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Shadow White Sox: A simulated rebuild

Can the White Sox do what their northern neighbors did last year?

MLB: Kansas City Royals at Chicago White Sox Matt Marton-USA TODAY Sports

Brock Osweiler looks like a combination of your standard high school jock and said jock twenty years later, working late hours as an investment broker whose favorite string of words is ‘back in high school.’ Brock Osweiler plays football like he is being controlled by your drunk cousin John in a game of Madden he probably shouldn’t have started in the first place.

In 2016, the Houston Texans decided to sign Osweiler to a hefty, four-year, $72 million contract that went south in the sort of accelerated slow motion sadness that you see on pitchers’ faces as they miss a spot down the middle to Giancarlo Stanton, or that you feel happening on your own face as you knock your iPhone into the toilet bowl.

But where other teams pointed and laughed at the hapless, flailing Texans who pants’d themselves so hard that said pants zipped into another dimension, the Cleveland Browns saw an opportunity. Houston desperately wanted to rid themselves of their error, and Cleveland was willing to take on the entirety of the contract and had the cap space to do it. Houston paid the Browns with a second round draft pick. The Browns cut Osweiler before the 2017 season. It didn’t matter; they already acquired what they wanted.

Imitating the Cleveland Browns is usually a shortcut to disastrous folly, but in this instance their idea was brilliant, even if the execution was lacking. They Browns sucked. They knew they were going to continue to suck. They had a bunch of cap space. But they could continue to accrue prospects by leveraging that cap space into draft picks and youngsters, as ‘for free’ as you can get whilst spending millions of dollars.

It was this approach that I took to the Chicago White Sox in guiding them through the 2017 SB Nation offseason simulation. Chicago, as a team, is bad. It will continue to be bad until 2020 or so, when its ridiculous farm system will hopefully begin to propel the White Sox to glory, just like the Kansas City Royals in 2015, the Chicago Cubs in 2016, and the Houston Astros in 2017.

So with a huge chunk of payroll available to me, I Browns’d it up. The 2018 Shadow White Sox will feature a quintet of somewhat broken, expensive veterans. But alongside those veterans came a cavalcade of prospects to fill depth in an already excellent farm system.

I’m honestly not sure there’s ever been an MLB team that has executed this particular strategy this intently in real life—Houston certainly could have in their rebuild, as the Other Chicago team could have—so this is a really interesting experiment.

To begin with, let’s look at the raw transactions that happened.


  • Royals trade Ian Kennedy, Josh Staumont and $16 million to the White Sox for Chris Beck
  • Marlins trade Wei-Yin Chen, Brayan Hernandez, Merandy Gonzalez, and Edward Cabrera to the White Sox for Jordan Guerrero and $4 million
  • White Sox trade Nate Jones to the Athletics for Dakota Chalmers
  • The Orioles trade Mark Trumbo, Mike Yastrzemski, Brandon Barker to the White Sox for Ian Clarkin
  • Mets trade Dominic Smith, Jordan Humphreys, and Gavin Cecchini to the White Sox for Jose Abreu.
  • White Sox trade Avisail Garcia to Blue Jays for Sean Reid-Foley and Justin Maese
  • Rockies trade Adam Ottavino and Forrest Wall to the White Sox for Jake Petricka and Zach Putnam and $4 million
  • Braves trade Matt Kemp, Freddy Tarnok and Kyle Muller to the White Sox for Matt Cooper

Alright! Let’s get more granular and focus on the guys themselves.

Filler Traded

  • Matt Cooper
  • Ian Clarkin
  • Jordan Guerrero
  • Chris Beck

Max, the Shadow MLB Commissioner, disallowed trades for straight-up cash or players to be named later. So this quartet got the axe out of necessity, as the named players on some of these lopsided deals.

You won’t miss any of them. Such is the life of a prospect. Not all succeed.

Non-Filler Traded

  • Jose Abreu
  • Avisail Garcia
  • Jake Petricka
  • Zach Putnam
  • Nate Jones

The awkward part about rebuilding is that having good players when you’re bad actually hurts your team. All five of these guys had more value as trade chips than White Sox. None of them were going to be efficient impact guys in 2020 or beyond.

Garcia is the most interesting of the five. He had a breakout season in 2017, but one that was out of nowhere. It’s also a breakout that isn’t sustainable—Garcia posted a sky-high BABIP of .392, walked at just a tick below 6% of the time, and posted a significantly above average baserunning score for the first time in his entire career. There’s about 1500 plate appearances that say Garcia is a replacement-level talent, and only 561 that say otherwise. Cashing in on a player at their peak is always the smart move for a rebuilding team.

Vets Acquired

  • Ian Kennedy
  • Wei-Yin Chen
  • Mark Trumbo
  • Matt Kemp
  • Adam Ottavino

Ian Kennedy was a replacement level starter last year. Matt Kemp was below replacement level, as was Mark Trumbo. Both are slotted as starters in the outfield, which is going to be so hilariously porous that a slice of Swiss cheese will look like Fort Knox by comparison.

Adam Ottavino was also replacement level last year, but he was pitching in the launching pad that is Coors Field and has otherwise been a cromulent reliever in prior years. Wei-Yin Chen’s contract is gigantic, and he’s struggled to remain on the field since signing the deal; Chen only has 156 innings to his name over the previous two seasons.

Now, Chen might turn out alright. If he bounces back from his last two injured seasons to full health, he should be an effective pitcher—he was so when he was on the field—and that means that he could be exchanged for prospects sometime down the line. The same could theoretically be true for the others as well.

