Woof, Theo and Jud, Woof

In 2019, the Cubs finished 3rd in the Central and missed the playoffs. They underperformed their Pythagorean record by 6 wins (Pythagoras said 90, they won 84). The Brewers won 89, outperforming their Pythagorean record by 8 wins.

In 2020, the pandemic shortened season, the Chicago Cubs won the NL Central with a .567 win%, a 92 win pace.

The 2019 Cardinals won the NL Central. In 2020, they were 3 games back of the Cubs, and played at an 84 win level.

While the Cards kept winning in 2021 and 2022, the Cubs became uncompetitive.

Let's see how the Cubs mismanaged their roster.

Heading into 2021, the Cubs were pretty good. They had a weak but improving farm. They had an aging roster, but a reasonable remaining core. There were five years past their 2016 title, and they had failed to refresh their core.

2020 Cubs - $199M Paryoll



2020 age

Key stat

fwar * 2.7


Wilson Contreras


110 wRC+



Anthony Rizzo


103 wRC+



David Bote


92 wRC+



Javier Baez


57 wRC+



Kris Bryant


77 wRC+



Kyle Schwarber


91 wRC+



Ian Happ


132 wRC+



Jason Heyward


131 wRC+



Yu Darvish


31.3% K



Kyle Hendricks


3.55 FIP



Jon Lester


5.14 FIP



Alec Mills


5.44 FIP



Jose Quintana


2 IP



Rowan Wick


2.67 FIP



Ryan Tepera


35% K



Nico Hoerner


5.1 DEF


After 2020, the Cubs non-tendered Kyle Schwarber. Schwarber hit to a 145 wRC+ in 2021 and 128 wRC+ in 2022. The Cubs would have controlled his rights through 2022. Prior to 2022, he signed a 4yr $80M deal with the Phillies.

They also declined Jon Lester's option. He signed with Philly and ended his career in St. Louis in 2021, but he wasn't good.

The Cubs let Quintana walk after 2020. He signed a 1yr, $8M deal with LAA. The Angels waived him and the Giants claimed him. Quintana only threw 63 innings in 2021. For 2022, the Pirates signed him for 1 year, $2M. Quintana put up 4 fWAR in 2022.

The Cubs also traded Yu Darvish, Victor Caratini, and cash to the Padres for Zach Davies, Reginald Preciado, Owen Caissie, Ismael Mena, and Yeison Santana

By June 1, 2021, the Cubs were in first place in the NL Central at 31-23. The Cardinals were 31-24. The Brewers were 29-26.

The Cubs lineup on 6/1/21 was Contreras, Bryant, Rizzo, Baez, Happ, Wisdom, Joc Pederson, and Sergio Alcantara with Kyle Hendricks pitching and Craig Kimbrel getting a save.

By July 1, 2021, the Cubs were in 2nd place at 42-39. The Brewers were 49-33. The Cards were in 4th at 40-42.

By the trade deadline, the Cubs had started their fire sale. Let's see how they did.

Cubs Traded



Kris Bryant

Alexander Canario, OF, and

Caleb Kilian, RHP

Fine, no stars

Javier Baez, Trevor Williams

Pete Crow Armstrong

Good return

Criag Kimbrel

Nick Madrigal and

Codie Heuer

Fair, Heuer TJS, Madrigal no power

Jake Marisnick

Anderson Espinoza

Nothing for nothing

Anthony Rizzo

Alexander Vicaino RHP

Kevin Alcantara, OF

Good, Alcantara has potential

Ryan Tepera

Bailey Horn

Not much

Andrew Chafin

Greg Deichmann OF

Daniel Palencia RHP

Nothing for nothing

Joc Pederson

Bryce Ball 1B

Not much

Yu Darivsh, Victor Caratini

Zach Davies,

Reginald Preciado,

Owen Caissie,

Ismael Mena, and

Yeison Santana

Potential, but far away. Darvish has been great, the Cubs are still paying him, and Davies was terrible

With all their deals, the Cubs cut their payroll to $150M in 2021.

For 2022, the Cubs held their payroll stable at $146M, down just $4M from 2021. They signed Marcus Stroman (opt out after 2023), Seiya Suzuki (8yrs, $184M), claimed Wade Miley, signed Yan Gomes 2/$13M and Drew Smyly 1 yr/5.25M.

At the 2022 deadline, the Cubs only made minor moves, despite Contreras being a FA at the end of the season.

So, the Cubs saved a fair amount of money, but they lost a lot of games. They also got a lot of young players, and a few might be good. The thing is, the trades really highlighted how terrible the Cubs minor leagues were. Without the prospects acquired, the Cubs would have a frighteningly bad system.

The Cubs could have done things differently.

Dropping Schwarber was a big mistake. He has been worth 2.5 fWAR/year since then.

The Darvish trade was bad. He's averaged 3.5 fWAR/year in SD and the Cubs are still paying him. At $21M/year, his contract was a good deal for the club. The prospect return is still years away.

Rizzo has continued to be solid, and he signed a reasonable deal with the Yankees after they acquired him.

The Cubs should have gotten more for Kris Bryant. They ran out of leverage, and they achieved nothing with the deal. He only played 42 games in his first year in COL.

For 2023, the Cubs look unlikely to compete. Their rotation is Stroman, Steele, Hendricks, and it looks very average. The team's core is Happ (27), Hoerner (25), and Suzuki (27). Franmil Reyes is fine. Christopher Morel might be ok. Nick Madrigal could bounce back. For $161M so far, the Cubs have 8.2 fWAR since signing Jason Heyward. That's almost $20M/fWAR.

For having brilliant, expenses leadership in Theo and Hoyer, the Cubs didn't do much well after assembling the 2015-2017 club. They failed to develop starting pitching or subsequent stars. Bryant fell to them because Houston made a dumb pick at 1. Their other stars were either lucky or high picks. The Cubs overpaid for Jose Quintana in prospects and Yu Darvish in salary.

Now the Cubs have an ok farm system, but the prospects have high risk because of contact concerns. The Cubs shaved payroll, but they have no depth. They have some good players, but none that are great.

After building the club for their "dynasty," it seems like the front office and ownership just coasted, pocketing a fortune along the way of course.