Cubs 2020-21 Offseason Plan Project: Austin Bloomberg’s Offseason Plan

Continuing with The Dugout’s Offseason Plan project, I am offering the first iteration of an offseason plan from the Cubs perspective. Over the coming days you will see additional plans from more of our contributors, for both the Northside as well as the Southside.

(Curious about what our Southside writers think? You can check out Patrick Flowers’ White Sox plan here, along with our first reader submission for the Sox from Plainfield Matt.)

If you wish to contribute a plan of your own, click here for the template. 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.


After winning the NL Central in an awkward, 60-game season, the Cubs quickly bowed out of the playoffs — suffering a sweep in the Wildcard Round at the hands of the upstart Marlins.

The Cubs of 2020 were quite similar to the teams of 2018 and 2019. After much talk about this team having a ‘reckoning’, what we’ve witnessed is much of the same. There’s been little roster reconstruction, and while we’ve seen changes to the coaching staff over the years, along with a firming up of the team’s player development and infrastructure, the continued use of the same players while hoping for change hasn’t gone well.

I’m going to be realistic for the Cubs with my offseason plan. I don’t envision a payroll that approaches the Luxury Tax — and my final payroll (below) is probably far too generous. I’ve also recently written that it’s impossible to predict what the Cubs will do this offseason, yet this is a fun exercise, so here I am.

With a limited budget, life in the midst of a pandemic, and several players due for arbitration raises, it’s hard to envision that ‘reckoning’ ever becoming a reality until after 2021. The Cubs are at a significant crossroads, and it’s difficult to envision how they might walk that fine-line between remaining contenders while re-tooling for the future.

Given those parameters here’s what I’d do to give the Cubs the best shot of winning in 2021 while keeping the future promising.

Arbitration-Eligible Players

Albert Almora Jr. – $1.575M: Non-tender

Javier Baez – $10.0M: Extend (7 years, $125 million)

Kris Bryant – $18.6M: Tender

Victor Caratini – $1.2M: Tender

Willson Contreras – $5.0M: Tender

Ian Happ – $2.5M: Extend (5 years, $50 million)

Colin Rea – $1.0M: Non-tender

Kyle Ryan – $1.2M: Tender

Kyle Schwarber – $7.01M: Tender (then trade)

Ryan Tepera – $1.2M: Tender

Dan Winkler – $1.0M: Non-tender

Jose Martinez – $2.1M: Non-tender

A couple of decisions clearly stand-out here. Perhaps the biggest surprise is that I would trade Schwarber, who is coming off a disappointing 2020 campaign (.188/.308/.393) and has been entirely inconsistent with the Cubs. In a contract year, now is finally the time to extract whatever value the organization can. Schwarbs is estimated to make anywhere from $7-$9 million in his final year of arbitration, after which he’ll certainly enter the open market. The Cubs could net a couple of lottery ticket arms in return (more on that later).

Conversely, I’d utilize a down year from Baez to lock him up on that long-awaited extension. He wants to stay in Chicago, and a $17.85M AAV is more than reasonable given his track record, defensive wizadry, and overall value to the organization. The deal would keep Javy locked up through his age-34 season.

Continuing with extensions, locking up Happ now as opposed to later seems like a worthwhile endeavor. Sure, other players (Contreras) will hit free agency sooner, but Ian had a breakout campaign and he’ll only get more expensive as he continues through arbitration. A $10M AAV for five years wouldn’t break the bank, buying out his arbitration years plus two additional seasons, carrying him through his age-30 season. This would be a prudent move, offering Happ a raise now with a chance for a big payday on the open market in five years.

Other than those three, my decisions are self-evident. Most notably, the Cubs hope that health, a contract year, and a chip on his shoulder motivates KB to return to MVP form — and I’m willing to bet that becomes reality.

