How the rebuild stalled: A play in 10 acts

Despite trading premium talent for star prospects back in 2016-17, Chicago’s contention window is closing mighty quickly. After two playoff appearances (and two early playoff losses) in 2020 and 2021, the South Siders were one of baseball’s most disappointing teams in 2022. Incredibly, they are far worse in 2023.

How did we get here? Let’s pinpoint 10 significant moments that have led the team to this position.

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2018 season

After a respectable first season of the rebuild, the White Sox suffered a setback in 2018, when they went 62-100. Sure, the major league team’s record was not that important at that point, as nobody expected the White Sox to contend in 2018. However, there were some causes for concern, one of which was all of the injuries to young talent.

The biggest setback involved Michael Kopech, who needed Tommy John surgery after getting a small taste of major league action. As for players who started the year in the majors, infielders Tim Anderson and Yoán Moncada were nothing special. Reynaldo López had a 3.91 ERA but a 4.63 FIP. I’ll bet you remember how Lucas Giolito performed in 2018.

Although bottoming out gave the White Sox a higher draft pick, it also meant they had a longer way to go before competing for a playoff spot. The following offseason was a crucial one, but fortunately, they had an abundance of opportunities to make substantial improvements.

2018-19 offseason

Bryce Harper and Manny Machado were available, and White Sox fans were hyped. But, wait, why were they excited? Owner Jerry Reinsdorf does not beat the market for star players in free agency. Well, the market was mighty soft that offseason. Many free agents settled for team-friendly deals that winter.

As for Machado (the South Siders’ biggest target), incredibly, not many teams were seriously bidding on him. The White Sox appeared to be the frontrunners as of late January, and they had reportedly made a serious offer. However, after the contract was offered, updates were hard to come by, and I felt that Machado was underwhelmed (if it was a great offer, he probably would have accepted it by now, I thought).

Then the Padres, who were in a similar situation to the White Sox, swooped in. San Diego was also rebuilding, and had one of the strongest farm systems in baseball. They saw that nobody was impressing Machado, and took full advantage. This was not a situation where Machado took less money to play for a team that was already competing. It was also not a situation where one team beat the market by miles to the point where Machado’s services were not worth the insane cost. In other words, this was an inexcusable way to miss out on a future Hall of Fame talent. Then, after missing out on Machado, the White Sox did nothing else noteworthy.

Rick Hahn saying some fans rooted for the rebuild to fail after a losing streak in July 2019

The White Sox were surprisingly decent in the first half of 2019, entering the All-Star Game at 42-44. Giolito and Moncada had breakout seasons. Eloy Jiménez started flexing his power after a slow start to his MLB career. Then, the week after the Midsummer Classic, the bottom fell out. The White Sox lost seven in a row, and most of those games were blowouts.

With the White Sox finally firmly out of contention, negative vibes crept back in. Shortly after, Rick Hahn made an appearance at a fan event at Reggie’s, where he fielded questions.

In one answer, he mentioned that some critical fans would prefer to see the rebuild fail so that they could be “correct” in predicting failure instead of celebrating a World Series. Hahn also talked about how these fans are not open-minded about transactions, often having an instantaneous response of “This is horse [expletive]” without thinking it through.

I am still unsure why Hahn felt the need to say this. Many of the fans he was referring to have been closely following the team for years, and have seen the type of mistakes he has made. They paid attention during the failure of 2013-16 and hoped he did not make the same mistakes again.

As it turns out, those concerns were valid.

Two starting pitchers in 2020

In a bizarre all-around year due to Covid, the White Sox made the playoffs for the first time in 12 seasons. There were some exciting moments during the truncated, 60-game regular season, such as the South Siders’ explosive power at Wrigley Field and Giolito’s no-hitter against Pittsburgh.

Speaking of Giolito, though, he was one of only two reliable starting pitchers on the team.

The front office did not address the rotation, and the issue was compounded due to Ricky Rentería’s lack of experience with using openers. This came back to haunt the White Sox during the deciding game of their Wild Card series against Oakland.

