Bold predictions for the Cubs' 2019-20 offseason

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The Cubs are just a couple of weeks away from a pivotal offseason that could see a lot of change coming to Chicago's North Side.

Then again, we thought the same thing a year ago and it turned out Theo Epstein's biggest move last winter was signing Daniel Descalso to a two-year deal.

But after missing the playoffs in 2019, the Cubs are now at a crossroads as an organization. 

The NBC Sports Chicago crew previewed the offseason on the latest CubsTalk Podcast with some bold predictions for the winter.

Listen here and check out the fearless calls below:

(Note: Rationale and more context on each bold prediction in the podcast.)

David Kaplan

1. Cubs are going to take a page out of the Yankees' book and retool on the fly rather than go all-in to contend in 2020.
2. Jose Quintana has thrown his last pitch as a Cub.
3. This will be the second-to-last offseason for Theo Epstein as the Cubs president of baseball operations.

Kelly Crull 

1. Cubs re-sign Nick Castellanos and trade away Kyle Schwarber.
2. Tyler Chatwood will be in the 2020 rotation.
3. John Lackey will be named quality assurance coach on David Ross's coaching staff. (Kidding, but only kind of...)

Tony Andracki

1. Before the Cubs play a Spring Training game, Javy Baez will sign an extension that will keep him in Chicago through at least 2023.
2. Willson Contreras will be traded this winter and the Cubs will get some much-needed pitching help in return.
3. Cubs sign Howie Kendrick this winter as the professional bat and lefty-masher they craved in 2019.
4. Ben Zobrist will return on a one-year deal and finish his playing career in a Cubs uniform.
5. David Bote, Albert Almora Jr. and Addison Russell will all be traded or non-tendered this winter as the Cubs remake their bench/depth.

Jeff Nelson

1. Willson Contreras will sign a contract extension.
2. Ben Zobrist will return as a player/coach.
3. Jose Quintana will be traded for minor league depth.
4. Terrance Gore will be signed to be the 26th man on the roster under the new rules.

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