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How Theo Epstein Has Already Set the Cubs Up for Future Success

Although Cubs fans have questioned Theo Epstein's decision making in recent years, he's already made moves that have set the organization up for future success.
Theo Epstein Cubs

Photo: Charles Rex Arbogast/Associated Press

It’s no secret the Theo Epstein regime is at a crossroads this offseason. The “competitive window” is close to being slammed shut, and because of this, the 2020 offseason is loaded with questions. Do the Cubs consider trading Yu Darvish or Kyle Hendricks and rebuild? Do they go all in for one last ride? Which of the core should Theo extend?

With all this uncertainty surrounding the organization’s future, fans have started to believe Theo Epstein has put the Cubs in an unfortunate state before his inevitable departure after 2021. I’m here to tell you that is false. Theo Epstein has already made many moves that have set the Chicago Cubs up for future success.

Yu Darvish and Kyle Hendricks’ Cheap Contracts

Constructing a contending team begins and ends with the starting rotation. Teams not only need depth, but they also need ‘Ace’ caliber arms that take the ball every fifth day. It's a requirement if you want a chance to win your division. With this fact in mind, let me ask you this: what organization in MLB wouldn’t sign up for Yu Darvish and Kyle Hendricks headlining their rotation for the next three years? The answer is zero, and that’s exactly what Theo Epstein has given the Chicago Cubs.

Yu Darvish Kyle Hendricks Cubs

Photo: David Zalubowski/AP/Shutterstock

It’s not just that both Darvish and Hendricks have put up sensational numbers in recent seasons. That’s only part of the equation. The other part is this: their contracts are absolute steals. Yu Darvish finished second in the 2020 Cy Young race (personally, I think he should have won it) and has dominated since July of 2019. Guess what his average annual salary is for the next three seasons? $19.7 million. To put that into perspective, Gerrit Cole, Jacob DeGrom, and Stephen Strasburg make $32.5 to $36 million annually over the life of their remaining contracts. Yu Darvish has been just as good or better than all of those 'Aces' the last 1.5 seasons.

Now, let’s get into Kyle Hendricks, the man who touts a career 3.12 regular-season and postseason ERA. No, I’m not kidding. That’s how dominant he’s been during his six-year career. He’s the most underrated MLB player and it’s not close. Because he doesn’t throw hard, looks like a college professor, and isn’t a physical specimen, baseball believed his early success would not be sustainable. The Cubs capitalized on this inept thinking and were able to sign Kyle Hendricks at $14.5 million annually through 2024. Epstein deserves praise for valuing results and production over baseball’s flawed biases.

Mills and Alzolay Under Club Control Through 2025

Remember when Cubs brass was skeptical that Alec Mills and Adbert Alzolay would develop into starting pitchers? Well, the 2020 season flipped that notion entirely. Both are penciled in as starters next season and are under cheap club control (i.e. arbitration) through 2025. Possessing two effective starters that are under arbitration for five more years is invaluable. Theo Epstein deserves credit for fleecing the Royals with the Alec Mills acquisition. And for once, the Cubs look to have successfully developed a homegrown arm in Adbert Alzolay.

Not only did Alzolay put up a very impressive 2.95 ERA in 2020, but he also flashed a new-look slider his last couple of appearances that he developed at the Cubs' taxi squad site in South Bend. See for yourself how filthy it is:

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That’s what a putaway pitch from an MLB starter looks like, and the results back it up. Alzolay struck out eight batters and gave up only one run against a loaded White Sox lineup in his last start. He still has some command issues to improve, but Alzolay has the stuff to be a mid-rotation starter. He just needs to develop the stamina so he can go six to seven innings deep every five days.

Enough with the Alec Mills Disrespect

Alec Mills also put up very effective 2020 numbers. While his 4.48 ERA in 62.1 IP isn’t too impressive on the surface, if you exclude his three blowup starts, he put up a 2.94 ERA in 52 IP. That’s pretty damn impressive. Especially for a guy who an entire section of the media still views as a “fringe starter.” Honestly, it’s laughable that people still have this school of thought. It embodies everything wrong with how baseball overlooks certain perceived "flaws."

Alec Mills is only 28, just tossed a no-hitter against a playoff team, and has a career 3.87 ERA in 116.1 IP as a Cub. If a player who threw 98 MPH had accomplished all that in his young career, MLB would tout him as a future ‘Ace.’ But baseball writes Mills off under a cloud of doubt because he, like Kyle Hendricks, doesn’t touch 90 and isn’t an imposing figure. Give Theo credit for not falling into this ridiculous thought trap.

Theo Epstein's Goal of Post-2021 Financial Flexibility for the Cubs

I understand that, due to Theo Epstein’s inability to extend any of the core, the organization’s future position players are much murkier than the starting rotation. However, the flip side to that uncertainty is a positive. The Cubs have very few “big money” contracts on the books past 2021. The only two are Yu Darvish, which is a bargain given his production, and Jason Heyward, who is coming off his best season as a Cub (JHey is signed through 2023).

Why this fact never sees the light of day is puzzling. Financial flexibility is a requirement if an organization wants a smooth transition from one competitive window to another. If the Cubs had significant long-term money invested, fans would be correct when stating Theo Epstein is leaving this organization in turmoil. But that is not the case.

A Very Formidable Cubs Farm System

For some reason, the idea that the Cubs have a low-end farm system still exists. This is false. The Cubs currently have three top 100 prospects (Brailyn Marquez, Brennen Davis, Miguel Amaya) in addition to Nico Hoerner, who was a top 50 prospect just one year ago. Not only that, nine of the Cubs’ top ten prospects are expected to debut in 2022 or earlier. Do you think it’s a coincidence that the next wave of young talent will be reaching the big leagues right when this current core is hitting free agency? No, it’s not.

This Was Theo Epstein’s Plan All Along

For hypothetical sake, let’s say the Cubs extend Willson Contreras, Anthony Rizzo, and Javier Baez while trading Kris Bryant and Kyle Schwarber (the linked article explains why I think this is the best option). This would mean the Cubs have the following:

  1. Three proven All-Stars signed long-term
  2. Two 'Aces' locked up under team-friendly deals
  3. Two legitimate starting pitchers under arbitration through 2025
  4. A flurry of prospects one to two years away from reaching The Show
  5. A vast amount of money to spend after 2021

What’s that sound like? An organization with a bright future. It’s almost like Theo Epstein, a Hall of Fame executive, had a plan this entire time.