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30 in 30

30 in 30: The 2020 Chicago Cubs

“Sitting out (the playoffs), it just sucks,” National Treasure Anthony Rizzo said. “Why didn’t we put it together and win?”

Wrigley by Rob Pongsajapan is licensed under CC BY 2.0

30 in 30: The 2020 Chicago Cubs

Estimated Reading Time: 8 Minutes

We are continuing our 30 in 30 series with a team that said: “Sitting out of the playoffs sucks.”

The past season was not a great one for the once-dominant Chicago Cubs. The Cubs finished with an 84-78 record resulting in a third-place finish in the National League Central. This was the first time in five seasons the team missed the playoffs and should prompt immediate changes.

Before checking in on 2020, we must go back and analyze 2019. 

2019 Season In-Review


Firstly, Pitcher Yu Darvish seemed to resurrect his career. His first half of the season didn’t start out well as he posted a 5.01 ERA and 49 walks in 87 innings. In the second half, however, Darvish seemed to find himself. He finished the second half with a 2.76 ERA with just seven walks over 81.2 innings pitched helping boost his total strikeouts to 229 over the course of the season. Darvish became a key contributor down the stretch even to the point where there was a possibility he would start game one if they made the playoffs.

The Cubs also brilliantly traded for Detroit Tigers’ outfielder Nicholas Castellanos mid-season. Castellanos, in some ways, was the main reason the Cubs stayed in the playoff race. He slashed .321 with 16 homers and 1.002 OPS in only 51 games. Castellanos is a free agent and both teams have mutual interest in him returning.

Finally, aside from a rash of in-season injuries, the main highlight was outfielder Kyle Schwarber, who finally began to show his potential by posting a career-high .871 OPS with 38 homers.

Update: Castellaneous made a decision to sign with division rival Cincinnati Reds as of 1/27/20.


It all started with bad offseason signings.

Two of the team’s offseason signings of IF Daniel Descalso (FA, 2/$5M) and SP Kendall Graveman (FA, 1/$575K) were awful. Descalso, (viewed as a depth signing) finished with a .173 batting average, 25 RBI’s and was barely used all season. This was an awful signing in wake of the Cubs letting go of All-Star Tommy La Stella in the offseason (.295 Batting average, 16 home runs, 44 RBI’s).

I have never heard of Kendall Graveman.

The most significant signing happened in-season when the Cubs surprised everyone with the signing of closer Craig Kimbrel (3 years, 43 million). It didn’t work out- Kimbrel bombed finishing the season only pitching 20.2 innings with a 6.53 ERA while giving up 12 home runs. (Notwithstanding multiple injuries). A Boston Red Sox website went as far as calling his 2019 a “disaster

The seven-time All-Star has given up 15 runs over 20 2/3 innings pitched, good for a career-high 6.53 ERA. Despite only pitching a third of the season, the righty set a new career-high in home runs allowed with nine. Had Kimbrel pitched a full season, he would’ve been on pace to set a new career-worst in walks, strikeouts per nine innings, and strikeout-to-walk ratio.

It’s fair to wonder if he’ll ever be the same pitcher again. At 32 years old and coming off back-to-back seasons trending in the wrong direction, I doubt he will be.

Pitching regression didn’t help

The two most important pitchers, John Lester and Jose Quintana, severely regressed. Aside from a red-hot start to the season, Lester struggled with a 4.46 ERA in 171.1 innings pitched. It appears that father time may have caught up with him at age 36. On the other hand, Quintana had his worst season with the Cubs finishing with a win-loss record of 11-9 and an ERA of 4.68.

Side note: In my opinion, as a Cubs fan, the Cubs’ biggest mistake post the 2016 Championship was the trade of Jose Quintana for top prospect Eloy Jimenez. (31 home runs, 79 RBI’s in his first season. I’m not the only one who shares this sentiment.

It all blew up in September

The 2019 season can’t be remembered without the team’s epic collapse in the final month of the season. On September 17th, the Cubs were only trailing St. Louis by two games for the division and led the Brewers by one game in the wild card. And then September 18 happened. The Cubs epically collapsed which was highlighted by a nine-game losing streak at the worst time of the season. The worst part about this? The St. Louis Cardinals eliminated the Cubs, clinched a playoff birth against them, and even clinched the NL Central against them.

The team didn’t take this well:

Sitting out (the playoffs), it just sucks,” Anthony Rizzo says. “You set out goals in spring of what you want to accomplish, and as an organization we didn’t do that. We held ourselves to a high standard, and it’s up to everyone to figure out why. Why didn’t we put it together and win?”

Star first baseman Anthony Rizzo on the season



On September 29, 2019, the Cubs and long-standing, world series manager Joe Maddon decided to part ways after a long run. Maddon needs to be applauded and labeled the greatest manager in the history of the Cubs. Maddon led the team to 90 wins and clinched a playoff berth in his first four seasons with the team. It was time for the two to part.

Theo Epstein reflected of his relationship with Joe during the two’s almost too cordial exit interview:

“I love him,” Epstein told reporters, describing how the two men met in his hotel room, splitting “a really nice bottle of wine.” “Several,” Maddon interjected with a smile.

“We spent probably 30, 40 minutes together really celebrating an unbelievable five-year run,” Epstein said. “We thought back to when we first got together down at the beach in Pensacola. We never could have imagined this working out as well as it did. I never could have imagined having such a wonderful partner, someone so loyal and supportive, someone from whom I learned so much about baseball and life and someone who I consider a lifelong friend. And our friendship continues. We just talked about it.”

