Cubs 2020-21 Offseason Plan Project: Join the Conversation

With the 2020 MLB World Series getting underway this evening between the Tampa Bay Rays and the Los Angeles Dodgers, it’s time to begin working on plans for the 2020-21 offseason, and we’re inviting you to share your thoughts and plans with us and the rest of the fanbase.

All you have to do is use the template below (copy/paste) and begin to lay the foundation for what you believe will be the path to success for the 2021 Chicago Cubs!

When completed, save your plan as a PDF and send it to for it to be published on the website.

Note: We will not include submissions with vulgar or explicit language, so let’s keep it clean.


In the introduction section of your off-season plan, you’ll talk about where you see the Cubs heading into the 2020-21 offseason, your outlook and philosophy on what they need to accomplish this winter, and explain the thinking/strategy behind your offseason plan.

Arbitration-Eligible Players

For this portion of the offseason plan you will be deciding whether to “tender,” or “non-tender” the listed arbitration eligible players for this year.

If you would like to think even more outside the box, you can opt to extend an arbitration-eligible player such as Javier Baez, for example. Remember, this is your plan, and the level of creativity/complexity is purely up to you.

We have listed the arbitration-eligible players and their projected 2021 salary according to MLB Trade Rumors’ first model for 2021 arbitration salaries.

  • Albert Almora Jr. – $1.575M:
  • Javier Baez – $10.0M:
  • Kris Bryant – $18.6M:
  • Victor Caratani – $1.2M:
  • Willson Contreras – $5.0M:
  • Ian Happ – $2.5M:
  • Colin Rea – $1.0M:
  • Kyle Ryan – $1.2M:
  • Kyle Schwarber – $7.01M:
  • Ryan Tepera – $1.2M:
  • Dan Winkler – $1.0M:
  • Jose Martinez – $2.1M:

Club Options

This section is a quickie within the exercise where you will simply decide to “pick up,” “decline,” or “rework” a player’s club option for the 2021 season. You’re welcome to provide as much, or as little explanation as you’d like on your decisions.

  • Jon Lester –  $25M ($10M buyout)
  • Anthony Rizzo – $16.5M ($2M buyout)
  • Daniel Descalso –  $3.5M ($1M buyout)

Impending Free Agents

The Cubs have several impending free-agents heading into this offseason, and it’s your job to decide whether to allow each player to walk or work out a new deal.

You should explain your decision and the reasoning behind that decision.

  • Jose Quintana (SP): ($10.5M in 2020)
  • Tyler Chatwood (SP): ($13M in 2020)
  • Andrew Chafin (RP): ($3.04M in 2020)
  • Pedro Strop (RP): ($1.82M in 2020)
  • Cameron Maybin (OF): ($1.5M in 2020)
  • Jeremy Jeffress (RP): ($850K in 2020)
  • Jason Kipnis (2B): ($1M in 2020)
  • Billy Hamilton (OF): ($1M in 2020)
  • Josh Phegley (C): ($1M in 2020)

Manager/Coaching Staff

With the potential firing of Anthony Iapoce as Hitting Coach, the Cubs may have one replacement this offseason. While the rest of the staff seems safe/set, this is your offseason plan, and with that you can feel free to make any changes you wish. Again, elaborate on decisions you make.

Manager: David Ross

Bench Coach: Andy Green

Pitching Coach: Tommy Hottovy

Hitting Coach: Anthony Iapoce

Free Agency Acquisitions

Here’s where the real fun begins. List your free-agent signings and your reasoning for the move in this section of the exercise. Use the format below and elaborate on the move. Spotrac is a great place to see impending free-agents and their projected salaries, but you can pull this information from any place you choose, so long as you cite the source of that information.


  • Marcus Stroman (SP) – 5 years, $80 million: Per Spotrac, Stroman was set to make $12 million in 2020 before opting out. One would imagine he receives a raise from that AAV as one of the top SP’s available, and entering his age 30 season, a multi-year deal is a logical outcome.


Here you can make the Winter Meetings blockbuster that you’ve always dreamed of, but we suggest something reasonable for both sides involved. Let’s hope you have better luck than Theo Epstein and Jed Hoyer did last offseason when they were heavily involved in discussions that never came to fruition.


Player X (Cubs) for Player Y (Trade Partner): To the left in bold you’ll list the player(s) involved in the swap as well as their team, followed by an explanation of the trade and why it makes sense for both sides involved.

Winter Wrap-up

In this final leg of the exercise you’ll summarize your offseason moves and the strategy/logic behind them.

If you choose, you can list a projected 26-man roster based on your acquisitions and departures within your offseason plan. This is highly encouraged, but not required.


Position Players




Starting Rotation:


REMEMBER: When you’ve completed your plan you need to include your plan in an email as a PDF and send it to for it to be published on the website!

Featured Photo: Jon Durr, Getty Images


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