Tony La Russa hiring

Typically, I am open-minded when it comes to managerial hires, and I am happy to give new managers a chance. However, this hiring had enough red flags to where it was an exception. La Russa had not managed since 2011, and there were serious questions about his ability to connect with his new team’s young core, especially considering that a few players did not follow traditional (unwritten) rules. On top of that, La Russa had been charged with his second DUI earlier that year. Jerry Reinsdorf had forced his hand on the organization, still feeling guilty about La Russa being let go 34 years earlier. It was a bad hire on paper, and it was a bad hire in practice.

Second half of 2021

After exploding out of the gate at 43-25 in 2021, the final 94 games were nothing special. With a substantial lead in a bad division, the White Sox were not tested often down the stretch. They went 50-44 after that great start, to cruise to a 93-69 finish. It was still a successful regular season, but they finished two games behind the mighty Astros, and as a result, Houston had home-field advantage for the ALDS. Throughout the second half, the White Sox faded from one the very best in baseball to roughly average among playoff teams. Could they return to their early season form as the level of difficulty ramped up?

ALDS vs. the Astros

Many White Sox fans see Leury García’s home run as the peak of the rebuild. It was a thrilling moment, and it propelled the White Sox to a Game 3 victory. I am grateful for that moment, but despite it, the Astros handily won the series. It was nearly all Houston outside of García’s big blast. The only silver lining is that the lopsided nature of the series likely meant that having home-field advantage would have made no difference in the outcome.

2022 season

With expectations higher than they had been since 2006, the White Sox were somehow significantly more disappointing than they were in 2006. The AL Central was weak again, but this time, the White Sox couldn’t coast, and were outclassed by the Guardians. Chicago simply would not venture more than a few games from .500. They needed help at the deadline, but they only got Jake Diekman. At least Hahn felt as disappointed as the fans.

Down the stretch, the Guardians finally caught fire and surged to the division title before being eliminated in the ALDS. During the Guardians’ celebration of their division title, a couple of players seemed to mock the White Sox by yelling “[expletive] the White Sox” and chanting “Fire Tony.” Normally, I would have been furious, but I was upset enough at the White Sox that I thought, good for them. We deserve it.

Hahn press conference

At the end of the 2022 season, Hahn made several comments that rightfully bothered the general community of White Sox fans. With the Guardians players and social media team dunking on the White Sox, the horse having run a mile from the barn, and the house on fire, Hahn defended himself by noting he won Executive of the Year two years earlier, and that six months ago, the White Sox were a popular pick to be in the World Series. His standards had dropped substantially since he implied that his work was not complete until there was a parade.

Hahn also said he believes he is more critical of his work than anyone else, and that if he ever felt that he was the wrong person for the job, he would step aside. That cannot be correct. There are people who are far more critical than I am of Hahn, yet I believe he is the wrong person of the job. Would he ever voluntarily step aside? Consider me doubtful.

This was the same press conference where La Russa’s retirement was officially announced. To his credit, La Russa took ownership of the team’s failures. At this moment, La Russa passed the torch to Hahn for person the fan base was most irritated at.

2022-23 offseason

That press conference kicked off another lackluster offseason. Sure, the White Sox made their biggest-ever commitment in terms of contract dollars with Andrew Benintendi’s five-year, $75 million deal. On paper, this was a small step in the right direction, as Benintendi seemed to at least partially fill a couple of glaring gaps on the roster. However, Benintendi was far from a crown jewel.

Elvis Andrus was an OK but unremarkable addition. Topping the market for [redacted] was a horrible idea. Unlike the 2018-19 offseason, when the White Sox actually had a decent chance of making a big splash, there was not even a whisper of the White Sox doing that. Ultimately, the White Sox needed reinforcements to get back on track after 2022, and they fell way short. That set up the team for the epic failure we have seen through the first quarter of the 2023 season.

On top of that, the team cancelled SoxFest, even though the Cubs had their convention within a week of when the White Sox would have had theirs. Why? “Several factors.” It is not too difficult to guess what those were.

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