Club Options

Jon Lester –  $25M ($10M buyout): Decline, Re-Sign (1 year, $7M; Club Option for 1 year, $10M, $2.5M buyout)
It’s clear the Cubs aren’t going to exercise Lester’s option for $25M. Entering his age-37 season season in 2021, his numbers in 2020 — despite a promising start — were a disappointment. That said, his veteran presence, meaning to this organization, and ability to still provide value as a No. 5 offer the Cubs an opportunity to re-sign him on the cheap. The $10M buyout does not count against 2021’s Luxury Tax, making a cheap re-signing all-the-more likely.

Anthony Rizzo $16.5M ($2M buyout): Pick Up
This is a no-brainer. While the Cubs would be wise to seek another extension with Rizzo, that I have them already extending Baez and Happ leaves Rizzo playing on the Northside in a contract year before getting an extension after the ’21 season.

Daniel Descalso –  $3.5M ($1M buyout): Decline
Descalso hit .173/.271/.250 in 2019, and saw zero action in 2020. This is an easy decision, and entering his age 34 season, Daniel will be seeking a MiLB contract elsewhere.

Impending Free Agents

Jose Quintana (SP): ($10.5M in 2020): (Walk)

Tyler Chatwood (SP): ($13M in 2020): (Walk)

Andrew Chafin (RP): ($3.04M in 2020): (Walk)

Pedro Strop (RP): ($1.82M in 2020): (Walk)

Cameron Maybin (OF): ($1.5M in 2020): (Re-Sign) (1 year, $2M; Club Option for $3M, $500K buyout)

Jeremy Jeffress (RP): ($850K in 2020): (Re-Sign) (2 year, $6M)

Jason Kipnis (2B): ($1M in 2020): (Re-Sign) (1 year, $2M)

Billy Hamilton (OF): ($1M in 2020): (Re-Sign) (1 year, $1.5M)

Josh Phegley (C): ($1M in 2020): (Walk)

Not much surprise here. Jeffress was fantastic with the Cubs in 2020, yet his peripherals (4.09 FIP, 13.6 BB percentage), previous injury history, and age (33) aren’t conducive to a lucrative contract at a notoriously volatile position. The Cubs re-signing him to a modest, multi-year deal seems both logical and within reach.

Maybin was a nice piece for the Cubs in his September cameo. 34 next year, Cam can play all three outfield positions with aplomb, still has above-average speed, and knows how to play a bench/veteran role. A one year deal with a club option is certainly attainable, and he’d nestle into the fourth outfielder role.

Kipnis returns on a modest, one year deal to serve as Nico’s back-up and insurance policy, while the Cubs re-sign Hamilton for a veteran speedster off the bench as the DH disappears in 2021.

Manager/Coaching Staff

With Anthony Iapoce expected to return as Hitting Coach after recent rumblings he was on the hot seat, the Cubs’ quartet of manager and top coaches appears set. Third Base Coach Will Venable may get a shot to manage the Detroit Tigers, however, and Terrmel Sledge was recently dismissed, so there’s a changing course for the Cubs ancillary coaching staff. That said, 2021’s coaching staff will remain consistent at the top:

Manager: David Ross

Bench Coach: Andy Green

Pitching Coach: Tommy Hottovy

Hitting Coach: Anthony Iapoce

I think there’s no question that Ross is the right fit for the Cubs at this point. Andy Green had good rapport with the young manager, and Hottovy did a terrific job with the pitching staff. While one could make an argument to make a switch from Iapoce, I’m sick of the revolving door at Hitting Coach, and feel he should get to finish his contract in 2021 with the Cubs.

Free Agency Acquisitions

Michael Brantley (LF) – 2 years, $34M:
Entering free agency after a successful two-year stint in Houston, Brantley should see a slight raise on his next team on a similar pact. Age (34 next season) and previous injury history will limit the length of his next deal, but after two injury-ridden seasons in 2016 and 2017, Brantley has played three full seasons, slashing .309/.368/.484 with a wRC+ of 129. Even better, his strikeout percentage is a paltry 10.6 percent in that time frame, providing the Cubs with a necessary contact-hitter from the left side that still brings some pop (22 home runs in 2019, five this year in 47 games).

