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SB Nation Offseason Simulation: The fake 2020 Cubs

All the SB Nation sites got together for some simulated wheeling and dealing.

Photo by Nuccio DiNuzzo/Getty Images

Whereas the 2014-18 seasons were all some form of success for the Cubs — from building a winner to winning a championship to sustaining 90+ wins and continually playing October baseball — 2019 was a flop. Winning 84 games as a luxury taxpaying team simply doesn’t cut it. For that failure, Joe Maddon was allowed to sail west to California and the Theo Epstein / Jed Hoyer regime received a condemnation from the Chicago media and the Cubs’ fan base.

Thankfully, baseball provides a great reason for optimism: 2020 is coming! Sure, there may be some anxious free agent negotiations and even some snowstorms along the way, but 2020 will arrive soon enough.

This week, I had the pleasure of participating in the SB Nation Offseason Simulation project run by the good folks at Royals Review. Each team was represented by a general manager and teams negotiated free agent contracts with one super-agent who acted like a real agent, sometimes trying to upsell interested teams and occasionally eschewing the most cash for an opt-out, no-trade clause, or winning ball club. What follows is a summary of my approach to the Simulation, what actually happened, and what the Fake 2020 Cubs look like.

I discussed this in greater detail in last year’s post, but the building phase was easier than the sustaining phase. Now, the task is even tougher: rebuilding on the fly...or tearing things down quickly...or something else? The 2020 Cubs could go in a whole bunch of different directions.

Thankfully, this year’s simulation featured an ownership directive for each team instead of a static budget. The pretend notes from Tom Ricketts felt dead-on to me: “Get us under the luxury tax threshold and be creative to field a sustained winner. Move core players if you need to. We may need to shake things up, even if it means taking a short-term hit this year, but I want us back on top in the near future.”

With those marching orders, I set out my list of goals:

  • Win the 2020 World Series. The Cubs should be able to make the playoffs, and just about any playoff team can win the World Series.
  • Accumulate Talent and Find Value. This is what the best teams do.
  • Test the Waters for Unloading Unwanted Salary. Anybody else going to miss Tyler Chatwood, Daniel Descalso, or Jason Heyward on the books? Didn’t think so.
  • Acquire Major League or Major League-Ready Arms. Last year, the Cubs’ luck with bullpen arms and veteran veteran starting pitcher health finally ran out. The club is heading for a transition in the rotation with both Jon Lester and Jose Quintana quite possibly in their final year with the team. Adbert Alzolay offers some internal excitement (albeit with health issues), guys like Justin Steele and Alec Mills can fill in if needed, and Brailyn Marquez is rumbling down the tracks, but the Cubs need more quality arms across the board.
  • Find a Real Centerfielder. I wasn’t an Albert Almora Jr. fan before the 2012 draft, I didn’t like him as a prospect, and I sure don’t want to count on him in 2020.
  • Get Better on Defense. The 2019 Cubs really struggled in the field. That irked me.
  • Find a Defense-First Veteran Catcher. This is likely my most controversial position. Willson Contreras’ glovework simply isn’t getting the job done and his offense can’t fully make up for his defensive shortcomings and injury issues. The Cubs need a better safety net here...or perhaps even a new starting-caliber guy to pair with Victor Caratini.

With those goals in place, I embarked on the journey. Come along for the ride!

I began the simulation by floating a league-wide memo detailing my position: Javier Baez, Anthony Rizzo, and Kyle Hendricks won’t be moved while Jon Lester and Yu Darvish cannot be dealt due to their no-trade clauses. Everyone else in the system is on the table, including Kris Bryant, Willson Contreras, Kyle Schwarber, Jose Quintana, Tyler Chatwood, Kendall Graveman, Albert Almora, Daniel Descalso, Ian Happ, and more.

Contreras gained the most traction, which wasn’t exactly surprising given the dearth of quality bats at the position. Happ came in right behind him: it seems as though his massively decreased strikeout rate stood out to more teams than just the Cubs. Bryant and Quintana also got some nibbles initially.

When it came time to decide on contract options and non-tenders, I had a pretty easy go of it.

Option Decisions

  • Exercised: 1B Anthony Rizzo ($14.5M), SP Jose Quintana ($10.5M)
  • Declined: RP Brandon Morrow ($3M buyout on $12M option), RP Derek Holland ($0.5M buyout — paid by San Francisco — on $7M option), RP David Phelps (no buyout on $5M option), RP Tony Barnette (no buyout on $3M option)


  • SS Addison Russell ($5.1M arbitration estimate)

Nobody wanted anything to do with Russell at any price as he went unsigned.

