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SB Nation Offseason Simulation: Cubs Deals And Signings

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30 teams, 30 fake GMs, Three days. Go!

David Banks

Thanks to Al, I had the chance to participate in SB Nation's mock offseason over three days at the beginning of this week. It was a blast. I spent a few weeks preparing for it, putting together in upwards of 50 different 40-man rosters. The payrolls and the 25-man roster constructions fit together in almost endless ways.

For this exercise, each team was represented by a General Manager. We were given a recommended budget and we had 65 hours to complete the offseason: negotiating with and signing Major League free agents, executing trades, determining contract options, tendering or non-tendering controllable players, and managing the budget while doing so.

I entered the offseason seeking two pieces and two pieces alone: two mid-to-high-end starting pitchers. In my preparation, I made a list of 24 young, controllable starters to target in trade discussions including the likes of Danny Salazar, Sonny Gray, and Michael Wacha. I also prioritized the free agent targets, naturally listing Max Scherzer, Jon Lester, and James Shields at the top. I tentatively earmarked $47 million for making a run at two free agent starters out of my total budget of $98 million. I assumed that this would be plenty. Then again, free agency can be a fickle beast.

I also wanted to try to find a taker for Edwin Jackson, not because I personally believe that the Cubs must do so, but because I think that they will try in reality. Finally, as always, I was on the lookout for value.

With the stage set, here is something of a diary that runs through my experience, dissects the completed moves and those that died with only an "i" to dot and a "t" to cross, and gives my overall takeaway on the 2015 (and beyond) Cubs that I built.

The Three Days Prior to the Formal Kickoff of the Offseason
As someone who was completely ready for this, the three days before the formal open of business was the best. I contacted every team within a couple of hours to discuss Edwin or their young talent. Two teams that I expected to be contenders for one of my shortstops -- the Mets and the Marlins -- showed absolutely no interest whatsoever.

The biggest surprise of this period was that the Yankees showed tremendous interest in Justin Ruggiano. Also, I aggressively pursued deals for Edwin Jackson, and the Royals proved to be a willing dance partner. I had resolved prior to the simulation that I would eat $6 million of Edwin's salary to give him away for free. That's not how it went down.

The Yankees' pursuit of Ruggiano proved aggressive, and we rather quickly agreed to a deal in which I would send Ruggiano and Mike Olt to the Bombers for reserve catcher JR Murphy, former top pitching prospect Manny Banuelos, and 2012 top pick righty Ty Hensley. I assumed that Olt would be designated for assignment, so I really liked this deal. Within a day of agreement -- recall that no deal could be finalized yet -- the Yankees backed out, pulling Banuelos for use in another deal. I threw a fit, threatened to sabotage their GM, and he made an even better offer to save face, leading to our first deal:

Transaction #1
Cubs trade 3B Mike Olt to Yankees for C JR Murphy, SP Ty Hensley, and RP Adam Warren

Olt for Murphy is a win, Olt for Warren is a win, and Olt for Hensley is only a tiny loss. Olt for all three? I was ecstatic.

Around the same time, I resolved to add Luis Valbuena to my deal with the Royals in order to up the return. Kansas City added my sweetener piece and we had a deal:

Transaction #2
Cubs trade SP Edwin Jackson, 3B Luis Valbuena, $4 million in 2015, and $2 million in 2016 to Royals for SP Jason Vargas, SP Christian Binford, and SP Cody Reed

Binford has been a favorite of mine for a while, Reed is a huge lefty with a huge arm, and Vargas is a steady back-end starter. In my mind, I got all three for Valbuena seeing as I would have eaten the $6M to punt Edwin. I was feeling fine.

Philadelphia inquired on Cole Hamels for prospects, though they "only" asked for Arismendy Alcantara, Dan Vogelbach, and Zac Rosscup. I actually thought about it.

