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Five Days As Theo & Jed: The Cubs In The 2015 SB Nation Offseason Simulation

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BCB joined 29 other fake GMs to simulate the offseason. Here's where the Cubs ended up.

Mark Kolbe/Getty Images

From last Saturday morning through Wednesday morning, I got to pretend to be Theo Epstein and Jed Hoyer, participating in the SB Nation Offseason Simulation project. As was the case last year, it was an absolute blast. As I told Al before Game 3 of the NLCS, I've been prepping for these five days for months, in part because I want to do a good job and in part because I want to be prepared for the real MLB offseason where names change hands in a flash.

This article walks you through the simulation process day by day, beginning with my pre-Simulation objectives and culminating with the snapshot of the fake Cubs system at the end of the winter. Here's the complete list of deals made during the simulation, via Royals Review, who hosted it.

Disclaimer: unlike last year, I did not trade Kris Bryant.

(Further disclaimer: if I could still get Chris Archer, Blake Snell, Archie Bradley, Braden Shipley, Richie Shaffer, Mike Montgomery, Ryne Stanek, Ryan Brett, and Justin Williams for Bryant and Pierce Johnson, I'd do it in a second)

With that out of the way, here's the Cubs diary from the 2015 Simulation. Enjoy!

I went through literally hundreds of different offseason plans. Unlike last year, this year was much easier as I determined that Bryant, Addison Russell, Anthony Rizzo, Kyle Schwarber, Jake Arrieta, and Jon Lester would not be moved under any circumstances and a handful of other players would only be moved in a ridiculous deal, including Hector Rondon, Javier Baez, and Kyle Hendricks. That kept things simple.

By Friday night, I was settled on the plan:

1. Sign David Price for up to eight years, $216 million, targeting a deal in the 7/$190 million neighborhood. Duh.

2. Target Austin Jackson, Jarrod Dyson, Dalton Pompey, Charlie Blackmon, Will Venable, Alejandro de Aza, or Rajai Davis to play center field for next year. A cheap, one-year option before Albert Almora and Eddy Julio Martinez come knocking.

3. Trade Chris Coghlan for the best value available. I love having Coghlan on the team both in the Simulation and in real life, but it's tough to see the Cubs bringing him back after he vented about his reduced role with both Schwarber and Soler in tow.

4. Trade Travis Wood for the best value available. Wood is a really nice reliever, and had my budget been more like the $140 million budget I expect the Cubs to have than the $131 million I had in the Simulation, I probably would have just kept him. Alas, $6.4 million was too much...depending on his market.

5. Trade Starlin Castro for best value available. I'm firmly in the camp that is ready to see Starlin head out, even if he doesn't return top dollar. His contract is definitely movable now whereas it wasn't in July. I fully recognize that unloading him could be a bad deal...but it could also be a great deal.

6. Explore deals for Jason Hammel. Hammel is a good value at $9 million next year, but I felt like I could have used that payroll space even more efficiently.

7. Scour the free agent marketplace for deals of any kind.

8. Beef up the bullpen with power arms.

9. Find reliable bench pieces, including an up-and-down starting pitcher with options remaining.

Over the last few months, I drafted 55 emails to initiate contact to the other general managers and with free agents. I was ready.

And we're off! Deals couldn't be officially consummated until Sunday night and free agent contact couldn't be made until Sunday night either, but that didn't keep Saturday from being a big day of wheeling and dealing. Of the four players I planned to move, only Wood had a robust market; I received silence on Castro, Coghlan, and Hammel, something that was genuinely surprising.

As was the case last November, some teams didn't really want to engage in serious dialogue and that was fine. Probably 10 of the 29 clubs basically stayed on the periphery.

Of the teams that did reply, they were universal in conveying that controllable pitching would be very expensive. This wasn't surprising, of course.

