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SB Nation Offseason Simulation: The fake 2019 Cubs

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

Can this player be traded? Find out below!
Photo by Justin Berl/Getty Images

With a full month to look back on it, many Cubs fans can appreciate that the 2018 season was, on the whole and in a vacuum, quite the success. The Cubs got a breakout season from Javier Baez, survived the dreadful debuts of free agent signees Yu Darvish and Tyler Chatwood, enjoyed continued improvement from Jason Heyward’s bat, found a potential key rotation cog for the future in a rejuvenated Cole Hamels, and still finished tied with the most wins in the National League after 162 games. Of course, over about 36 hours in early October, the 2018 Cubs crumbled and meekly bowed out of the postseason. It was tough to stomach.

Thankfully, baseball provides a great reason for optimism: 2019 is coming! Sure, there may be some anxious free agent negotiations and even some snowstorms along the way, but 2019 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 2019 Cubs look like.


Approaching previous offseasons has been rather easy for me. Before the 2014 season, a crummy club still outside of its window of contention needed to continue to accumulate talent and flippable veterans. Before the 2015 season, it was clear that the Cubs were ready to take a leap. Before the 2016 season, it was clear that they were going to take another one, particularly with regard to spending. Before the 2017 season, very little needed to be done to tinker with a stellar squad. And before the the 2018 season, the Cubs needed an infusion of pitching talent, a search that would dominate the offseason. My Simulation strategies largely tracked those of the Theo Epstein/Jed Hoyer regime, even if the names weren’t always the same.

But this year? Good gravy, this year is tricky. The Cubs continue to have needs — a healthy closer and a resolution of Addison Russell’s status with the team stand out — but it seems that, more than anything else, a return to form from the likes of Kris Bryant, Jose Quintana, and Willson Contreras dominates the list. And what is the budget? Are the Cubs going to try to stay just below the luxury tax threshold of $206 million as a matter of course? Or is the club ready and willing to zoom into regular taxpayer territory if it means signing a young, generational talent in Bryce Harper or Manny Machado? Are the recent reports about fiscal constraints a dire warning that the purse strings will be tightened, a preemptive measure to avoid allegations of tampering if Harper does join Bryant with the Cubs, general front office misdirection, or something else entirely? Your guess is as good as mine.

One final note before I get to the goals: the Rangers GM was kind enough to do the Hamels-Smyly option-trade transaction that occurred in real life, so I approached the Simulation with that in hand — it is not a transaction I would have completed were I in Epstein’s shoes. But I’m not.

So, with all of that said, here were my primary goals in approaching the Simulation:

  • Win the 2019 World Series. This isn’t always my top goal — I oftentimes prefer talent accumulation in whatever form — but it was absolutely the driving force.
  • Accumulate Talent and Find Value. This is what the best teams do.
  • Test the Waters for Unloading Unwanted Salary. This is a new goal that I haven’t encountered before. Some of this is obvious: I hoped to find a taker for some/all of Chatwood’s remaining $25.5 million over 2019-20, Brandon Kintzler’s $5 million, and possibly Brian Duensing’s $3.5 million. Some less so: Jason Heyward just entered a two-year stretch of reduced no-trade protection (he can block deals to 12 teams), so I wanted to feel out the market for his $106 million remaining over the next five years. Similarly, Ben Zobrist has just one year and $12 million on his deal, but his no-trade clause just dropped to an eight-team no-trade list. If money is so tight, Zobrist may need to be considered, though surely the Cubs would seek to do right by him.
  • Acquire Major League or Major League-Ready Arms. The Cubs need some new bullpen arms, especially after Joe Maddon threw Steve Cishek an exorbitant 81 times in 164 games and given Brandon Morrow’s injury history. Similarly, the Cubs veteran starting pitchers have enjoyed a remarkable run of health. It’s going to expire at some point, and with only a rehabbed Adbert Alzolay and perhaps Justin Steele around as viable candidates to make a handful of important starts in 2019 (depending on your affection for Duane Underwood or Alec Mills), the Cubs could use another ready-to-go starter or two.
  • Find a Fresh Start for Addison Russell and Replace His Glove. In real life, I suspect that the Cubs will keep Russell or flip him in the next month. If the team planned to release him, I suspect that they already would have done so. Since he’s still on the team, I figured I’d flip him in the Simulation, not expecting much of a market.
  • Find a Defense-First Veteran Catcher. They’re everywhere.
  • Sign Bryce Harper. The Simulation always inflates costs, so I figured that Harper would end up somewhere around $450 million over 12 years, an average annual value of $37.5 million. That’s a lot, but the Cubs are about to print even more money via their broadcast rights. They’re in the select group of teams that can afford such an extreme expenditure, should they choose to do so.