You may have noticed one option decision that went unmentioned above, which brings me to my first external transaction of the Simulation:

Transaction #1: Cubs exercise $3M club option on SP Kendall Graveman and trade Graveman to Toronto for C Riley Adams

Adams isn’t some huge coup. He’s a 2017 third-round pick for Toronto that will need to have his pop carry him to the Majors. He had a very nice offensive season in the mid-minors last year, but his glovework will never be plus. No matter: this was about trading nothing for something.

As the trade discussions continued with a flurry, I moved into full-on catcher acquisition mode. I knew I wouldn’t be entering the fray for Yasmani Grandal, who ended up with a hilarious six-year, $150M deal from the White Sox, so my focus was on four free agents — Jason Castro, Martin Maldonado, Alex Avila, and Russell Martin — and seven trade targets: Sean Murphy, Roberto Perez, Christian Vazquez, Austin Hedges, Jake Rogers, Jorge Alfaro, and Tyler Flowers. Some of those would be expensive while others would be cheap, but all of them were targeted due to their plus framing skills combined with palatable contracts and at least enough offensive success to play regularly. I thought that I had a good shot at Perez and I’d love to see his defense on the Cubs, but it didn’t work out.

Thankfully, given that number of options, I found what I considered to be an idyllic outcome:

Transaction #2: Cubs sign C Jason Castro to a one-year, $2M contract with a $4M club option ($0.5M buyout)

Awesome. I am a big fan of Castro. He is a plus framer with slightly below-average offense most years coming off of a year with serious pop (.203 isolated power). Injuries have been an issue, but I’m not expecting him to play 100 games with Caratini around. This was a great fit. And it allowed me to make an even bigger splash.

Transaction #3: Cubs trade C Willson Contreras, RP Tyler Chatwood, and 2B Daniel Descalso to Detroit for SP Matt Manning, SP Alex Faedo, and SP Joey Wentz

This was the blockbuster. I wanted to test the waters with Contreras for the reasons mentioned above, and Detroit proved to be a club in search of a splash behind the dish. They also come complete with tons of arms with which to repopulate the Cubs’ system with some serious upside.

After some back and forth, I gave Detroit two options: an option where they included an additional prospect that I liked and an option where they absorbed some unsightly salary. They chose option two. While I genuinely like Chatwood and would be happy to keep him around, he’s still underwater by at least $10M given his $13M salary, so this was a big help in clearing room to get under the tax line of $208M, even though I would’ve been happy to keep Chatwood and get SP Tarik Skubal from the Tigers instead.

With my most significant move already completed, I thought the team had two divergent options for the 2020 season: a one-year dip with a mini-rebuild or true contention. As a way to answer the question, I turned my focus to seeing what the market held for Bryant. It’s no secret that the Cubs will get a feel for what’s out there for KB, but I’m governed largely by the fact that Bryant is a genuine superstar with two years (we think) of mandatory team control, plus the draft pick compensation that would come if he departed as a free agent. That’s a tasty package. I got into significant discussions with the Phillies and the Rays — detailed below — but something else happened rather quickly that changed my thinking on Bryant.

The Pirates came calling about some of our young, high-upside pitching. They initially wanted Marquez, who I adore, and we didn’t get much traction. But when they started espousing affection for SP Riley Thompson and SP Yovanny Cruz, it was clear that we had a chance to make a real move. I just didn’t appreciate how significant this would be:

Transaction #4: Cubs trade SP Riley Thompson, SP Yovanny Cruz, and SP Kohl Franklin to Pittsburgh for CF Starling Marte, RP Keone Kela, and $6M


While I’m infatuated with Marquez, Thompson isn’t close to the same tier. He’s a nice prospect, but he’s the kind of guy that the Cubs can always find; Thompson received an $200K bonus as an 11th-round pick in 2018. Cruz and Franklin both come with much more significant ceilings, but the opportunity to add a plus centerfielder on a below-market deal and a closer-type reliever with two years of arbitration control made this seriously compelling. The fact that I made this deal without surrendering Nico Hoerner, Miguel Amaya, Marquez, Alzolay, Brennen Davis, Cole Roederer, Ryan Jensen, etc. made it a no-brainer. The metrics didn’t like Marte’s work in center last year, but I trust his athleticism and the ability to change the metrics’ mind by moving from spacious PNC to Wrigley.