There was, however, very heavy interest in one Cubs prospect: Dan Vogelbach. We all know that Big Dan's raw power is through the roof, and we also know that the kid gets himself on base with the best of them. Unfortunately, those of us who have followed his development know that (1) he can't run, (2) he can't field, and (3) the prodigious power has remained largely of the batting practice variety. Nevertheless, unlike last year, I entered the Simulation with no intention of trading him. After a few teams bid up the price on him, it became clear to me that dealing Dan would be a great way to fill a couple of needs.

I went to bed on Saturday night with no agreements for deals. Strange.

Sunday was a different story. Early in the day, I negotiated the complementary piece in the Vogelbach deal with Colorado down in a significant way such that my first deal was done:

Transaction #1: Cubs trade 1B Dan Vogelbach and SP Ryan Williams to Rockies for CF Charlie Blackmon and SP Eddie Butler

Butler had been a target of mine given his tremendous arsenal, pedigree, and size. He's been terrible in the Majors, but he wouldn't be the first talented-but-scuffling arm to put it together after leaving Coors. Blackmon, however, was the real attraction as a first-year arbitration-eligible centerfielder slated to make $4.5 million. I've liked Blackmon for years, even amid concerns that his splits indicate he is a Coors mirage. He runs extremely well, I trust my eyes, and I'm betting that the BABIP-driven home/road splits will normalize around a 2 or so win player.

Conversations regarding Travis Wood's salary were advancing at this same time with both Cleveland and Minnesota in the picture. I was targeting Cleveland's trio of attractive, productive arms in Corey Kluber, Carlos Carrasco, and Danny Salazar as well as starter-turned-reliever Zach McAllister. They offered McAllister for Wood and Christian Villanueva, but in the end, I liked the depth of Minnesota's offer more:

Transaction #2: Cubs trade RP Travis Wood to Twins for RP J.T. Chargois, 3B Trey Cabbage, and RP Cam Booser

Chargois was the real draw. He's missed years with Tommy John surgery, but he was back with a vengeance in the fall of 2014 and he continued using his high-90s fastball to work through Double-A this year. He should be a bullpen option by mid-2016. Cabbage was the 110th pick in this year's draft where the Twins went about 50% over budget to get him signed. Booser is a big lefty with a mid-90s fastball that walks a lot of guys but strikes out way more. He's got LOOGY written all over him, as a floor anyway.

As I was close to closing the deal with Minnesota, I finally got two nibbles on Castro. The Mets poked around Starlin for a little while, but the Yankees expressed serious interest. With my desire to move Castro's money and add more impact talent to the system, regardless of level, the deal came together quickly:

Transaction #3: Cubs trade SS Starlin Castro to Yankees for SP Ian Clarkin, RP Jacob Lindgren, and OF Jose De Leon

This is easily one of my favorite moves of the Simulation. Clarkin, the 33rd pick in the 2013 draft, has been a favorite of mine for a while who was likely only available because of elbow soreness that kept him out for the 2015 regular season, though he has since returned to participate in the Arizona Fall League. The 22-year-old Lindgren zoomed through the Yankees system from the 2nd round of the 2014 draft, overwhelming Triple-A batters this year before holding his own in the Majors. He's a small lefty with a powerful two-pitch punch. I love him as a current bullpen piece. De Leon was the 2nd-ranked player in the 2014 International Free Agent class given his all-around profile with five tools that project as above-average or better. I think that this would actually be a strong template for a real-life Castro trade should the braintrust pursue such a deal, something I'd like to see.

Around this time, two rather significant developments occurred. First, the Padres indicated some very strong interest in Arismendy Alcantara. Having written this piece on Alcantara's implosion just last week, I saw an opportunity for a steal. Second, I heard back from my lowball initial offers to some free agents. My initial offer of $180 million over seven years to David Price was well received, but the stunner was that my offer of $50 million over four years for Jeff Samardzija got serious consideration. More on that in a bit.

