The most regrettable White Sox of the 2010s

First, a bit of unrelated news: The White Sox announced Dallas Keuchel this morning, filling the 40-man roster. A corresponding move will have to be made before Edwin Encarnación is official.

The contract differs a little from the original reporting. It’s indeed for three years and $55.5 million, and he’ll make an even $18 million per over those three years. However, the option is a club option for $20 million, not a vesting one, with a $1.5 million buyout if the White Sox decline to exercise it.

From the press release:

“We viewed Dallas as one of the premier free agent pitchers available this winter and so are thrilled to add him to this team and to our starting rotation,” said Rick Hahn, White Sox senior Vice President/general manager. “Dallas is a great competitor who we foresee throwing valuable innings in meaningful games for us over the next several years and leading our entire pitching staff through his example day in and day out.”

* * * * * * * * *

When mulling over the Most Forgettable White Sox of the 2010s, I debated whether that word could be stretched to include the ambitious sense of the term. Some fans, be they casual, late-arriving or maybe living off the grid for a year, might not have been aware that a certain underperforming player ever wore a White Sox uniform, and don’t we wish we were them?

But no, there seemed to be a clear line between forgettable and regrettable, and this team comprises the latter.

With the Most Forgettable and Most Regrettable teams stacked up against Josh’s All-Decade Team, the negatives are leading the positives 2-1. I’ll even the ledger before the year and decade come to a close.

Catcher: Dioner Navarro

  • Year: 2016
  • Line: .210/.267/.339 over 85 games

It’s well-worn territory that the White Sox briefly had a perfectly adequate catching platoon with Tyler Flowers and Alex Avila. Then they non-tendered Flowers to sign Navarro. Trading framing for Navarro’s kind of offense was a terrible idea from the start, but one of his better seasons might’ve led to an interesting philosophical discussion. Instead, Navarro ended up hitting worse than Flowers, too, making the whole thing moot (.210/.267/.339).

Honorable mention: Welington Castillo. It wasn’t a bad attempt to solve the catching problem at the onset, but his positive receiving year with Baltimore turned out to be an aberration, and he ended up earning the White Sox’s first in-season MLB substance suspension.

First base: Adam LaRoche

  • Years: 2015-16
  • Line: .207/.293/.350, -0.8 WAR over 127 games

Having just weathered the Adam Dunn experience, the White Sox rushed right back into locking their DH up with Washington’s former first basemen, and he proved to be an even worse idea. He was just as hard to watch at the plate, and making matters worse, his insistence on making his son part of the clubhouse, and the #FaithAndFamilyFirst firestorm that developed after he quit in protest, made headlines around the globe and set the tone for a disastrous last season of the first rebuild.

Honorable mention: Yonder Alonso, who hit worse than LaRoche, but owned a greater sense of awareness about his circumstances.

Second base: Gordon Beckham

  • Years: 2009-2015
  • Line: .242/.304/.370, 7.4 WAR over 839 G

Beckham delivered his only 2 WAR season in the previous decade. From 2010 to 2015, he was a below-average player who still played over 100 games every year, and perhaps a Beckham-less infield makes it easier to give Marcus Semien a shot. He did deliver Yency Almonte in a trade, which turned into Tommy Kahnle … before it turned into Blake Rutherford, resetting the circus of value.

Honorable mention: Brett Lawrie, who was a perfectly adequate veteran plug-in until orthotics ruined his career. Emphasis mine, because it doesn’t seem so simple.

Third base: Jeff Keppinger

  • Years: 2013-14
  • Line: .253/.283/.317, -1.9 WAR over 117 G

Keppinger joined the Sox to be a stopgap solution at third base, but he came to Chicago with a shoulder injury, failed to draw a walk over his first 141 plate appearances, and things never got better. The White Sox were so disenchanted with Keppinger that they cut him in the middle of his comeback attempt despite being owed $8.5 million over the final two years of his deal. He then lived out a midlife crisis on social media that ended with a racist tweet and a lamer excuse.

Honorable mention: Mark Teahen, whose acquisition would’ve been a decent, harmless idea had the White Sox not immediately extended him.

Shortstop: Ray Olmedo

  • Year: 2012
  • Line: .244/.244/.293, -0.1 WAR over 20 games.

Olmedo hadn’t appeared in an MLB game since 2007 before the White Sox came calling. They opened up the utility infielder spot when they traded Eduardo Escobar to the Twins for Francisco Liriano, and Olmedo proceeded to pack a lot of damage into 20 games. One game in particular stands out: When Robin Ventura benched Alexei Ramirez for showing up late, Olmedo batted second, committed an error, failed to run out a bunt attempt, then struck out to end the game (because he was batting second). He’s not forgettable to me because he scored on the Misfit Grand Slam.