When the Simulation began, I was regularly asked about the same group of players: Kyle Schwarber, Willson Contreras, Ian Happ, Albert Almora Jr., and Adbert Alzolay. I received some solid interest in Victor Caratini and rising righty prospect Michael Rucker. I got one question about Jose Quintana, one about Carl Edwards Jr., and none about the rest of my bullpen.

Interest was certainly heaviest in Schwarber and Happ with Alzolay the third-most requested player. Probably the most enticing offer for Schwarber came from Atlanta who offered up lefty Kolby Allard and righty Kyle Wright. Wright was one of my highest targets, but Happ wasn’t enough to get him. I’ve long been an Allard fan, but while his results have been sparkling, his mechanics and arsenal have all backed up since his prep days. Beyond this, I’m irrationally attached to Schwarber just like most Cubs fans are. It’d take $1.50 on the $1 to move him right now, especially after his bat looked even better a year removed from his knee injury and his outfield defense showed similar strides. He just turned 25. He’s a necessary bat in the middle of the lineup for a World Series contender. Still, Wright was tempting, especially knowing the the Cubs will have to spend to keep members of their position player core in the coming years, necessitating the need for a cheap starter or two.

Easily the most exciting developments in the first day were possibilities with both the Twins and the Giants to talk about Tyler Chatwood. I had raised Chatwood to the Royals as a possibility for their rebuilding club, but they weren’t interested. But the Twins and Giants both saw a pitcher in his 20s with lots of upside and a low cost. The Twins conversation was initiated because of Minnesota’s interest in bringing back Brandon Kintzler. In real life, this is probably the Cubs’s best option as Kintzler recently thrived as the Minnesota closer. At one point, the discussion centered around a deal where the Twins would take Chatwood and Kintzler and send back outfielder Max Kepler. Now, Kepler likely doesn’t stick with the Cubs, but he’s a solid, athletic outfielder. I can do something with him. Kepler ended up getting pulled out for other talks, but the alternative Twins package of prospects outfielder Akil Badoo and righty Jhoan Duran was a dream come true. Unfortunately, it didn’t come to pass and Minnesota wisely used its cash elsewhere.

The Giants offer was similarly ideal. At one point, the framework involved the Cubs sending Chatwood and three prospects (righty Duane Underwood, righty Erling Moreno, and outfielder Nelson Velasquez) to the Giants for righty Jeff Samardzija, lefty Will Smith, and $39 million. Yes, you read that right: the Cubs would’ve unloaded all of Chatwood’s deal, gotten a good closer in Smith, and acquired Samardzija for free (to be flipped) at the cost of a few non-elite prospects. Alas, that deal also failed to pass due to financial considerations for the Giants involving other players.

I was heartened to see a few others buy into Chatwood’s rebound ability.

Around the time that the Chatwood deals began to fall apart, I made a breakthrough. One of the tricks of the Simulation is to find a player that somebody else really loves and seek value there. This often seems unrealistic, but there are plenty of real-world examples. Think Dave Stewart selling the farm to bring in Shelby Miller. Or Bill Bavasi falling in love with Erik Bedard and shipping out Adam Jones, Chris Tillman, and George Sherrill for him.

In my case, that player was Michael Rucker.

Arizona loved Rucker, seeing him as a Major League starter within a year. It’s not crazy given his meteoric rise from 11th-round pick to real prospect and Rucker just completed Double-A with eight strikeouts per nine and a WHIP of just 1.12.

I asked about two of my favorite Diamondbacks, and was pleasantly surprised to find that the offer from Arizona was Rucker for both: lefty Andrew Chafin and righty Archie Bradley. I snapped it up.


Transaction No. 1: Cubs trade right-hander Michael Rucker to Diamondbacks for left-hander Andrew Chafin and right-hander Archie Bradley

Chafin was one of my top three lefty reliever targets whereas Bradley fit into a big bunch of folks who could plausibly close but are best suited for setup work. They both fit swimmingly in the Cubs bullpen, and at a combined cost of $3.8 million via arbitration, they opened some possibilities.