Day One
We completed the trades listed above. My goal in the simulation was to track the Cubs' offseason as realistically as possible, so I came in high on Tsuyoshi Wada:

Transaction #3
Cubs sign SP Tsuyoshi Wada for one year, $4 million

Before I made my final decision not to tender Travis Wood a contract and to decline Kyuji Fujikawa's $5.5 million club option, I offered the pair around the league. Fujikawa's market was cold, but San Francisco offered a penny or so for Kyuji. Hey, better than nothing:

Transaction #4
Cubs trade RP Kyuji Fujikawa to Giants for RP Stephen Johnson

Wood had quite a few nibbles, though few teams were willing to commit his hefty salary to a rebound candidate. Thankfully, the Yankees needed a starter, so they bit:

Transaction #5
Cubs trade SP Travis Wood to Yankees for IF Jose Pirela and SP Brady Lail

I had been interested in Lail, a low-level lefty, in the earlier trade. Pirela, however, was the big get. He should be my utility infielder for a couple of years on a minimum deal. Nice.

With my small work out of the way, I engaged the big fish. I found their markets to be...interesting. I contacted Lester, Scherzer, and Shields within a minute of free agency opening. I could tell that I had good traction with Shields. I offered four guaranteed years with a fifth year vesting option to bring the deal to $90 million total right away. I offered Lester five years, $126 million right away with an option that pushed it to $140 million over six years. I offered Scherzer $150 million guaranteed over six years or $168 million over seven years with an exercised option. I felt great about my huge, aggressive offers. I also aggressively pursued Brandon McCarthy along with Boston; we both ended up at $42 million over three years, but my offer required an easily vesting option to get there, so he went to Beantown.

Day Two
I had a number of teams ask me about my shortstops, and a team or two even asked about Kris Bryant. But free agency drove this day.

I'll cut to the chase. Lester signed for seven years, $192 million with Milwaukee. I just couldn't go there. Within an hour, I had my veteran starter:

Transaction #6
Cubs sign SP James Shields for four guaranteed years for $76 million with a vesting option for year five at $19 million more.

I felt great about it. I felt even better when I heard that Scherzer was up to $190 million over six years. At that point, my pursuit of elite starters was done.

I checked in on the secondary market as well, but prices remained goofy. Justin Masterson is terrifying to me even on a flyer deal: when a two-pitch pitchers loses three miles per hour on both of his pitches in one year, something is terribly, structurally wrong. Masterson got three guaranteed years for $30 million. No way.

I continued gauging the market for free agent values, and one email returned some promising news: David Robertson had no market. None. I offered three guaranteed years at $30 million with two $10 million club options thereafter. With my second-round pick already surrendered for signing Shields, the cost of Robertson was lower. Plus, I recalled an excellent piece in the Hardball Times detailing the cost savings in Oakland when the A's signed Grant Balfour, depressing the arbitration salaries of their other relievers like Ryan Cook. The Balfour signing played a large role in Sean Doolittle's deal being so obscenely club friendly. I thought of Hector Rondon, Neil Ramirez, and Pedro Strop, loving the idea of depressing their save totals to keep their salaries lower.

I recognized my need for a leadoff hitter and Joe Maddon favorite, so I swung the following deal:

Transaction # 7
Cubs trade CF Albert Almora and 1B Dan Vogelbach to Rays for 2B Ben Zobrist and SP Taylor Guerrieri

Late on Day Two, everything changed with two emails. First, Washington got a new GM. I had made some headway on a deal involving Starlin Castro and Gio Gonzalez with the previous GM, but the new guy wasn't interested. He was, however, interested in a pricey deal for Javier Baez. We exchanged a number of proposals, things got quiet for a bit, and then late in the evening, he agreed to the following proposal: SS Javier Baez, SP Jason Vargas, and RP Corey Black for SP Gio Gonzalez, SP A.J. Cole, OF Michael Taylor, SP Daniel Norris, and SS Franklin Barreto.

I loved that deal. Loved it. Gio is signed for $35 million over three years or $47 million over four years if his option vests. Cole is MLB-ready, Taylor and Norris have already made their MLB debuts, and Barreto was the top international signee a couple of years ago. Unfortunately, the Toronto portion of the deal fell through. We played around with some more ideas, but nothing came to fruition.