The discussions with San Diego progressed quickly with me not wanting to risk that their general manager realized Alcantara's inability to recognize a changeup. We consummated a truly absurd deal in the Cubs' favor:

Transaction #4: Cubs trade 2B/OF Arismendy Alcantara to Padres for 2B Cory Spangenberg, CF Travis Jankowski, and SP Casey Kelly

Kelly is a flyer from the Red Sox/Padres regimes of year's past; the other two players were the keys. Spangenberg is a perfect reserve infielder and a great insurance policy for Baez at second base, not to mention that he was hand-picked by Jason McLeod. His speed-first profile and solid bat make him a great fit on the bench. Jankowski is a no-power, all-speed supplemental round pick from 2012. He hit .335 with a .413 on-base percentage between Double-A and Triple-A before making his MLB debut and he stole 32 bases in 97 games. He's the perfect reserve outfielder.

Right around the time of this trade, a big development broke on the trade market: the Marlins were blowing up their roster, including making Jose Fernandez available. I had the top offer on the board for much of the evening with Gleyber Torres, Ian Happ, Billy McKinney, Donnie Dewees, and Jen-Ho Tseng proposed in the deal for Fernandez and Marlins' closer A.J. Ramos.

Then Boston traded for Clint Frazier, paired Frazier with Yoan Moncada, and Fernandez was a Bostonian. I won't be surprised if something vaguely like this happens this winter.

I spent a few hours that night hammering out ideas for deals involving guys like Drew Smyly, Jake Odorizzi, Giancarlo Stanton, Jonathan Lucroy, and Tyson Ross in addition to attempting to gauge the market rate for players like Zack Wheeler, Byron Buxton, Andrew McCutchen, and Sonny Gray.

If there was a player to find, I found him and inquired.

Monday was the day that the Simulation jumped the shark. I spent a few hours in a tense negotiation with the Red Sox on David Price. We crossed the $200 million threshold rather quickly and when I added the eighth year at $220 million, I knew that I was in trouble. Thankfully, shortly before then, I got some really nice news on a free agent:

Transaction #5: Cubs sign SP Jeff Samardzija to a 5-year, $70 million deal

I know that some, and perhaps many, of you don't like the Shark. I look at him and see a No. 2 starter coming off of a dreadful year in which he was still sneaky productive with a realistic floor as a No. 4 starter who should age well. Do not underestimate the impact of the White Sox' porous defense; it made all of their pitchers look a lot worse than they really were. Tony Blengino over at Fangraphs addressed Samardzija last week and found that, well, he's still a good pitcher, even if he's not a great one. I expect that Samardzija will get a larger deal than this in the real world, so I was quite pleased to snag him.

Shortly after Samardzija signed, Scott Kazmir signed with the Diamondbacks for $64 million over four years, raising eyebrows. Then I got another piece of great news for filling out my roster:

Transaction #6: Cubs sign OF Will Venable to a 1-year, $2 million deal with a $3 million club option

I'm a Venable fan and this deal represented great value for a versatile reserve.

That sent me back to Price.  My final offer got to $234 million over eight years. Now, will David Price get close to that number? No. Not a chance. But that's irrelevant because I didn't get close to Price as he signed for $259 million over seven years with the Diamondbacks. This was the first instance in which I asked aloud whether any of these folks have ever watched baseball.

I reeled for a bit from the Price news, but then I remembered that this happened last year, too. Many team budgets don't reflect reality, leaving the marketplace flush with hundreds of millions of dollars of cash that don't enter the real baseball marketplace which results in deals like the Price contract.

I did get another piece of good news after the Price deal exploded:

Transaction #7: Cubs trade OF Donnie Dewees to Marlins for RP Carter Capps and RP Michael Mader

Dewees has some value as a long-range prospect for the Cubs, but even with his late-season elbow scare, Capps is far too valuable to pass up here, especially given his $800,000 salary next year. Mader is a LOOGY in the making with a lively fastball.

