A White Sox Fan’s Eulogy for the Worst Baseball Team of All Time

Here’s a humiliating admission: At the start of the 2024 MLB season, I wagered a decent amount of money on the Chicago White Sox to not only make the playoffs, but to win the American League pennant.

Granted, this wasn’t real money, per se. It wasn’t even a real wager, in the sense that I thought I might win anything. Noticing an absurdly generous introductory offer from a major online sports gambling company–cancer on American men that sports betting now unquestionably is–I placed a tiny $5 wager on a likely football winner and then collected $250 in free “bonus bets” for doing so, subsequently wagering that whole digital windfall on the Chicago White Sox to complete such Herculean tasks as “make the playoffs.”

Not because I thought that they likely would, but because it was so very likely that they would not, in terms of the bettor’s odds. If my lifelong baseball team was going to pick a year to go on an unexpected run … well hey, at least I would profit from it. Crazier things have happened, I told myself–every year there’s a team that is supposed to be terrible, but turns out to be halfway decent. Maybe there’s some small chance that the 100-loss White Sox of 2023 would have an abrupt turnaround and make me a big, long shot payday. They won the division as recently as 2021! It’s reasonable enough, right?

Now in October of 2024, the answer is just starting to come into focus: I may have been wrong.

As wrong as one could conceivably be in such a situation. As wrong as anyone has ever been about anything baseball-related, in the history of baseball. Just hilariously wrong, to the point of comic overkill. Not only were the 2024 Chicago White Sox not making the playoffs, they went on to finish with a record of 41-121, surpassing the losses total of the 1962 Mets to become, at least technically, the worst baseball team in the history of the “modern era” since 1900. This was badness extrapolated to the form of high art, in the vein of Tommy Wiseau’s The Room. The team shattered historic records for poor play on a seemingly weekly basis, including such feats as a 3-22 start of the season, or a 16-game home losing streak, or a 21-game overall losing streak that was the longest since the 1988 Orioles.

Suffice to say, I won’t be seeing that sports gambling payday courtesy of the 2024 Chicago White Sox.

There’s probably some White Sox fan out there who would find some shred of comfort in the idea that there have technically been even worse teams in baseball history than what we saw in the last six months. But you’ll forgive me if I can draw little solace from the fact that they theoretically weren’t worse than the 20-win (in 154 games) Cleveland Spiders of 1899. The games those two teams were playing would barely even be recognizable to either of them–comparing them would be about as relevant to today’s statistics as the relative merits of the guys chucking balls into James Naismith’s peach baskets when compared to the career of Lebron James. Regardless of precisely how bad, the 2024 White Sox were bad on an undeniably epic, historic scale. No fandom in recent memory has seen something quite on this level of embarrassment. Which begs the question: As a Sox fan, where does one even go from here? How do you summon up the enthusiasm to embark on another long, painful rebuild when this result you just witnessed was the ultimate fruit of the last long, painful rebuild?

Because lest we forget, the White Sox have just exited what was devised to be a “championship window” made possible by a stretch of concerted tanking from 2016-2019. That rebuild arguably began with the trade of incoming NL Cy Young Chris Sale to the Boston Red Sox in 2016, bringing back players such as Michael Kopech and Yoán Moncada, then the #1 prospect in baseball. They then traded Adam Eaton for a package that included Lucas Giolito, Dane Dunning and Reynaldo Lopez, and in 2017 traded pitcher José Quintana for a return built around Dylan Cease and Eloy Jiménez. At the same time, the Sox built what was envisioned as a fearsome lineup with the debut of Tim Anderson in 2016 and the international signing of Luis Robert Jr. in 2017, along with drafting Andrew Vaughn at #3 in 2019. It seemed like the offensive pieces in particular were there. The team was exciting, with the verve of Anderson in particular as its signature flourish, and by 2021 they captured the division title, winning 93 games.

But at the same time, the rebuilding White Sox continuously missed out on making the kind of big, signature moves that might have put the promising squad of young players over the top. They were heavily connected to franchise free agent players such as Bryce Harper, Manny Machado and Zack Wheeler in 2018-2019, and in each case ultimately failed to make a compelling enough case to sign them. After missing on Machado in 2019, GM Rick Hahn tried to soothe the fanbase, assuring them that “the money will be spent.”

