Captain Wookie's Offseason Plan

All In 2: Electric Boogaloo

To start off I created two offseason plans, one more reasonable than the other. This is the Kenny Williams variant, and I'll probably post the reasonable one in the comments. They were both fun to construct in very different ways. This one is crazy by nature and full blown CrazyTown BananaPants at times so it will fit in with some of these. There’s bound to be some flags and some serious concerns, lord know I have them and I assembled this monstrosity. Also Here’s the Hail Mary . . .


Tender all of them except for Jennings. The prices given are good for the value they are bringing to the ball club. I’ve gone back and forth on tendering Jennings a few times but in the end he’s not going to help or hurt us. Tyler Flowers is not the biggest problem this team has, more on that coming up.

Contract options (pick up or buy out)

The decline in 2014 has me a bit worried. Not picking up the option. I would actively try and resign him to a lower dollar figure that Nine Million, because while he still may have something still left in the tank I would not pay Nine Million for it. There’s something that is plan shaped below (and I use that term loosely).

Impending free agents (re-sign, let go, or qualifying offer?):

Offer Samardzija the QO and hope he rejects it. Matt Albers was good in the roll the team had him in this season when he was healthy. I think he will get better offers than what the White Sox will offer and what I would offer, so let go. Buy Gordon Beckham a one way bus pass to 1260 South Main Avenue Fallbrook, CA 92028 to learn the fine Avocado business from the best and never let him darken this team again. I ultimately decided to let Soto go, as I don’t think he would resign with the White Sox as there will be more money and playing time elsewhere.

Free Agents

The velocity and strikeouts are down and that worries me a bit. Overall still a good starting pitcher and like Shark will probably get lost in the noise of the bigger starting pitchers in the free agent market. Still not a bad option and can be plugged in near the top of the rotation and and is right handed (for those that actually care about the handedness of the rotation). Contract breakdown $19, $21, $23, $26, $25, $24

This is also assuming he doesn’t hang it up this year. Seven million sounds like a good number for him near the end of his career who can still give up 200 innings or pretty dang close to it. And let’s face it, it’s going to happen whether we write about it or not.

I used the Zach Duke contract as a reference here. Pretty good against lefties and not awful against righties. A good lefty to take the place of Dan Jennings in the bullpen. Contract breakdown $4, $5, $5

  • Jason Heyward for 8 years, $211 Million with an opt-out clause after the fourth year

I will openly admit I am ball parking the contract; however it’s a pretty safe bet that there’s going to be at least 7 years, 9 digits, and an opt-out clause. He is going to be 26 years old next season and I know I used some fuzzy math on the last half of the contract as I don’t honestly expect him to be around that long. He will be 30 going into the opt-out and he would make another gigantic pile of money on FA Market, so assuming no catastrophic injuries it would only really be a 4 year deal. And with this we get a a hitter near the top of the order and some fantastic defense in the corner outfield spots. And with how the outfield defense looked this past season I think we all can agree this would be a welcome change. Contract breakdown $20, $25, $28, $28, $28, $28, $30, $30, & $32.


Let’s not kid ourselves, the White Sox need catching depth and a potential upgrade. Flowers is a good catcher but there is an opportunity to get a good one who is currently very blocked. The Giants need pitching and we need catching. Both sides win.

I’m reminded of the (not really) immortal words of Calculon when I look at this roster and depth chart. The only way I really can sum it up is as BAD. The Ryan Braun contract is pretty awful and we have a serious need for right handed power in this lineup. The Money breakdown is $4 million/year covering part of Braun's contract through his guaranteed years. Due to the entire Danks and LaRoche contracts being here there we would cover half remainder of difference between what Braun makes versus what Danks and LaRoche make, which comes to $4.375 million I don’t think Adam Lind will be on the Brewers next year so there will be probably be an opening at 1B. Looking at the rest of their roster is just painful. Micah (if healthy) and Webb should have very few issues making the opening day roster here. John Danks, while overpriced, would still be an upgrade on the horrendous starting pitching they have.

Alright folks, time to get on your BananaPants! I don’t want to trade any of our core, I really don’t. But Quintana has a lot of trade value and if I had to assess (which is kinda the idea behind this) he would be the one I would be the most comfortable with trading away. In terms of improvement, we will get the most for our assets (money or players) at upgrading the black hole of awful that is 3B. Is it a lot to give up, yes. Is it likely to get done, I have some doubts but I don’t think it’s an awful starting point.

The Rockies took on the Reyes contract on to get top prospects in the trade with the Blue Jays, and their yearly budget is not very friendly towards it. If we even want to have a realistic chance of landing Arenado, Reyes and his contract will probably need to end up on the table. Arenado is lining up for a substantial payday and will price himself out of the Rockies liking sooner than later (arb 1, likely super 2 and is already at $6.6 million). I also don’t think the CarGo will be on their opening day roster. Any deal involving Arenado with the White Sox is going to start with Sale or Quintana, that’s just the nature of it and they need pitching. They also have put a premium on hard throwing pitchers, much like Montas who also fills a need on the team. So Rockies get one top of the order SP with a good ground ball rate, a potential SP or high leverage bullpen arm, a good pitcher in the minors, an outfielder with potential that could really put it together out in Colorado, and financial relief. White Sox get a 3B that they can be proud of for the first time since Joe Crede, a stopgap at SS to be moved to 2B when Tim Anderson is ready, and depending on how much money we end up taking hopefully a starting pitcher. I added Eddie Butler as more of a starting point to level the trade out a bit, Butler is more of a pipe dream but I would seek a SP from some level to even it out a bit more.

My 25 Man Roster and Starting Lineup

  1. Adam Eaton - CF
  2. Jason Heyward - LF
  3. Jose Abreu - 1B
  4. Melky Cabrera - DH
  5. Ryan Braun - LF
  6. Nolan Arenado - 3B
  7. Jose Reyes - SS
  8. Tyler Flowers - C
  9. Carlos Sanchez - 2B
  1. Andrew Susac - C
  2. Mike Olt - CI
  3. Tyler Saladino - INF
  4. Trayce Thompson - OF
  1. Chris Sale
  2. Jordan Zimmermann
  3. Carlos Rodon
  4. Mark Buerhle
  5. Eddie Butler
  1. David Robertson
  2. Zach Duke
  3. Nate Jones
  4. Jake Petricka
  5. Antonio Bastardo
  6. Zach Putnam
  7. Scott Carroll


I’ve done some awful things to the original budget figure and to the pitching depth near the major league roster. This is where I draw issue with the three year plan that was brought up earlier in the season. There are a lot of holes in the roster going into the off season and this addresses a lot of them while simultaneous depleting some of our more useful resources and getting rid of some not so useful parts. In the end if we are trying to compete, the team needs act like it and pony up to catch the other teams in the division. The Royals are back in the World Series for the second straight year and the Twins are getting even better. The wild card race isn't much better when you look at some of the other teams around the AL. This team has significantly upgraded its power and defense, somethings that is important when half your games are played in a stadium very friendly to power hitters. With the players acquired having Tyler Flowers and Carlos Sanchez occupying the bottom two spots in the batting order is far from the worst thing ever. Is it worth the dramatic increase in payroll? Only time would be able to tell on that; I know I could have worked a few of the deals to get more money off in the trades and structure the contacts a lot better considering the payroll go up a bit next year by a few million. The final payroll figure is using the 2015 season figure for player minimum salary ($507,500) and this season's shouldn't be that far off.

2016 Projected Payroll


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