Around this time, I circled back with the free agent outfield targets that I had only to find that their markets were otherworldly. I made a strong seven-year, $136 million offer to Jason Heyward...who subsequently returned to St. Louis on an 11-year, $310 million deal that included an opt-out too! Sweet sassy molassey.

That deal was only a bit crazier than Dexter Fowler's six-year, $106 million pact.

Fortunately for me, while other teams were out spending their cash on wildly-overpriced free agents, my newfound financial flexibility empowered me to capitalize on a rival with payroll issues:

Transaction #8: Cubs trade SP Felix Pena and RP Yoervis Medina to Pirates for RP Mark Melancon

Will Melancon make $10 million in his final arbitration year in 2016? Yes. Does he give me the best bullpen in baseball? Yes. Does he help suppress Rondon's arbitration earnings? Yes. Might he come with a qualifying offer next winter? Maybe. And did he cost me two guys who weren't going to be on the 40-man roster in two weeks? Yup!

I spent the evening discussing Drew Smyly trades with the Rays and then engaging the Braves in talks for Shelby Miller and Julio Teheran. I'm not a Teheran fan, but the Braves set a good price on Miller and wouldn't budge. I respected their style even though I think Miller is an excellent Cubs target.

I was encouraged that I somehow carried the high offer on Austin Jackson at one year for $3 million into Monday evening...before the Phillies swooped in and gave him $25 million over two years.

As the night ended, the only real question outstanding was one that I suspect Jed Hoyer will face in a month or so: should I trade Jorge Soler in a deal for a non-ace starting pitcher? My swings on Soler have been violent. On the one hand, he's (1) constantly injured, (2) much slower than expected, (3) a very poor defender, and (4) coming off of a first half where he struggled mightily at the plate. On the other hand, he's got (1) amazing power, (2) strong discipline, (3) unbelievable ability to drive the ball, and (4) a line of .292/.381/.510 over the last three months that suggests that he's ready to be an offensive force despite his shortcomings elsewhere. (BCB's own Josh Timmers addressed many of these issues on Tuesday if you'd like to continue feeling conflicted.)

I engaged in discussions with clubs about Soler, but I remained on the fence about dealing him, setting a very high price tag and sticking to it.

As Zack Greinke got $210 million to cover his age-32 through age-38 season and Justin Upton snagged $230 million, I kept my focus on trade possibilities. The Rays clearly didn't align with me in their valuation of Soler but they still wanted him, something that caused us all to bang our heads against the wall repeatedly.

The Padres, on the other hand, clearly valued Soler highly and they seemed as least mostly receptive to my positioning of Soler as a Rizzo-esque bat in right field; naturally, I didn't mention the health or fielding concerns. We toyed with numerous iterations of the deal, but in the end, I got my home run for the rotation once the Padres were able to unload a big chunk of Matt Kemp's deal elsewhere:

Transaction #9: Cubs trade RF Jorge Soler and SP Eric Jokisch to Padres for SP Tyson Ross, SS Jose Rondon, SP Austin Smith, and SP Jose Castillo

Easily my favorite trade. Ross maxed out my budget, but it's worth it for such a dynamic arm in his prime. Rondon is a solid Double-A shortstop with a pedigree, Smith is a 2015 2nd-rounder with a huge arm, and Castillo was a raw $1.55 million bonus baby from the 2012 international market with a strong lefty profile. The depth pieces were strong and the headliner is a great #2. The culmination of days of groundwork.

In the end, I feel as though I added an incredible amount of value to the club while the one true core piece that I dealt away -- Soler -- is the most easily replaceable from within the system as Coghlan and Venable can handle the right field job in 2016 with McKinney, Mark Zagunis, and even Ian Happ zooming toward Wrigley Field in the not-too-distant future.

