Tommy John, so it's possible the Cubs opt to switch gears and just throw him in the bullpen to start the year. They may do the same with Montgomery, but will the veteran lefty be OK with that after publicly admitting he wants to start at various points over the last year-plus? Would Chatwood be OK in moving to the bullpen or would the Cubs just move him if he is still having command woes?
Epstein and Hoyer often remind you can never have too much pitching, but in a way, the Cubs may have too much starting pitching on their roster for 2019 taking up a big part of the team's payroll. Is it possible we'd see a guy get moved this winter as a result? You never know.
This is the most mundane area, as every team makes pretty significant changes on their 40-man roster each offseason — even under the radar. There will always be shakeups with players getting DFA'd to create room for new additions, prospects added to the 40-man roster so as to be protected from the Rule 5 Draft, etc.