But you know what? These five are the White Sox’ Brock Osweilers. This team is going to be terrible for two years. If the White Sox want to cut bait on any of these players, especially if a prospect comes up to take their place, they can go for it.

Incoming Prospects

  • Josh Staumont RHP / 23 / AAA / KCR 9
  • Brayan Hernandez OF / 19 / A- / MIA 8
  • Merandy Gonzalez RHP / 21 / A+ / MIA 6
  • Dakota Chalmers RHP / 21 / A / OAK 18
  • Mike Yastrzemski OF / 27 / AAA / BAL Unranked
  • Brandon Barker RHP / 24/ AAA / BAL Unranked
  • Dominic Smith 1B / 22 / MLB / NYM
  • Jordan Humphreys RHP / 21 / A+ / NYM 13
  • Gavin Cecchini IF / 23 / MLB / NYM 8
  • Sean Reid-Foley RHP / 21 / AA / TOR 6
  • Justin Maese RHP / 20 / A / TOR 14
  • Forrest Wall OF / 21 / A+ / COL 11
  • Freddy Tarnok RHP / 18 / RK / ATL 26
  • Kyle Muller LHP / 20 / RK / ATL 12

This list includes the player’s position, age as of now, highest level achieved, and the prospect ranking of what team they were coming from per MLB Pipeline.

You’ll notice that there aren’t any top-five guys anywhere. That’s mostly due to how they were acquired; nobody’s sending their organization’s best prospect in a salary dump. The one guy who made Baseball America’s midseason Top 100 prospect list—that’d be Smith, at 50—was the cornerstone of a trade that involved an actually productive MLBer (Jose Abreu).

Rather, it’s the sheer amount of B-/C+ prospects that is important. Nine of these guys were in their organization’s top fifteen prospects (ten if you include Smith, who is ineligible because of the amount of games played in New York this year). Yastrzemski and Barker were blocked guys by Baltimore and will get Major League experience this year; if they turn out to be AAAA fodder, they were AAAA fodder acquired for nothing. And of the pitchers, multiple throw easily in the upper 90s.

So what does the heckin’ 2017 White Sox team look like?

Position Players

  • C Omar Navarez
  • 1B Dominic Smith
  • 2B Gavin Cecchini
  • 3B Yoan Moncada
  • SS Tim Anderson
  • RF Matt Kemp
  • CF Adam Engel
  • LF Mark Trumbo
  • DH Nick Delmonico

Starting Pitchers

  • Wei-Yin Chen
  • Ian Kennedy
  • James Shields
  • Dylan Covey
  • Lucas Giolito

Relief Pitchers

  • Adam Ottavino
  • Kyle Kendrick
  • Chris Beck
  • Greg Infante
  • Aaron Bummer
  • Juan Minaya
  • Michael Ynoa


  • Leury Garcia
  • Kevan Smith
  • Tyler Saladino
  • Yolmer Sanchez

Look at that infield—every one of those dudes is 25 or under, every one under team control through 2022, including Navarez. Yeah, you could squabble with Moncada at third base, but he’s played the hot corner before and Cecchini doesn’t have the arm for it, so there’s no real downside at the moment.

What you should not do is look at the outfield. Jesus. It’s so bad. Kemp’s career DRS in right field and left field in 5500 innings is -63. Trumbo, in 3000 innings in right and left, sits at -29 DRS. Thank the Baseball Gods that they can DH in order to mitigate the disaster.

Starting pitching is similarly disturbing, although a Chen/Kennedy/Shields triumvirate is not likely to stay healthy the whole year, clearing its own way for younger starters. And the relief core can be built from the collection of White Sox talent that’s already there.

Things that almost happened

Since this was a simulation and not a real thing with real consequences, we can talk about the behind the scenes stuff. So here are some things that almost happened; some are good and some are bad.

  • Bud Norris and Kyle Gibson signings

I didn’t really emphasize free agency, as it didn’t net me prospects. I was interested in expanding pitching and grabbing guys who could be flipped at the deadline should they succeed. Both of these would have qualified, but I just missed on both. I actually outbid for Gibson—he had signed minutes before my escalated offer—and Norris’ agent ignored my questions regarding whether or not he needed an MLB offer or not.

Before Abreu headed to the Big Apple, I had a deal almost in place with Cleveland. Cleveland’s GM was considering the above deal when they traded Bradley, tossing the discussion in disarray without its central piece, and then won the bidding for Carlos Santana, thus removing their need for a first baseman like Abreu.

  • Trade discussions about Yasmany Tomas, Chris Davis, and Shin-Soo Choo

Word got around that I was interested in taking on salary for prospects, and I was in discussions for a number of players. The three above were the most-discussed guys for whom a trade never materialized. I balked on Davis, but discussions there led to the acquisition of Trumbo.

  • Last-minute acquisition of Nick Markakis

The Tampa Bay Rays and Houston Astros were engaged in eleventh hour trade discussions, and needed a third team to take on some salary. That salary being Markakis. After feeling out what kind of prospect they’d send my way, I declined to grease the wheels of that trade.

But can you imagine? A Trumbo/Kemp/Markakis outfield? Great balls of fire and brimstone, that would be apocalyptic. Demons sprouting from the ground like weeds. Wolves and sheep living together and then ripping each other apart. A ball falling between a sprinting Kemp and Trumbo that Lorenzo Cain could have caught at walking speed. Oof.