However, the second email became the driving force of my efforts for the remainder of the simulation. Arizona's GM emailed proposing a one-for-one swap of Kris Bryant and Paul Goldschmidt. While I recognize Goldshmidt as a superstar -- 27 years old, MVP runner-up in 2013, even better in 2014 until hand injury, and signed for just $43 million over five years -- I wasn't punting on Bryant, so I replied "only if your throw in Archie Bradley and Braden Shipley." He countered asking me to add Pierce Johnson and said we had a deal.

I was floored. I didn't know what to say for hours. I had to sleep on it.

Day Three
Scherzer closed his deal with Oakland for $200 million over six years; I actually laughed out loud.

But I was focused on Goldschmidt and the young arms. Arizona and I agreed to the following deal on a contingent basis after I realized that Dallas Beeler would have to be outrighted:

Proposed Transaction
Cubs trade 3B Kris Bryant, SP Pierce Johnson, and SP Dallas Beeler to Diamondbacks for 1B Paul Goldschmidt, SP Archie Bradley, SP Braden Shipley, and OF Justin Wiliams

It was just too much value. I've seen Pierce throw about 40 innings over the past two years, enough to know that the changeup isn't arriving anytime soon. Two premium pitching prospects, a low-level riser, and an MVP runner-up? It was too much.

But it was contingent: I needed to find a home for Goldschmidt.

I had three primary possibilities, although I tried others like the Pirates and Twins to no avail. I contacted the Nationals, Rays, and Red Sox, three teams with cheap, premium assets and a need at first. Washington was ready to move on to Chase Utley to complete their offseason. Still, we briefly discussed Goldschmidt for Gonzalez, Kyle Zimmer, Cole, Taylor, and Hunter Dozier.

In the meantime, it became clear that I was Robertson's primary suitor so I pushed for an answer and scored the deal:

Transaction #8
Cubs sign RP David Robertson for $30 million over three years with a fourth year $10 million club option ($1 million buyout) and a fifth year $10 million club option ($0.5 million buyout)

Back to Goldschmidt, Tampa Bay wasn't up to snuff with their offers. But basically the moment Boston found out about Goldschmidt's availability, I could sense that they were giddy. Boston's initial offer was the best offer I received and I wished I would have taken it before the day was through: Goldschmidt and SP Dan Straily to the Red Sox for SP Nathan Eovaldi, 3B Garin Cecchini, OF Rusney Castillo, SP Henry Owens, SP Trey Ball, and 2B Wendell Rijo. Instead, we haggled a bit over the fifth and sixth pieces of the deal. Over an hour or so, Boston's octoGM (they had eight people) got cold feet, particularly with regard to Castillo, and they pulled out. I continually attempted to reengage them, but they rebuffed my efforts.

Then, incredibly, they picked up both SP Kyle Crick and Salazar for pennies on the dollar. I re-engaged them given their newfound depth, and I even brokered a deal with San Diego that would ship Mike Napoli to the Padres with C Reese McGuire, SP Casey Kelly, 1B Adam Lind, and SP Jeferson Mejia heading to Boston with me keeping SP Matt Wisler as a commission. The deal was almost too good for Boston: compared to their initial offer, they shed salary, picked up three additional prospects, and the drop from Napoli's value to Lind's is only about 1.0 WAR anyway. The Boston GM needed the night to think...

Day Four
I awoke to yet another moment of complete and utter despair: Boston was out. They wanted to maintain their flexibility and depth...or so they said. Over the course of the next few hours, the Red Sox swung an 8-for-2 deal to acquire OF Giancarlo Stanton as well as a last-minute deal for Reds SP Mat Latos. There goes the depth!

But my despair didn't last for long. Unsolicited, Tampa Bay made an additional offer: Goldschmidt, SP Eric Jokisch, and RP Justin Grimm for SP Chris Archer, SP Enny Romero, C Jose Molina, 2B Ryan Brett, SP Ryne Stanek, SP Mike Montgomery, and SP Nolan Gannon. I was intrigued. I had no idea who Gannon was -- and it's really tough for me not to know someone who is at least on the prospect radar -- and I had no desire for Molina with Welington Castillo, Murphy, and Kyle Schwarber in the fold. I asked for a better prospect than the combined value of Gannon and Molina. He offered a guy in their 20-25 range. I wasn't interested.