Transaction No. 2: Cubs trade right-hander Brandon Kintzler to Twins for right-hander Jhoan Duran

Duran’s best-case scenario is that he turns into Kintzler in three years. But that didn’t matter: I wanted to (i) move Kintzler’s salary, and (ii) remove Kintzler’s memory from Cubs fans who couldn’t fathom how badly he struggled in blue pinstripes. This got done quickly after I went back to Minnesota.


Simultaneous with these trade discussions, I was negotiating with free agents. I targeted Harper and Machado for initial offers as well as Ian Kinsler, Jose Iglesias, and a bevy of relievers: Craig Kimbrel, Jesse Chavez, Jeurys Familia, Adam Ottavino, Andrew Miller, and Greg Holland. I also offered Garrett Richards a Smyly-style deal and sent minor-league offers to Jeff Mathis, AJ Ramos, and Logan Forsythe.

These approach to free agency showcased the parallel fronts of the Cubs offseason: if Harper or Machado might plausibly come to Chicago, they might open the checkbook in a big way. If not, they’ll likely dip their toes into the free agent waters but not much more than that.

Within 20 minutes of offering Harper $240 million over eight years, I was told that he had a 12-year, $400 million deal on the table. Well then. I dropped out on both big names...

But later that night, with the Chatwood talks progressing nicely, something happened: I heard murmurs from both San Francisco and Arizona that they were interested in Heyward. The returns would have been very low and I likely would need to include some cash, but after striking out in my conversations with Boston, Philadelphia, and the New York squads, I now had a viable path to clearing the space needed to sign Harper without screaming into the more onerous taxpayer penalties.

So I fired back: $420 million over 13 years with opt-outs after years three, six, and eight. If the Cubs do in fact sign Harper, I suspect that this will be the basic structure, though I’m not sure he’ll reach $420 million.

I also got bid up on Jose Iglesias to $5 million with $1 million in incentives before he accepted the offer.

Transaction No. 3: Cubs sign shortstop Jose Iglesias to a one-year, $5 million contract with up to $1 million in incentives

The Iglesias deal was key as he is the perfect defensive substitute/part-time starter to complement the middle infield with Russell removed. Speaking of, I floated Russell to the league and got serious interest from Toronto, Detroit, and San Diego. All three clubs were interested but didn’t want to pony up any type of premium for the troubled former star. In the end, that was okay by me as the clubs genuinely bid each other up from solid offers to this one:

Transaction No. 4: Cubs trade shortstop Addison Russell to Padres for right-hander Cal Quantrill and outfielder Edward Olivares

Olivares was a throw-in, a speed-first low-minors lottery ticket. But Quantrill. Oh baby, I love Quantrill. He had a rough 2018, but he comes with a tremendous, top-10 pedigree and could help the Cubs immediately. He was a perfect acquisition, the type of high-ceiling distressed asset that the Cubs might plausibly seek for Russell.

Shortly thereafter, the Red Sox decided that they had seen enough of Sandy Leon’s complete inability to hit in the Majors and non-tendered him. I was happy to save the day.

Transaction(s) No. 5: Cubs sign catcher Sandy Leon and second baseman Logan Forsythe to minor-league deals


The roster had largely taken shape at this point and it looked like the final outcome would be simple: either Harper signs with the Cubs for about $35 million per year and I trade Heyward, along with his right and center field defense, or he goes elsewhere and I keep Heyward, hoping for continued improvement with the bat while his plus glovework remains an asset.

That would’ve been a fine outcome, but writing out lineups left me with a problem that has been a problem for the last two years: who in the world starts things off? I’m a big fan of Ben Zobrist in the leadoff spot, but I’ll readily admit that there was one player who really caught my eye. Negotiations went remarkably quickly for such a risky transaction for both sides:

Transaction No. 6: Cubs trade outfielder Ian Happ, right-hander Cory Abbott, right-hander Jose Albertos, right-hander Oscar De La Cruz, and right-hander Tyler Chatwood to Royals for second baseman Whit Merrifield and right-hander Janser Lara

Before we proceed, please follow these steps:

  1. Take a big, deep breath.
  2. Take another big, deep breath.
  3. Go to Merrifield’s page on Fangraphs.
  4. Pick up you jaw from the floor.
  5. Look at Merrifield’s age.
  6. Realign your head from your confusion.
  7. One more big, deep breath.
  8. Read below.

