What if the White Sox front office was actually good?

Clearly no front office gets every move right every time.  While we have much to celebrate, including two straight playoff appearances for the first time in team history, today’s team could have been so much more.  This is my attempt to describe how strong the Sox would be today if eight decisions were made differently over the past eight years.  That’s only one change per year on average.  I’ll start with one of the most obvious moves we would like a do over on.

December 9, 2014:  Not trading Marcus Semien, Chris Bassitt, Josh Phegley, and Rangel Ravelo for Jeff Samardzija and Michael Ynoa

We gave up two future All-Stars and a backup catcher for one year of Samardzija and a lottery ticket reliever. I think it’s fair to say that the 2014 team was not one starting pitcher away from contending. With a 73-89 record and a fourth-place finish, the front office was kidding themselves with this deal. Needless to say, Samardzija’s 2015 season was a disaster. Despite adding Samardzija as well as Melky Cabrera, David Robertson, and Adam LaRoche in free agency, the Sox only improved by three games to 76-86 in 2015.

2015 MLB Draft: Drafting Walker Buehler at 8 instead of Carson Fulmer

This one admittedly might be a bit of a stretch. Fulmer clearly was more dominant statistically at Vanderbilt than his rotation mate. However, there were concerns about his size and high-effort delivery which would have made Buehler the safer pick. Fulmer was rushed to the big leagues and was never given the chance to develop properly. Buehler is a two time all-star with the Dodgers who has a career ERA of 2.90.

June 4, 2016: Not trading Erik Johnson and Fernando Tatis Jr. for James Shields and cash

This is of course the worst trade in White Sox history. Our Brock for Broglio, our Kenny-always-gets-his-guy nightmare. Shields was bad in pitcher-friendly SD in 2015 (4.45 FIP). He was also bad with SD to start 2016 (4.44 FIP). Yet the front office decided that after an underwhelming 29-27 start that was only good for third place, they had to have Shields. He rewarded that faith by posting a 4-12 record with a 6.77 ERA with the Sox who went on to finish 78-84 and in 4th place. Tatis, while apparently injury prone, has had two top-five MVP seasons before his 23rd birthday.

2016 MLB Draft: Drafting Will Smith at 10 instead of Zack Collins

Let’s get this out of the way: Zack Collins is not a catcher. He’s not a catcher now, he was not a catcher when he was with the White Sox, he will never be a catcher. Wishing he would be a catcher does not make it so. Unfortunately, despite a hot start this year with Toronto, he doesn’t appear to be a hitter either. Will Smith, on the other hand, is both a catcher and a hitter. He has a career .880 OPS and destroys right handed pitching to the tune of a .935 career OPS. Sounds like someone we could use.

2016 MLB Draft: Drafting Dane Dunning at 26 instead of Zack Burdi

Watching my older son graduate from Downers Grove South High School last weekend reminded me that I was ecstatic to see fellow Mustang Zack Burdi get drafted by my favorite team. Then I saw that he was a reliever. Wait, what?!? Chosen only three picks later was Dane Dunning, who had at least started 20 games for Florida in his collegiate career. Of course, we still picked him up in the Adam Eaton trade, so what’s the difference?  In this version of events, Washington picked Dakota Hudson at 29 (Hudson went to St. Louis at 34 in reality) and we ended up with Hudson as the third piece in the Eaton trade.

2018 MLB Draft:  Drafting Jonathan India at 4 instead of Nick Madrigal

Like the Burdi selection, this is a move I loved at the time. We drafted a scrappy, contact oriented infielder who never strikes out. His game reminded me of how my younger son plays the game and I thought he would man second base on the South Side for the next 10 years.  Oops. India was drafted by the Reds with the very next pick, and he went on to be named the 2021 NL Rookie of the Year. Oh, and he plays second base. Had the Sox made India the pick, there is no Madrigal injury and therefore no Craig Kimbrel trade. Of course that means that there would be no A.J. Pollock trade either, so who would be our right fielder today?