Left field: Kosuke Fukudome

  • Year: 2012
  • Line: .171/.294/.195, -0.2 WAR over 24 G.

I almost put Fukudome on the Most Forgettable team over Lastings Milledge, but Fukudome actually signed a major league contract, albeit for just $1 million. Nobody had a good time, and the White Sox ended up designating him for assignment because they liked Jordan Danks more.

Center field: Jacob May

  • Year: 2017
  • Line: .056/.150/.056, -0.6 WAR over 42 PA.

May’s 2017 season was a lot like Daniel Palka’s 2019, except May had no other MLB success to point to as indicative of terrible luck. He just couldn’t hack it. He started his career going 0-for-26 before delivering a pinch-hit single, after which he let out an anguished scream.

He notched just one more hit before the White Sox demoted him in favor of Adam Engel, and May set the bar so low that Engel’s been allowed to accrue 1,047 plate appearances despite a 63 OPS+.

Right field: Jon Jay

  • Year: 2019
  • Line: .267/.311/.315, -0.8 WAR over 47 games.

Once the White Sox stopped short of signing Manny Machado, Jay was going to be seen as a vestigial organ. He lived down to that billing, missing most of the season with a vague hip injury, then missing whatever speed and power he had left when he finally showed up.

Designated hitter: Mark Kotsay

  • Year: 2009-10
  • Line: .252/.318/.391, -0.7 WAR over 147 games

I originally put Adam Dunn down, and maybe he should be since his historically awful season was at the center of so much strife in 2011. That said, Dunn might not even be part of White Sox plans if the White Sox didn’t dismiss Jim Thome and entrust the spot to Kotsay in 2010. The Sox then set the Peter Principle into action, as Kotsay went from being a decent bench bat to an awful primary DH (.239/.306/.376), while Thome helped save Minnesota’s season after Justin Morneau went down.

Honorable mention: Dunn hit .159 over 496 plate appearances.

Starting pitcher: Jeff Samardzija

  • Year: 2015
  • Line: 11-13, 4.96 ERA over 214 IP, 0.3 WAR

You’re probably thinking James Shields, but thanks to Semien’s MVP finish and Chris Bassitt’s successful rebound from Tommy John surgery, the Samardzija trade is even more difficult to rationalize. The White Sox traded four talents of note for one year of Samardzija, who was never going to sign an extension despite a hometown connection due to what he perceived his role to be for the union. The White Sox unveiled the “Shark Cage” promotion before he started first game (Opening Day, another weird thing), and Hawk Harrelson deemed him a “Captain of Attitude” for a team that didn’t go anywhere. Then Samardzija himself went elsewhere.

Honorable mention: Shields. Yes, he cost the White Sox a future star in Fernando Tatis Jr., but his third and final season in a White Sox uniform was more valuable than Samardzija’s only one.

Relief pitcher: Kelvin Herrera

  • Year: 2019-present
  • Line: 6.14 ERA over 57 G, -0.4 WAR

Herrera has one more guaranteed year to salvage his tenure in Chicago, but the first year saw the White Sox pay him $8.5 million for a glorified rehab stint. His ERA rose above 6.00 on May 25, and it stayed there over his final 36 appearances on the season. That doesn’t even include the 12 inherited runners he allowed to score, which is a remarkable number since he only had 19 of them all year.

Honorable mention: Scott Downs, who I once called Pajama Jeans for Men.

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Jim Margalus
Jim Margalus

Writing about the White Sox for a 16th season, first here, then at South Side Sox, and now here again. Let’s talk curling.

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I think you may be a bit of a White Sox masochist Jim. 🙂


“Circus of Value” sounds like a line from those old Swap-o-Rama flea market commercials and I think it’s perfectly apt here.

As Cirensica

How can I unread this?

Insert Homer’s GIF of pouring bleach on eyes


Shields easily has to be the most regrettable.

Imagine this same lineup with Tatis at short, Anderson in center, and Robert in right.

Not to mention he actively hurt their effort to keep their 2016 season afloat.


Thanks for that, Mr.  Wasn’t down enough on this Monday. 


100% its Shields in a landslide he culminates so many things the sox front office does wrong. Tack on his terrible performance, his still large (especially by sox standards ) salary, and of course the fact we gave up a future hall of famer for him.


*Might* be ever so slightly premature to be throwing around “future HOFer” talk.


Its premature, sure. But if you had to bet on who would be a HOF just based on their prospect pedigree and first MLB season, he would be at the top of your list. Highly elite prospect pedigree with outrageous physical tools playing the most premium defensive position on a diamond puts up a .970(!) OPS in his first season in flipping San Diego of all places.


The Shields and Samardzija trades are reasons   Why I was terrified of the David Price trade rumors 

Trooper Galactus

Well, unlike Shields, Price hasn’t necessarily lost his effectiveness, just his durability. Though it’s safe to assume a loss of durability foretells a loss of effectiveness.