This deal changed my approach in the Simulation from “find value wherever it is” to “we’re contending in 2020.” Shortly after finalizing the trade, I got my top free agent reliever target to sign as well:

Transaction #5: Cubs sign RP Chris Martin to a two-year, $15M contract

I’m way in on Martin. He has been stellar since returning to the States with Texas in 2018, utilizing a four-pitch mix to rack up strikeouts despite walking less than one batter per nine.

I was done with my notable deals at this point, so I turned my focus to the most significant deal possible: a Bryant trade. I ended up with two reasonably significant offers.

Philadelphia Offer: 3B Alec Bohm, SP Adonis Medina, OF Mickey Moniak, and SP Enyel De Los Santos

It’s not a bad offer. Bohm was the third overall pick in 2018 and is a consensus top-50 prospect with half a year at Double-A under his belt. He probably doesn’t have the chops for third, though, and that hurts his value a lot in my eyes. Medina is a former top-100 prospect who plateaued at Double-A last year. Moniak was the number one overall pick in 2016 and has the look of an all-time whiff. De Los Santos is MLB ready, though he’s probably a fastball-changeup reliever.

However, I insisted on Philadelphia including SP Spencer Howard and I never got any clarity as to whether they’d do so. A Bohm-Howard-Medina package is pretty attractive, even though I’m low on Bohm.

Tampa Bay Offer: SS Brendan Rodgers (from Colorado), SP Shane Baz, and one of 2B Vidal Brujan or SP Shane McClanahan

This was the far better, yet far riskier, offer. Rodgers is a superstar in the making in the vein of Bryant, especially if he slides to an easier defensive spot at 2B or 3B. He has premium power and six years of cheap control. Unfortunately, he also missed most of 2019 and finally underwent shoulder surgery late in the summer, though he is supposed to be ready when spring training begins. Baz is a premium arm with a nice arsenal, but he’s heading to High-A in 2020. Brujan is a no-power leadoff threat with elite speed that should reach the Majors by late 2020. McClanahan is a lefty who has been extremely productive and risen quickly as a 2018 compensation round pick, but he needs some more seasoning and comes with Tommy John in his past.

We also discussed massive lefty Matthew Liberatore, the 16th pick in 2018 and a top-50 prospect. I like Liberatore more than any of the other secondary pieces, but he was a sticking point for Tampa.

Had I been able to get Rodgers, Baz, and Liberatore, I would’ve pulled the trigger, despite the lack of help they would’ve given the 2020 club. But that offer couldn’t get there and my potential replacement — Josh Donaldson — signed for $90M over four years with Atlanta, so Rodgers got shipped to the Cardinals instead. Gulp.

Obviously a potential Bryant deal would have seismic ramifications for the Cubs in 2020 and beyond. But not the simulated Cubs. We’re keeping KB.

Now, we enter the lightning round:

Transaction #6: Cubs trade 2B Vimael Machin to Oakland for SP Hogan Harris

Oakland was obsessed with Machin despite his lack of pedigree and advanced age. I gladly took a flyer on their injury-riddled 2018 third rounder who posted a WHIP under one with just over a strikeout per inning at High-A last year.

Transaction #7: Cubs sign RP Pedro Strop to a one-year, $1.5M contract

Deserved Run Average over at Baseball Prospectus suggests that Strop was actually good in 2019. My eyes told me a different story. But given his cold market, this was a safe risk to take in the hopes that BP was right.

Transaction #8: Cubs sign RP Francisco Liriano, RP Tommy Hunter, and RP Nate Jones to minor league contracts

Spring Training, here we come! Catching lightning in a bottle with one of these guys sure would be great.

At this point, the offseason was nearly complete. Nevertheless, I got some nibbles on Alec Mills and initiated another conversation about a pitcher in whom I have a good bit of interest. Turns out, we happenstanced our way into a match:

Transaction #9: Cubs trade SP Alec Mills to New York Yankees for SP Jordan Montgomery

I loooooove this deal. Montgomery missed almost all of 2018 and 2019 with ill-timed mid-2018 Tommy John surgery. But he did return late last year, showing the same stuff that made him a 2.5-WAR starter as a rookie in 2017. He has a solid arsenal and consistently good — if not great — results. While Mills should have a job on the 2020 Cubs, I like Montgomery more as a pitcher and, importantly, Montgomery has an option remaining whereas Mills does not. I wanted a couple of guys who could ride the Chicago-to-Des Moines shuttle, and Montgomery was a dream come true on that front.