February 28, 2019:  Signing Bryce Harper instead of allowing him to sign with Philadelphia

While the front office appeared to be desperate to sign Manny Machado using the friends-and-family approach, the real jewel of the 2018-2019 offseason was Harper.  His signing fills the RF void definitively for the next 13 years. In the first four years of the contract, his OPS was no lower than .882. Last year he was the NL MVP with a league leading 1.044 OPS, and he drew 100 walks in 141 games.

October 29, 2020:  Bruce Bochy named White Sox manager instead of Tony LaRussa

Bochy won three championships in five years with the Giants, and had only sat out the 2020 season, so he was not out of touch with today’s game. There was also rumored interest on both sides, but we’ll never know if he would have been the choice had JR not interfered. With Bochy at the helm, Leury Garcia doesn’t receive more plate appearances than Andrew Vaughn and inexplicable Sunday lineups aren’t a thing.

What does this multiverse of madness style scenario result in? The short answer is that they would have had the kind of depth that they have never had in recent memory. Let’s take a quick look year by year.


Very similar results except with Semien at 3B instead of Gordon Beckham and Tyler Saladino.  The team would have received similar or better results from Erik Johnson, Hector Noesi, and Chris Bassitt as they did from Samardzija.


Again, very similar results, but with Semien showing progress at 3B the Todd Frazier trade never happens, resulting in Frankie Montas continuing his development in the White Sox system instead of with the Dodgers. Semien rewards the team’s patience by breaking out to the tune of 27 HR and a .735 OPS. With the Shields trade also not happening, Mat Latos gets a longer leash and delivers results that are similar to those Shields gave us in real life. Since the rotation is a mess, taking Dunning over Burdi in the draft is even more logical.


Rebuild 2.0 goes according to real life, with the exception of the Eaton trade. Instead, the Nationals get their championship RF by trading us Lucas Giolito, Reynaldo Lopez, and Dakota Hudson.  Otherwise, the team again has a similar record to their real life 67-95 result.


Things are starting to get interesting here. Walker Buehler starts 23 games with a 2.62 ERA and gets a top 5 finish in AL ROY voting. Dakota Hudson also has a strong callup pitching out of the bullpen, with a 2.63 ERA over 26 appearances. Chris Bassitt starts 7 games with a 3.02 ERA.  Marcus Semien steps back a bit but still contributes a .706 OPS. Frankie Montas starts 11 games with a 3.88 ERA. The starts fill the void created by not having Shields, and Dylan Covey doesn’t have to start 21 games as well. Despite the budding progress, the win loss record doesn’t improve significantly due to a poor offense, causing the front office to make a bold move.


Signing Harper to the largest contract by far in White Sox history is controversial, but it pays immediate dividends as the Sox form a suddenly impressive batting order. Yoan Moncada flipped positions with Semien resulting in breakout years for both. A team which in real life had five players who exceeded 100 OPS+ now has eight. The lineup of Anderson, Moncada, Abreu, Harper, Tatis, Semien, Jimenez, McCann, and Engel becomes one of the most feared in MLB.  On the pitching side, there is no need to trade for Ivan Nova, as the rotation now boasts Buehler, Giolito, Hudson, Bassitt, and Montas with Lopez and Cease as depth. I’d bet that this team surprises by getting into the playoffs and perhaps even making a deep run.


The money has already been spent, but that’s OK. With the pitching depth discussed above, there’s no need for Dallas Keuchel. Will Smith made his successful debut backing up James McCann and is ready to take over the starting job so Yasmani Grandal is also unnecessary. Luis Robert replaces Engel in CF. The Sox have arrived as a legitimate contender with World Series aspirations. Bassitt joins Buehler and Giolito as legit aces, and while Montas takes a step back Cease and Dane Dunning join the mix. Playoffs? Without a doubt. This team likely beats out the Rays to challenge the Dodgers for the best record in baseball and another deep playoff run seems inevitable, perhaps even a championship.


Adding the AL ROY in India to replace a disappointing Semien doesn’t seem fair to a lineup that’s flat-out ridiculous. There’s no need to sign Adam Eaton, or make a desperate trade for Craig Kimbrel because this team is absolutely stacked, both on offense and on the mound.  Harper wins MVP and Tatis leads the league in HR. Walker has a top 5 Cy Young year, Giolito and Bassitt also get CY votes, and Montas rebounds. They run away with the division and would likely win it all.