Merrifield is the single most interesting trade asset in the game right now. He was a star in 2018 and an above-average regular in 2017. He led the American League in stolen bases in 2018 (45!). He plays good defense at second base and in center field. He hits for roughly average power. He isn’t even eligible for arbitration yet with just over two years of service time, giving his team four years of control. And despite his inflated .352 BABIP in 2018, it wasn’t that inflated: he routinely posts BABIPs around .330.

On the other hand, Merrifield turns 30 in January and isn’t yet eligible for arbitration. That’s alarming. Merrifield reached Triple-A in 2014 and simply couldn’t get out despite good production until late 2016. Merrifield’s power, while adequate, is not a meaningful asset. And a real chunk of his value in 2018 came from that .352 BABIP.

Merrifield is projected for a .274/.329/.405 batting line in 2019 along with 31 stolen bases and a dozen homers with good defense at both of the aforementioned spots. Put it all together and his projection calls for 2.7 WAR. That’s a really good player who just produced nearly double that in 2018 after a strong 2.9 in 2017.

The Royals originally asked for Happ, one of Alzolay or Miguel Amaya, and one of recent first-round pick Alex Lange, Albertos, or De La Cruz. Through negotiations, I dropped the Alzolay/Amaya piece to Abbott (who is a good prospect but not ready to help in 2019 and not a catcher!), and threw in two of the three pitchers from the last group in exchange for Lara and Kansas City absorbing all of Chatwood’s salary. Cubs fans should generally detest the team sending out prospects to shed salary, but in this case, I found this deal wise.

It’s possible that Happ alone is worth more than Merrifield, which would make this deal a real stinker. Unfortunately, between the strikeouts and inability to stick on the dirt defensively, it’s possible that Happ will be just a 1.5 to 2 WAR player. The extra win or so of jumping from Happ to Merrifield was worth the other pieces to me. But just as importantly, the fit of a player like Merrifield on a Cubs roster that needs to stop playing Happ in center, likely needs to spell Zobrist at second with regularity, and desperately has to find some speed kicks the value up in a big way.


Things were pretty well locked into place at this point as we headed to the penultimate day waiting for Machado and Harper. I continued poking around in trade discussions. A deal that the real Cubs would take but that I couldn’t quite do involved shipping Caratini to Oakland for injured righty James Kaprielian and recent comp pick shortstop Kevin Merell. I held out for glove-first shortstop Richie Martin as the secondary piece, even if I needed to add something for the A’s, but they used Martin more efficiently in another deal. That team has shortstops coming out of its ears.

I did sign a former A’s reliever that you’ll likely recognize:

Transaction No. 7: Cubs sign right-hander Jesse Chavez to a one-year, $4 million deal

Arguably the single most likely thing I accomplished.


Early in the afternoon, Machado signed with the Phillies for $433 million over 11 years with an opt-out after the fourth year, including a full no-trade clause. Even with regular Simulation inflation (about twenty percent), that raised an eyebrow or two. On one hand, it makes sense: Philly absolutely has to come away with one of Harper or Machado this winter. Their entire rebuild depends on it. On the other hand: dang.

I stayed in the Harper chase through the afternoon before it shot up to $485 million over 12 years. I contemplated whether there was a way to get to something like $500 million over 13 or even 14 years with opt-outs making the deal even more palatable, but I kept coming back to the same thing: if Harper costs the Cubs Bryant, Rizzo, or Baez, I’ll kick myself over it. I know that they need to win now more than they need to extend players in 2022 and beyond, but at some point, the Harper money gets so big that it doesn’t make sense. To me, $39.6 million per year has crossed that threshold, which is what Harper actually got: $515 million over 13 years from the Yankees with an opt-out after 2021. If that contract comes down the pike from the Yankees, he’ll be in pinstripes and not the Cubbie Blue variety.


To close out the simulation, I participated in a four-team trade that accomplished the following: the Twins acquired Gio Dingcong from the A’s, A’s acquired Lizardy Dicent from the Pirates, the Pirates acquired Edmond Americaan from the Cubs, and the Cubs acquired Kody Funderburk from the Twins. It was fully an excuse to write down those four glorious names.

