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

(Photo by David Banks/Getty Images)
(Photo by David Banks/Getty Images) /
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Chicago Cubs
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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:


C Willson Contreras

1B Anthony Rizzo

2B Howie Kendrick

SS Javier Baez

3B Kris Bryant

RF Nicholas Castellanos

CF Jason Heyward

LF Kyle Schwarber


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


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.

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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.