Here is the final roster by position group and ordered by 2016 salary within each group:

Starting Pitchers

Name 2016 Salary Final Year of Team Control
Lester, Jon $20,000,000 2020 (2021 club option)
Samardzija, Jeff $14,000,000 2020
Arrieta, Jake $10,600,000 2017
Ross, Tyson $10,000,000 2017
Hammel, Jason $9,000,000 2016 (2017 club option)
Hendricks, Kyle $508,000 2020
Butler, Eddie $508,000 2021

Relief Pitchers

Name 2016 Salary Final Year of Team Control
Melancon, Mark $10,000,000 2016
Rondon, Hector $3,600,000 2018
Strop, Pedro $4,700,000 2017
Richard, Clayton $1,100,000 2016
Grimm, Justin $1,000,000 2019
Capps, Carter $800,000 2018
Ramirez, Neil $508,000 2020
Edwards, C.J. $508,000 2021
Lindgren, Jacob $508,000 2021


Name 2016 Salary Final Year of Team Control
Montero, Miguel $14,000,000 2017
Ross, David $2,250,000 2016


Name 2016 Salary Final Year of Team Control
Rizzo, Anthony $5,000,000 2019 (2020, 2021 club options)
Russell, Addison $508,000 2021
Bryant, Kris $508,000 2021
Baez, Javier $508,000 2021
Spangenberg, Cory $508,000 2020
La Stella, Tommy $508,000 2020


Name 2016 Salary Final Year of Team Control
Blackmon, Charlie $4,500,000 2018
Coghlan, Chris $3,900,000 2016
Venable, Will $2,000,000 2016 (2017 club option)
Schwarber, Kyle $508,000 2021
Szczur, Matt $508,000 2021
Jankowski, Travis $508,000 2021

The final cost for the 25-man roster plus $11.6 million of dead money owed to Edwin Jackson and Gerardo Concepcion was $132.114 million, a tiny bit above my stated $131 million budget.

As the tables above indicate, one of the primary appeals of this club is the presence of such tremendous, controllable depth. The chart does not indicate the minor league free agents I procured during the Simulation, including Nate McLouth, David DeJesus, Burke Badenhop, and Ryan Cook.

Somewhat strangely, the infield depth chart is actually the weakest link on the roster. The Cubs could choose to option La Stella to Iowa to make room for Christian Villanueva such that Villanueva wouldn't need to be non-tendered. But that's a bit on the nitpicky side considering that both Spangenberg and La Stella are young, starting-caliber reserves.

In the end, I had mixed feelings about dealing Soler, but the opportunity to snag the six-man rotation of Arrieta-Lester-Ross-Samardzija-Hendricks-Hammel just proved too appealing, especially when the Padres met my prospect demands. The nine-man bullpen is also built to absorb regression and injuries. It's hard to imagine how daunting it would be to see Grimm enter in the fifth inning only to know that you'd have to force extra innings to get past Capps, Strop, Rondon, and Melancon. Yikes.

I particularly loved adding so much talent with future value grades of 50 (or better). I was floored that, for all of my moves, I only surrendered three of the Cubs' top 30 prospects according to Dewees (8th), Vogelbach (13th), and Ryan Williams (30th) while adding at least six new members (Ian Clarkin, Jose Rondon, Austin Smith, Travis Jankowski, Jacob Lindgren, and J.T. Chargois)  in addition to four new fringe top-30 players, three of which come with significant ceilings (Jose De Leon, Trey Cabbage, Jose Castillo, Michael Mader).

I really enjoyed myself these last few days, even if it took a lot out of me. It's fun to imagine how the offseason might play out, but it's infinitely more enjoyable to actually simulate the whole thing.

So there you have it. Your fake 2016 Chicago Cubs, comprised of nine transactions over the course of five days. I imagine that the "regular" lineup would look something like this:

CF Blackmon
LF Schwarber
3B Bryant
1B Rizzo
SS Russell
RF Coghlan
C   Montero
2B Baez

What do you like? What do you dislike? Which moves would you do? Which ones would you avoid and why? Have at it!