I’ll detail the end result below in a moment. For now, here are some other targets about whom I had significant discussions:

  • RP Ken Giles: Toronto simply got a better deal
  • RP Mychal Givens: Baltimore wanted something for him — not unreasonable — and I didn’t want to give up anything. Tough to find a match there.
  • RP Jose Alvarado: He’s a huge lefty who throws hard. Tampa liked him as much as I did, which makes dealing tough.
  • SP Julio Urias: I though we had some traction here, but then the Dodgers’ GM went AWOL
  • RP Joe Kelly: See above.
  • SP Marco Gonzales: He’s a tough nut to crack as his production improved as his velocity cratered.
  • RP Ian Kennedy: He’d be a great target for the Cubs with Kansas City paying down a chunk of his salary.

On the other side, there was a ton of interest in prospect SP Cory Abbott and Ian Happ with a bit of interest in Quintana and no interest at all in Schwarber.

With those moves completed and the offseason wrapped up, here are your fake 2020 Cubs using the Steamer WAR projections and 2019’s non-COLA’d minimum salary:

2020 fake Cubs pitchers

Pos. Name 2020 Salary 2020 Tax WAR
Pos. Name 2020 Salary 2020 Tax WAR
SP Lester, Jon $25,000,000 $25,833,333 2.1
SP Darvish, Yu $22,000,000 $21,000,000 3.8
SP Hendricks, Kyle $12,000,000 $13,875,000 2.7
SP Quintana, Jose $10,500,000 $10,500,000 2.5
SP Montgomery, Jordan $1,200,000 $1,200,000 1.5
RP Kimbrel, Craig $16,000,000 $14,333,333 1.2
RP Martin, Chris $7,500,000 $7,500,000 0.8
RP Kela, Keone $3,400,000 $3,400,000 1.2
RP Strop, Pedro $1,500,000 $1,500,000 0.2
RP Ryan, Kyle $1,100,000 $1,100,000 0.4
RP Wick, Rowan $555,000 $555,000 0.5
RP Underwood, Duane $555,000 $555,000 0.1
RP Wieck, Brad $555,000 $555,000 0.5

2020 fake Cubs position players

Pos. Name 2020 Salary 2020 Tax WAR
Pos. Name 2020 Salary 2020 Tax WAR
C Castro, Jason $2,000,000 $2,500,000 1.7
1B Rizzo, Anthony $14,500,000 $14,500,000 4.1
2B Hoerner, Nico $555,000 $555,000 1.4
3B Bryant, Kris $18,500,000 $18,500,000 4.7
SS Baez, Javier $9,300,000 $9,300,000 3.3
LF Schwarber, Kyle $8,000,000 $8,000,000 3.2
CF Marte, Starling $11,500,000 $11,500,000 2.7
RF Heyward, Jason $21,000,000 $23,000,000 2.0
C Caratini, Victor $555,000 $555,000 1.1
IF Bote, David $950,000 $3,000,000 0.5
IF Kemp, Tony $555,000 $555,000 0.2
OF Almora, Albert $1,800,000 $1,800,000 0.2
OF Happ, Ian $555,000 $555,000 1.2

Not bad. Not bad at all.

Almora is listed above on the 26-man roster, but the plan would be for him to spend the year getting daily plate appearances in Iowa instead. Additionally, I adjusted Happ downward and Hoerner and Montgomery upward based on my own playing time estimate.

In the end, the total player payroll for that group is $188,635,000 with a luxury tax payroll — including a $13M estimate for player benefits — of $203,226,666, about $4.7M under the tax threshold.

Steamer estimates that the position players would produce 26.3 WAR and that the pitchers would produce 17.5 for a total of 43.8. Last year’s real-life Cubs produced 41.9, so you may look at the above and say “meh.”

But, unsurprisingly, I disagree for the following reasons:

  1. Ownership would be extremely pleased by this cut to payroll paired with even a slight increase in expected production and as a fake GM, ownership’s happiness is paramount.
  2. More importantly to this writer as a fan, there is a real influx of hope on the farm. Manning, in particular, offers the type of realistic ceiling that the Cubs don’t currently have on their farm, and he’s ticketed for Triple-A to begin 2020 with a strong shot to join the rotation during the year.
  3. Hendricks has consistently outperformed projection systems, and there’s a decent chance that both Quintana and Lester do as well.
  4. The bullpen. Jeez. The bullpen surely isn’t perfect as constructed, but having Kimbrel AND Martin AND Kela AND Wick AND Ryan provides a bullpen that should be able to better protect leads than in years past. Anything from Wieck, Strop, Underwood, James Norwood, Dillon Maples, Danny Hultzen, etc. would be gravy.

So there you have it. We increased the projected production of the team and significantly improved the state of the farm system, all while cutting payroll in the process. But what do you think? Would you be happy with this type of offseason?