His defense is still capable (4.7 UZR in 2020), an important aspect of his game considering the DH will reportedly not return to the NL in 2021. Maybin is also a perfect complement, able to start against tough lefties and give Brantley some rest once a week.

One new bat won’t fix what ails the Cubs offense, but Brantley would be a sage investment for a team needing to shore up its contact rate.

Kevin Gausman (SP) – 3 years, $39M, Mutual Option ($18M) in 2024: 
The Cubs need a starter, and the tight budget (along with extensions and Brantley signing) make them non-players in the top of the market. While Trevor Bauer or Marcus Stroman look great on paper, it’s clear the budget won’t allow for such a splash.

Enter Gausman. The former top prospect for the Orioles has had an up-and-down career, but quietly turned in a brilliant 2020 season. A 3.62 ERA (3.09 FIP) with terrific walk (6.5 percent) and strikeout (32.2) rates, Gausman would make for a savvy signing to slot into the middle of the rotation. His fastball velocity (95.1 mph) was up from the previous couple seasons, and at age 30 next year, there’s reason to believe he’d make a solid impact — especially for a team with the Cubs’ pitching infrastructure.

The starting pitching market is somewhat thin, so interest should be heavy for Gausman. A three year guarantee with a mutual option (that includes a hefty raise) should be enough to persuade him to the Northside, cementing the top three arms in the rotation for the Cubs through 2023. The signing also allows Mills to return to his more suitable role as long-reliever/emergency starter.


Kyle Schwarber to the Twins for prospects Landon Leach (RHP) and Cody Laweryson (LHP): 
With Nelson Cruz set to become a free agent and seeking a two year deal (at age 40) the Twins will need a replacement at DH. For a team that notoriously doesn’t break the bank in free agency (outside of the Josh Donaldson signing), taking a flyer on a power-hitter with upside in a contract year would make some sense. Schwarber’s salary will be anywhere from $7-$9 million, an affordable figure for Minnesota while saving the Cubs a few bucks.

The Cubs get two lottery tickets in return, adding pitching depth to a farm system that sorely needs it. This obviously isn’t the ideal return for Schwarber, but after another disappointing season, the clock has run out on the hope he’d be a cog in the middle of the lineup.

Winter Wrap-up

My approach for this offseason attempted to be realistic yet creative. Changes have to be made, but those changes are limited given the financial inflexibility, lack of trade value from members of the core, and a need to be competitive in 2021 while building for a future window of contention. My roster construction provides hope of a division winner while maintaining a flexible mindset. The front office would be in a position to buy or sell if need be at the trade deadline.

I stated in the introduction my doubts that the payroll will approach the Luxury Tax ($210 million.) With the moves I’ve made, the Cubs would be looking at a 2021 payroll of ~$197 million, so I’m admittedly a bit ambitious. Nonetheless, the payroll would be beneath the Luxury Tax by a decent clip, and the Cubs would have a competitive team in 2021 before gaining more financial flexibility after the season.

This team is far from ideal, and places considerable hope in the current core, but the moves (in my estimation) remain realistic while fielding a playoff-caliber roster.

1. Happ (CF)
2. Brantley (LF)
3. Contreras (C)
4. Rizzo (1B)
5. Bryant (3B)
6. Heyward (RF)
7. Baez (SS)
8. SP
9. Hoerner (2B)

Bench Players

C/INF: Caratini, David Bote, Kipnis

OF/DH: Maybin, Hamilton


Starting Rotation: Yu Darvish, Kyle Hendricks, Gausman, Adbert Alzolay, Lester

Bullpen: Craig Kimbrel (CL), Jeffress, Rowan Wick, Kyle Ryan, Jason Adam, Tepera, Mills, Burl Carraway

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

All stats courtesy of Fangraphs.

Featured Photo Credit: Jim Mone, Associated Press

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