The loss of Tatis due to injury is a big blow after also losing Semien and Leury Garcia to free agency, but Andrew Vaughn can take over the DH spot so the lineup is still Anderson, Moncada, Abreu, Harper, Robert, Jimenez, Vaughn, Smith, and India with Gavin Sheets able to step in as DH to allow Vaughn to replace Jimenez due to injury. The rotation of Buehler, Giolito, Bassitt, Montas, and Cease with Hudson and Kopech in reserve is an embarrassment of riches. With Bochy pulling all the right strings, another World Series title is expected.

2023 and beyond:

This is what sustained success truly looks like when the goal is a World Series trophy, not just being competitive in the division and hoping to catch fire at the right time. Getting lucky is not a valid plan for long term success. This team has an amazing amount of pitching so they can absorb the potential loss of Bassitt after 2022 and Giolito and Montas after 2023. The lineup is also solid 1-9 with younger starters at catcher and second base than we have today.

While I’ve used hindsight to highlight these 8 moves that the Sox got wrong, the front office has also made many good moves, notably the Sale, Eaton, and Quintana trades. However, with the team struggling to stay above .500 when they should be running away with the division tells me that our chance at another parade may have already been blown. I believe this shows how those eight wrong choices impacted the team’s chance for championships, not just playoff competitiveness.  White Sox fans deserve the best front office in baseball.  Failing that, I would settle for a competent and accountable front office where performance and not tenure dictates positions. Thanks for reading, and go Sox!

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Fantastic piece – thanks for putting so much time & effort into this analysis.

It would be interesting to go through this and count the extra comp picks we could have if we had followed this path and made the appropriate QOs. Because one other thing that we stink at is accumulating talent. We went through the whole rebuild without really buying any prospects from teams that needed salary relief, we hang onto guys for depth who aren’t really very important (see, e.g. Mendick and Romy Gonzalez), and probably should have extended a QO to Rodon.


Enjoyed reading this!

Right Size Wrong Shape

I didn’t. It was a good article, though.


Yeah, I guess you don’t enjoy reading Jim’s writing most days, most years 😛

As Cirensica

I enjoyed and cried (figuratively) at the same time.


The 2016 Sox may have been 29-27 at the time of the Shields trade, but they got off to a 24-12 start. That led to some unrealistc talk of the team’s chances and then a desperate move when things were going south. If that team had started closer to .500, that trade doesn’t happen.

I like Bochy but question whether he really would have been interested after retiring from the Giants.

I have been following India a bit because I wondered about that move as well.

Nice analysis

Last edited 6 months ago by metasox

Very entertaining thought experiment. It’s possible we could have done something interesting by firing Ventura sooner and getting managerial competency prior to the Renteria move.


Thoughtful article. One “what could have been” that nobody talks about is how close the Sox were to signing Juan Soto. It sounds like the Sox had made the highest offer to Soto until the Nats beat it. So they were pretty close to getting him as well.

They need to poach some player development or scouting people from the Dodgers, seriously. The Dodgers have won 90 games each of the past 8 years, and have not had a top 20 pick in a decade. And yet somehow have the 5th ranked farm system. Obviously their people are at another level.

Asking the question “what if the Sox front office was actually good”. I think the answer is along the lines of “if my aunt had balls, she’d be my uncle.” This whole organization needs to be blown up from the top down. I wish Reindorf would show some dignity and class and sell the damn team.


” I wish Reindorf would show some dignity and class”

I believe this would be termed, alternate reality.


That was fun, thanks, appreciate all the effort and thought that went into it.


Very interesting (and much appreciated) analysis. I think that one might go back over 20 years, though, to the start of the KW era. I started to dread any major trade or acquisition. The Todd Richie trade back in December 2001 was a perfect example, though it was outdone by the similar Shields trade years later. These hobbled the franchise for a few years, both in terms of the ability to spend otherwise and by “forcing” us to use the acquired players. In contrast, the trades that set up the 2005 championship were much lower cost and less risk.


The history of effective baseball organizations (most business organizations, for that matter) is that ownership creates a clear hierarchy, hires competent management and gets out of the way. Does this sound like the WS?