If Tatis wasn’t traded, the Moncada trade would never have been made.


The forgettable lineup gave me a chuckle. This lineup made me want to vomit in terror. Having to choose between LaRoche and Yonder gave me voting booth flashbacks. 

Lurker Laura

I don’t think I will ever see the name Adam LacRoche and not recoil in disgust.

lil jimmy

LaRouche has my vote. What a smug douche.


LaRouche has my vote.

Chilling words in an election year.

Lurker Laura

Ha. Well done. When he died earlier this year, and I read his obit, I thought, “wow, I forgot what a nut job he was.”


With Ken Harrelson putting Carlton Fisk in left field and Lyndon LaRouche’s candidates for lt. governor and secretary of state winning the Democratic primaries, 1986 was a very weird year in Illinois.


Did Ted’s Sporcle this week inspire this post? Well done.

Keppinger is the only player I can recall the Sox cutting with multiple years left on a contract.

Trooper Galactus

I think Danks had more money left on his contract when he was cut, though not as much time remaining.


After reading the articles Most Forgettable and Most Regrettable White Sox of the 2010’s, I am amazed that there are still White Sox fans. I am even more amazed that the brain trust that brought the White Sox these distinguished characters are still employed in MLB.

Patrick Nolan

Thanks, I hate it.


I always considered the trade for Shields as the hanging offense for Hahn, but the trade for Samardzija may be more appropriate.

And is LaRoche still in the saving sex workers racket?

Eagle Bones

Hmmm someone is mistaken here. MLBTR is reporting as of this morning that Keuchel’s option is a vesting option that becomes a team option if it doesn’t vest (see below):

The Scott Boras client also has a fourth-year club/vesting option. Keuchel, the White Sox revealed, will earn $18MM annually, and the Sox hold a $1.5MM buyout on his 2023 option. His option will reportedly vest at $20MM if he pitches 160 innings in years two and three of the contract. Otherwise, it functions as a traditional club option.

Not saying you’re wrong Jim, but reporting on this option seems to have been all over the place from the start. The writeup on mirrors what you have here.


Shields was not “valuable” to the White Sox in any way, shape or form.

This list shows exactly why we haven’t had any winning seasons since Hahn took over as GM, or whatever his title is.

As Cirensica

Shield threw 200 innings of above replacement quality in his last year. That has value. As accentuated in prior year, it has more value that one might think.

John SF

Considering how desperately teams like the Angels needed pitching, and considering Shields was coming off an ~2 WAR season with 200-innings, why do you think he didn’t end up with an MLB contract last year?

I kind of have to assume it was Shield’s decision to hang it up after a semi-good year rather than risk retiring after another disaster year. I don’t remember seeing any stories or rumors about it last off season.


There was some reporting he wasn’t offered any deals worth taking. I imagine that at some point pride can outweigh the desire the keep playng. Knowing when to say when and all.

Trooper Galactus

That’s why Jermaine Dye didn’t play after 2009, and he was a borderline All-Star in the first half of that season (second half, obviously, was beyond awful).

John SF

he taught someone (Dunning? Cease?) a new curveball or changeup grip and technique that they really liked, and then had immediate good results with in the minors.

I can’t remember which Athletic Story it was in to look it up off the top of my head though.

Obviously nothing is ever going to outweigh what we lost in Tatis Jr. But maybe over the course of our 6 years with one of those pitchers, if that pitch is 10% better than it would have been, that could be worth a couple WAR. Mayyyyybe that pitch will be the strikeout pitch TO TATIS in Game 7 of a World Series against the Padres in 2023– and in the post game interview Dylan will give a big shout out to James Shields! Stranger things have happened in baseball.


I like this! You are very talented and should be working at a top PR firm with the ability to turn something so negative into a potential positive.


The Athletic Story you’re thinking of is “How James Shields is leaving a lasting mark on the White Sox rotation”.

He showed Dunning a Curveball grip in spring training and Dunning showed it to Cease.


More trades with the Cubs and Dbacks. Trading with Preller and Beane strictly prohibited.


Nothing like throwing up in your mouth for some Monday fun!

Trooper Galactus

Kinda surprising (and indicative of to what lows the White Sox were able to sink with some of their personnel) that John Danks and Ronald Belisario didn’t make the cut here. Danks’ extension after the 2011 season couldn’t have gone more horrifically between injury and ineffectiveness, though I have to admit I’m surprised they were even able to squeeze what little they got out of him since shoulder capsule surgery is typically the end of any pitcher (see: Santana, Johan). As for Belisario, $3 million for -1.6 bWAR just about says it all, and he posted a worse ERA+ than Herrera.

Papa Giorgio

*PTSD flashbacks of DHydra*