And then payroll flexibility reared its beautiful head. The Rays were close to their budgeted amount with another hole or two to fill. I was solidly short of my budget, even with dead money for Edwin and Vargas' new contract. As such, I proposed taking on Grant Balfour's $7.5 million salary in exchange for better prospects, specifically SP Blake Snell and 3B Richie Shaffer. The chance to get out from Balfour's contract was too much, so Tampa took the deal:

Transaction #9
Cubs trade 1B Paul Goldschmidt, SP Eric Jokisch, and RP Justin Grimm to Rays for SP Chris Archer, SP Enny Romero, 2B Ryan Brett, SP Ryne Stanek, SP Mike Montgomery, RP Grant Balfour, SP Blake Snell, and 3B Richie Shaffer

The number of current or former top prospects was staggering.

And Archer. The prodigal son come home. Archer may have the best non-rookie contract in baseball: $42.25 million over the next seven years, his peak years. It's a marvelous deal.

With only a couple of hours left at this point, I scrounged the marketplace for free agent values. I signed 2B Gordon Beckham and SS Ramon Santiago to minor league deals. With only about $2 million left in the budget, I figured I was done.

Then Minnesota sent out a distress signal about SP Mike Pelfrey's contract: they needed to clear his $5.5 million salary. I offered to clear half by sending SP Felix Doubront and OF Ryan Sweeney to Minnesota for Pelfrey and a prospect. They offered their 30th ranked prospect; I replied asking for a back-end top-ten guy. After about an hour, they caved on the top-ten player and I had this deal:

Transaction #10
Cubs trade SP Felix Doubront and OF Ryan Sweeney to Twins for SP Mike Pelfrey and 2B/OF Eddie Rosario

Picking up Rosario was great, especially for my eighth starter (Doubront) and my sixth outfielder, also shedding Sweeney's $0.5 million 2016 buyout in the process.

But I wasn't quite done yet. I was looking at a rotation with Jake Arrieta, Shields, Archer, Wada, and Jacob Turner with Kyle Hendricks also fighting for the fifth spot. As such, Vargas already found himself on the outside looking in. Standing next to Archie Bradley, it didn't look good for Vargas. I checked in with five teams holding payroll space and needing a starter, and the Angels jumped, leading to the following deal:

Transaction #11
Cubs trade SP Jason Vargas to Angels for 2B Alex Yarbrough and OF Natanael Delgado

Delgado has massive upside, but he's a teenager. Yarbrough is a depth piece. But shedding Vargas' $8.5 million salary was worth it.

In the end, it's difficult not to think about what might have been had I executed the initial Red Sox offer, thus converting Bryant, Johnson, Beeler, and Straily into Bradley, Shipley, Castillo, Eovaldi, Owens, Cecchini, Ball, and Rijo. But that's not what happened. Instead, the Tampa deal won by default, loaded up the farm even more substantially, and left me with the following team:

Opening Day Lineup
2B Zobrist
SS Castro
1B Rizzo
RF Soler
3B Baez
CF Alcantara
LF Coghlan/Ruggiano
C   Castillo

Opening Day Bench
C   Murphy
IF Pirela
IF Watkins
OF Coghlan/Ruggiano
OF Watkins

Starting Rotation
SP Arrieta
SP Shields
SP Archer
SP Wada
SP Hendricks

RP Robertson
RP Rondon
RP Ramirez
RP Balfour
RP Wright
RP Warren
RP Turner

That roster came in about $7 million below budget. Just as importantly, it is slated to be cheaper with only simple replacements in 2016 and much better thanks to the arrivals of Addison Russell and possibly Kyle Schwarber. There will be oodles of cash to spend on the likes of Justin Upton or Jason Heyward.

So there you have it. That's what we came up with. What do you think? Love it? Hate it? Confused by it? Fire away. I can take it.