Aside from a brief flirtation with an Astros bench coach, the team hired the man who had been rumored all season to replace Maddon:


The Cubs made the move everyone expected by hiring their former team leader David Ross to a three-year deal. Upon hire, Ross was ready to discuss what went from about the team and immediately expressed the importance of “winning multiple championships.” Theo expressed “absolute trust and confidence: in Ross, who was Theo’s special assistant in the 2018 season.

His ability to finally hold the team accountable, which is needed after Joe Maddon’s loose style lost the team:


Once again, due to issues with the luxury tax, the team elected to stay silent up to this point in free agency. The most significant signing to this point was for outfielder Steven Souza, who missed the 2019 and most of his 2018 season due to multiple injuries. In 2017 he hit 30 home runs and 78 RBI’s for the Rays. Other than Souza, the Cubs continued to sign no-name bullpen arms in the hope they won’t continue to spend 65 million on an unreliable bullpen.

On the other hand, the Cubs were hit hard on player retention, losing key contributors in Bullpen arms Steve Chizek (White Sox) and Brandon Kintzler (Marlins). The Cubs also got punched in the face by the Cincinnati Reds who signed their top hitter (Nicholas Castellanos) and top bullpen arm (Pedro Strop).


The Cubs must be in a dilemma with their former MVP third baseman Kris Bryant. The team and Bryant are dealing with an issue dating back to when he was called up in 2015. That season the Cubs waited to bring Bryant to the big league roster until the first two weeks of the season had elapsed. By doing so, the Cubs were able to push Bryant’s free agency back by one year, giving them seven years of control versus six. Bryant filed a grievance against the Cubs in the case, saying that the team had unfairly manipulated his service time to gain an extra year of control over his contract status.

Ultimately the arbitrator disagreed, leaving Bryant under team control for the next two seasons and makes him that much more enticing as a trade chip.


Projected Line-Up:

  1. Anthony Rizzo- 1B — .286 average, 28 home runs, 101 RBI’s
  2. Kris Bryant- 3B– .283 avg, 28 home run’s, 74 RBI’s
  3. Javier Baez- SS– .319 avg, 30 home runs, 94 RBI’s
  4. Kyle Schwarber- LF– .242 avg, 35 home runs, 79 RBI’s
  5. Jason Heyward—CF– .259 avg, 14 home runs, 56 RBI’s
  6. Wilson Contreras—C– .268 avg, 19 home run’s, 59 RBI’s
  7. Ian Happ- RF– .235 avg, 21 home runs, 64 RBI’s
  8. David Bote—2B– .248 avg, 10 home runs, 38 RBI’s

Projected rotation:

  1. Yu Darvish- 11-9 record, 3.90 ERA
  2. John Lester- 10-10 record, 4.11 ERA
  3. Kyle Hendricks- 12-8 record, 3.66 ERA
  4. Jose Quintana- 11-9 record, 3.96 ERA
  5. Tyler Chatwood- 5-5 record, 4.55 ERA

Projected Bullpen

  1. Long Relief- Duane Underwood Jr./Trevor Megill
  2. Middle Reliever- Brad Wieck
  3. Middle Reliever- Ryan Tepera
  4. Setup Man- Kyle Ryan
  5. Setup Man- Rowan Wick
  6. Closer- Craig Kimbrel


  1. Albert Amora– OF
  2. Steven Souza (FA signing)— OF
  3. Hernan Perez – 2B
  4. Victor Cartini– C
  5. Robel Garcia— 3B
  6. Nico Horner– SS


Tuesday was a rough day for me as a Cubs fan. The Los Angeles Dodgers traded for Mookie Betts which more than likely ending our faint World Series hope.

In response, I believe that the team needs to act now by trading Kris Bryant.

This potential Bryant trade hangs this season in the balance. The Cubs are likely only trading him for a haul and they won’t be as dumb as the Red Sox, But the team must act urgently to begin restocking their awful 29th ranked minor league through a trade like this. This type of trade will open the team’s contention window beyond 2021, when Bryant will likely leave in free agency without the team gaining any compensation back.

The NL Central also looks loaded. The Cardinals are defending champs and are possible suitors for star Nolan Arenado (My worst nightmare). The Brewers will have Christian Yelich at full strength. The Reds are ready to punch the Cubs in the mouth again and might be favorites.

I know this article is really negative. On the positive, we have to consider David Ross as a possible Alex Cora for this team (Cora won the championship with the Red Sox in his first season as manager). Ross’ grit could absolutely set a fire under this team and lead them on a 100-win tear.

It’s possible but I wouldn’t bet my house on it.

I don’t see this going well. I can’t trust Darvish yet, Lester might continue to decline, Tyler Chatwood will be the first starter(!?:/), the Bryant issue will hang over the team somehow, and some players will likely push back to Ross. It looks too much to overcome.

Prediction: 80-82, Fourth in NL Central.

I’m taking the UNDER of 85 wins.

Tim is a grateful believer, husband to Kristin, Father to Isabelle living in Los Angeles as both an actor and Claims adjuster. He was born and grew up eight blocks from Wrigley Field and is a die hard Chicago fan (Especially Bears). He is incredibly grateful to The Turf for giving him a chance to pursue a passion of his.

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