Reinsdorf is who he is; a loyal, apparently decent man who does not see potential value in long-term contracts with high-end talent. He values friendship to a fault. In his mid-80s, it’s not likely he will make a 180 any time soon. It’s clear that he alone made the TLR choice, severely limited the pursuit of long-term studs and almost certainly influences other personnel decisions.

Kenny has a long history of valuing veterans over younger players. When you can identify value in veterans who are not washed up, that’s OK. When you cannot, and you continue to acquire bargain vets who have no value at all, then this strategy is worse than none at all. The last decade trades for vets generally have Kenny’s handprints on them. Someone else on this post suggested it; apparently the WS pro scouting dept. is not good at identifying talent that is not near the end. As illustrated by the lead article, they also struggle to consistently draft well. The WS were one of the last teams to modernize their scouting (as well as a lot of other areas – see Cooper et al), I suspect these two go hand in hand.

Hahn is the nominal GM. As such he should have primary, if not sole, authority over managerial personnel and player acquisition. Clearly he does not. He appears to have some skills, evidenced by the Big Three trades and contract extensions to younger potential stars. My suspicion is that the WS would be in a better place today if he were allowed to do his job unfettered by the wisdom of JR, Kenny or TLR.

TLR is a different issue. He is obviously the choice of no one except JR. Different opinions exist, my personal view is that he is a disastrous choice, unable to break the mold of his previous successful stints as manager to match up with changes in the game. He has long worshipped at the alter of a strong relief corps, my strong suspicion is that he was an influencer in the acquisition of multi-relievers at the expense of a better 2b and RF. Speaking of 2b, he also appears to treat Leury as a beloved grandson, and I have no doubt he influenced that extension as well.

I believe that this disjointed approach to decision-making has led to the conundrum the WS find themselves in today, and lacking a change in hierarchical philosophy, it’s not likely to change.


“… he is; a loyal, apparently decent man who does not see potential value in long-term contracts with high-end talent. He values friendship to a fault.”

This is a somewhat contradictory statement when taken in the context of his job responsibilities. A decent man wouldn’t be so overwhelmingly selfish and self centered as to value his personal relationship with individuals over the hundreds of thousands of fans that make his life possible.

A decent man wouldn’t give his middle finger to all those people in favor of getting what he wants out of it.


I assume you’ve met people in your life that are quite contradictory in their approach to certain issues. As the owner, he can do that without fear for his job status. That doesn’t make him a bad person.


People with as much money as Jerry has, and that hoard almost all of it, don’t make the world a better place.


It does make him tone deaf however and that usually doesn’t go hand in hand with, decent person.


I would love to be able to point the blame in one direction but let’s face it, I think the blame is a circle. You start with JR for undermining Hahn. So Hahn tries his best to put a good team together with the constraints of money and probably JR butting in over every signing. I think you’re right with TLR influencing things, so Hahn probably says, let’s go get A, B, C, but JR looks at TLR who says, no no, Leury and relievers, that’s all we need. So JR says to Hahn, get me Leury on at least 3 years and all the relievers.

But of course if this were 100%, then I think when this season ends at .500 or thereabouts, Hahn has to be looking for a new job, either by choice because he no longer wants to be handcuffed or because JR/TLR deny this and hang Hahn with another mediocre season as solely his fault.


If ifs and buts were candy and nuts, we’d all have a real good Christmas….


To me, there is one huge blunder- that is not signing Harper. He checked every box they needed (LH, power, high OBP, RF) and would have only cost $23M per year. I would bet that over the 13 years of his contract, the Sox will waste $23M each year on bad or unnecessary contracts. A lineup of Timmy, Yoan, Harper, Robert, Vaughn, Eloy, Abreu, Grandal (or another catcher if they didn’t sign Grandal) and anyone at 2nd would be devastating


I largely agree, though I would say that even more problematic was the decision not to sign Springer.

Look, if Harper was too expensive and it was a year too early, Springer solved both of those problems. To me that was the most obvious opportunity to add an all-star quality player to supplement the cost controlled core.

Last edited 6 months ago by soxygen