Notable Free Agent Contracts
I though you might enjoy seeing the deals handed out to the biggest free agents. This includes everyone who received at least $4 million guaranteed:

SP Max Scherzer: 6 years, $200 million with two options up to $57 million
SP Jon Lester: 7 years, $192 million plus a $20 million vesting option
SS Hanley Ramirez: 5 years, $130 million
OF Yasmany Tomas: 8 years, $128 million
3B Pablo Sandoval: 6 years, $100 million
SP James Shields: 4 years, $76 million plus a $19 million vesting option
3B Chase Headley: 4 years, $70 million plus a $17.5 million vesting option
OF Nick Markakis: 4 years, $62 million
C   Russell Martin: 4 years, $60 million
IF Jose Fernandez: 6 years, $80 million
SP Kenta Maeda: 5 years, $60 million
DH Victor Martinez: 4 years, $50 million
SP Jason Hammel: 4 years, $48 million
RP Andrew Miller: 4 years, $45 million
RP David Robertson: 3 years, $31 million plus two $10 million club options ($1.5 million buyouts)
OF Nelson Cruz: 2 years, $36 million plus $15 million vesting option or $10 million club option
OF Melky Cabrera: 4 years, $40 million
SP Chihiro Kaneko: 4 years, $40 million
SP Brandon McCarthy: 3 years, $42 million
SP Ervin Santana: 3 years, $40 million
SP Francisco Liriano: 3 years, $36 million
SP Jake Peavy: 2 years, $26 million
SP Justin Masterson: 3 years, $30 million plus $12 million mutual option
OF Mike Morse: 3 years, $30 million
OF Michael Cuddyer: 2 years, $22 million
OF Colby Rasmus: 2 years, $22 million
SS Jed Lowrie: 3 years, $24 million plus $8 million club option ($3 million buyout)
RP Rafael Soriano: 2 years, $20 million
RP Koji Uehara: 2 years, $18 million
SP Edinson Volquez: 2 years, $15 million plus a $10 million club option ($2.0 million buyout)
SP Kwan-Hyun Kim: 6 years, $29 million plus two club options
SS Asdrubal Cabrera: 3 years, $21 million
RP Luke Gregerson: 3 years, $18 million
SP Brett Anderson: 2 years, $15 million
RP Kris Medlen: 2 years, $12 million plus $8 million club option ($1 million buyout)
OF Nori Aoki: 3 years, $18 million
1B Adam LaRoche: 1 year, $12 million
IF Jhung-Ho Kang: 4 years, $20 million
RP Casey Janssen: 3 years, $15 million
RP Sergio Romo: 2 years, $12 million
2B Darwin Barney: 2 years, $10 million (really)
RP Brandon Morrow: 2 years, $10 million
OF Torii Hunter: 1 year, $8 million
IF Emilio Bonifacio: 3 years, $10.5 million plus $5 million club option ($1.5 million buyout)
RP Luke Hochevar: 3 years, $10 million plus $4.5 million club option ($2.0 million buyout)
RP Zack Duke: 3 years, $10 million
OF Ichiro Suzuki: 1 year, $7 million
SP Ryan Vogelsong: 1 year, $7 million
RP Pat Neshek: 2 years, $8.5 million
2B Rickie Weeks: 1 year, $5 million plus $7 million club option ($1.0 million buyout)
SP Chad Billingsley: 1 year, $5 million plus $4 million in incentives
1B Billy Butler: 1 year, $6 million
SP Gavin Floyd: 1 year, $5.5 million
2B Hector Olivera: 3 years, $9 million
RP Mike Adams: 1 year, $4 million plus $5 million club option ($1.5 million buyout)
SS Stephen Drew: 1 year, $4 million
RP Jesse Crain: 1 year, $4 million
OF Alex Rios: 1 year, $4 million
RP Tom Gorzelanny: 2 years, $6 million
RP Francisco Rodriguez: 2 years, $6 million
SP Kyle Kendrick: 2 years, $5 million
RP Joba Chamberlain: 3 years, $7 million
RP Jason Frasor: 3 years, $6.5 million
RP Joe Beimel: 2 years, $4 million
RP Joel Peralta: 2 years, $4 million