I did try to find Duensing a new home, but instead he’ll come to camp to fight for a job as the Cubs prepare to vigorously employ the 10-day disabled list.


The final payroll and roster didn’t turn out exactly as I expected, but then again, it never does. Here are the payroll figures of the assembled 25-man roster* (there are too many guaranteed deals for a true 25-man roster, but you get the idea):

Catcher: $1.11 million ($1.11 million for luxury tax)

  • C Willson Contreras: $0.555 million
  • C Victor Caratini: $0.555 million

Infield: $48.7 million ($45.557 million for luxury tax)

  • 3B Kris Bryant: $12.4 million
  • 2B Ben Zobrist: $12 million ($14 million for luxury tax)
  • 1B Anthony Rizzo: $11 million ($5.857 million for luxury tax)
  • SS Javier Baez: $7.1 million
  • SS Jose Iglesias: $5 million
  • 2B Tommy La Stella: $1.2 million

Outfield: $24.21 million ($27.21 million for luxury tax)

  • OF Jason Heyward: $20 million ($23 million for luxury tax)
  • OF Kyle Schwarber: $3.1 million
  • OF Albert Almora: $0.555 million
  • OF Whit Merrifield: $0.555 million

Starting Pithcer: $83.1 million ($84.933 million for luxury tax)

  • LHP Jon Lester: $25 million ($25.833 million for luxury tax)
  • RHP Yu Darvish: $20 million ($21 million for luxury tax)
  • LHP Cole Hamels: $20 million
  • LHP Jose Quintana: $10.5 million
  • RHP Kyle Hendricks: $7.6 million

Bullpen: $37.45 million ($38.95 million for luxury tax)

  • RHP Brandon Morrow: $9 million ($10.5 million for luxury tax)
  • RHP Steve Cishek: $6.5 million
  • RHP Pedro Strop: $6.25 million
  • RHP Jesse Chavez: $4 million
  • LHP Brian Duensing: $3.5 million
  • LHP Mike Montgomery: $3 million
  • RHP Archie Bradley: $2 million
  • LHP Andrew Chafin: $1.8 million
  • RHP Carl Edwards Jr.: $1.4 million

Despite some big contracts, the Cubs offense remains on the cheap side for a major market team at $74.02 million. The pitching, however, breaks the bank, coming in at $120.55 million. Add it all up and the payroll hits $194.57 million. For luxury tax purposes, the payroll hits $210.76 million once the approximately $13 million worth of player benefits is added in.

That is an awfully interesting tally. The 2019 luxury tax threshold is $206 million. I figure that the Cubs will either exceed the threshold in a meaningful way, perhaps even nearing the enhanced penalties at the $226 million total, or they’ll try to stay below the $206 million tax line. However, it’s possible that they start the year in this space, climbing higher as necessary in July or working to drop back below the line if, heaven forbid, things go poorly in 2019.

The expected offensive lineups purchased by that amount are good. Really good. Enjoy!

Versus right-handed pitching

CF Merrifield
3B Bryant
1B Rizzo
SS Baez
LF Schwarber
RF Heyward
2B Zobrist
C Contreras

Versus left-handed pitching

LF Merrifield
3B Bryant
1B Rizzo
2B Baez
C Contreras
CF Almora
SS Iglesias
RF Zobrist

Finally, with the Steamer projections released within the past week, here is a look at the Cubs roster with WAR projections for 2019 and approximate playing time adjustments:

Bryant: 5.7
Rizzo: 4.2
Baez: 3.2
Schwarber: 2.9
Merrifield: 2.7
Contreras: 2.7
Zobrist: 2.5
Heyward: 2.4
Iglesias: 1.2
Almora: 1.1
Caratini: 0.7
La Stella: 0

Hendricks: 2.6
Darvish: 2.6
Quintana: 2.6
Hamels: 2.4
Lester: 2.0
Bradley: 0.7
Morrow: 0.7
Strop: 0.5
Chafin: 0.4
Edwards: 0.3
Montgomery: 0.3
Chavez: 0.1
Cishek: 0.1
Duensing: -0.1

In the end, the position players are projected for 29.3 WAR with an additional 15.2 WAR from the pitchers. That combined 44.5 WAR would rank sixth in MLB, narrowly ahead of the current projection for... the Chicago Cubs. How do you like that?

With another Simulation in the books, what do you think about this proposed version of the 2019 Cubs?