Chicago Cubs: Here’s my personal wish list for the team this winter

The Chicago Cubs are facing an uncertain offseason. What will the club look like under new manager David Ross? Here’s one opinion on what should happen.

After winning the World Series in 2016, it’s been three straight years of regression for the Chicago Cubs. In 2017, they lost in the National League Championship Series and in 2018 they lost in the NL Wild Card Game. Then this season, inconsistency plagued this team before a nine-game losing streak in September knocked them out of the playoff race, leading to a disappointing 84-78 record.

As such, the team is facing both its most important and its most uncertain offseason in years. The pitching certainly needs to be addressed, while on offense second base and center field were problems last year. In addition, the front office faces several tough decisions on whether to bring players back next year.

In a perfect world, we’d re-sign Nicholas Castellanos, trade for Mookie Betts and sign Gerrit Cole and Anthony Rendon… but that’s not all going to happen. We have to be realistic. To that end, I’ve tried to put together a realistic plan that will improve this team enough to be a serious contender in the National League Central in 2020.

Chicago Cubs: Some pieces are needed on offense

The biggest question that Chicago Cubs fans are asking heading into this offseason is, “Will the team re-sign Nicholas Castellanos?” Castellanos had a monster final two months of the season after coming over in a trade from the Detroit Tigers, which caused fans to want to bring him back but simultaneously drove up his value. With Scott Boras as his agent, bringing back Castellanos is not going to be easy.

Still, the Cubs need to figure out a way to make it happen. Not only is Castellanos one of the most productive hitters on the market, but he also proved that he is a good fit at Wrigley Field. Castellanos could continue to play right field every day, moving Jason Heyward to center.

The Cubs have a decision to make on Albert Almora, Jr. There’s been talk of non-tendering him after a rough year, but especially given how cheap he will come, I think it’s too soon to give up on him. Still, the team could use another outfielder, and there aren’t many free agent options available. I would see if the team could sign Brett Gardner, though there’s a good chance he’ll want to stay with the Yankees. He’s coming off one of his best seasons, setting career highs in home runs, RBIs, and OPS, and he would provide a veteran presence while having the ability to play center and left field.

Looking at other positions, assuming the Cubs don’t trade away any of their big pieces, they should be set at every other position except second base. A lot of fans want Nico Hoerner to be the second baseman next year, but his excellent showing with the big league club late in the year was too small of a sample size to assume he’s ready to play there full-time. It would be wise to bring in a veteran to help stabilize the position.

Howie Kendrick seems to be a great fit. He’s a career .294 hitter who batted a career-high .344 with a solid .966 OPS in 2019. This year, he’s played first, second, and third base, so the Cubs could move him around. Regardless of how Hoerner plays out, Kendrick should still get plenty of playing time. Being 36, it wouldn’t take a long-term deal to sign him.

The other big decision is whether to non-tender Addison Russell. I think most of us are in agreement that he will not be back. (I’m also not counting on Ben Zobrist being back, as we don’t know yet whether he will retire.)

Chicago Cubs: A final look at the roster

Notice that I didn’t mention trading Kris Bryant, Javier Baez, or Willson Contreras, as some fans have speculated the Cubs might do this offseason. Despite coming off a disappointing year, this is not a situation where the team has to completely start over. It’s hard to envision a trade involving these players that would significantly upgrade the overall roster for 2020. So, even though they may risk losing Bryant especially to free agency, I would hold onto them.

So, if the Cubs were to make all the moves that are described above, this is what the roster would look like in 2020:

Starters:

C Willson Contreras

1B Anthony Rizzo

2B Howie Kendrick

SS Javier Baez

3B Kris Bryant

RF Nicholas Castellanos

CF Jason Heyward

LF Kyle Schwarber

Bench:

C Victor Caratini

IF David Bote

IF Daniel Descalso/Tony Kemp

IF Nico Hoerner

OF Albert Almora, Jr.

OF Brett Gardner

Starting Rotation:

SP Jon Lester

SP Yu Darvish

SP Kyle Hendricks

SP Madison Bumgarner

SP Tyler Chatwood/Alec Mills

Bullpen:

CL Craig Kimbrel

RP Pedro Strop

RP Bradon Kintzler/Steve Cishek

RP Kyle Ryan

RP Tyler Chatwood/Alec Mills

RP Rowan Wick

RP David Phelps

(RPs Brad Wieck, Adbert Alzolay, and Duane Underwood, Jr. are also options.)

I understand that there are still a lot of question marks on this team. Will Kimbrel return to form? Are Ryan and Wick the real deal? Can Lester bounce back? Will Heyward continue to show improvement? Has Schwarber finally turned a corner? And above all, will the team play with a renewed sense of urgency under David Ross? That last one is the biggest wild card in all this. A lot of things would have to go right for this roster to contend in 2020, but that’s the case with every big league club.

I also understand that it’s not likely that the Cubs will make all these moves. And I know many fans have a much different vision for this team in 2020. This is just my best-case scenario while also trying to be realistic. If I were in the Cubs’ front office, these would be my priorities this offseason. Regardless of what happens, we figure to see plenty of change, and I do believe this front office is going to make a strong effort to put together a winning Chicago Cubs team for 2020.