The phrase would go on to become a lightning rod for criticism and a bitter refrain of the ChiSox faithful in the years to follow, as the rebuild began to falter in 2022 and imploded outright in 2023. By the beginning of this season, no White Sox fan honestly expected newly installed GM Chris Getz–another seeming pushover mouthpiece of owner Jerry Reinsdorf–to right the ship any time soon. But at the very least, they were hoping there might be a marginal improvement from the dregs of 2023’s 100-loss season, which Getz hoped to deliver with a greater focus on defense, pitching and fundamentals. Not even the most pessimistic Sox fan was calling for incompetence on a literally historic level, but that’s indeed what we received.

For a microcosm of how wrong this White Sox era could go, consider the case of one Andrew Benintendi, the 30-year-old veteran outfielder. In 2024, he managed to match his career high of 20 home runs … while simultaneously having the second worst overall season of his professional career, better only than the first year of his White Sox tenure after signing a 5-year, $75 million contract. Not many players with 9 years of service time could ever say that they’d matched their season high in home runs while simultaneously being 71 points beneath their career OPS, but Benintendi can, thanks to batting .229 on the year. Coupled with declining defensive metrics, he managed to match his career-best power production while contributing a whopping negative .8 wins above replacement for the team.

Oh, and that 5-year, $75 million contract? That’s the richest that the White Sox have ever handed out in team history, thanks to the penny pinching of Reinsdorf. The money will be spent? Really? How can any team even pretend to say that when they’re one of only two remaining (the other is the formerly Oakland A’s) that has never signed a $100 million contract?

There were countless other disparate disappointments of course, that led to the slamming shut of that so-called championship window. Tim Anderson was one of the blossoming stars of Major League Baseball as recently as 2022, and then fell off a cliff after injury but especially after revelations surrounding his personal life and marriage. Two years later, he’s out of baseball. Jose Abreu just fell off an age-related cliff. Andrew Vaughn hasn’t come close to living up to the offensive level expected of the #3 pick in the 2019 draft, and certainly not enough to offset his horrendous defense and base running, which has given him a barely positive WAR after four full seasons.

And then there’s the perpetually injured squad of Moncada, Jimenez and Robert, none of whom ever managed to succeed in driving each other in, given that two of the three were typically nursing lingering soft tissue injuries on the IL at any given time. Others like Michael Kopech or Reynaldo Lopez seemed to suddenly blossom with another team as soon as they got away from the White Sox, with Kopech claiming that he apparently needed the Dodgers’ organization to tell him not to throw his fastball 90 percent of the time. To which I say: Look, I know this organization sucks, but I’m pretty sure they’re not THAT oblivious that they didn’t tell you the same thing, Mike. Maybe it would be a bad idea for any pitcher to throw 90 percent fastballs?

All of these atrocities, I must admit I observed from a fairly reserved distance. I don’t live in the Chicago area these days, and although I still fairly regularly watched the games via MLB’s streaming service, very little of my own self-worth has been mixed up in White Sox fandom in recent years. As a fan of the larger game, my passion for baseball itself wasn’t truly threatened by seeing my own team–the one I rooted for as a kid–descend to historic lows. Believe it or not, there were even moments of hope and positivity for the future, when it came to watching the hapless 2024 White Sox, particularly in the form of a surprisingly decent core of starting pitching. The likes of an emergent Garrett Crochet, Drew Thorpe, Jairo Iriarte and Sean Burke could provide a solid enough foundation, while top prospects Noah Schultz and Hagen Smith are waiting in the wings to join them. These are the kinds of arms that successful Major League Baseball teams tend to be built around. But with that said … successful MLB teams also typically have a plan in place for how they might also score a few runs. And in that capacity, there genuinely seems to be no help coming for the Sox, who scored merely 507 runs in 2024–almost 100 less than the 29th place Tampa Bay Rays.

Now that is how you lose 121 games. Blowing an incredible 37 saves helped, of course.

What more can you say about a team that finished its year with only four more total wins than blown saves? White Sox fans will endure this blow with the same brand of humility they possessed before the team shook off its 88-year championship drought by winning the World Series in 2005. As it was then, the chip on fans’ shoulders will grow to titanic, iceberg-like proportions as they wait, jealously spying as the Cubs across town draw crowds whether or not they contend on any given year.

The Sox have been here before; they know how to take it on the chin. The second team of the Second City will lay in wait, as fans hope that owner Jerry Reinsdorf will one day pass the team to someone who demonstrates a genuine desire to do everything it takes to win. Maybe one day he’ll make good on his threats to move them to Nashville, or maybe (this seems rarer) he’ll break out the checkbook to sign a free agent of actual consequence. The team and the uniquely tough fandom will persevere, but they won’t forget. No one will forget 2024, much as they might like to. True infamy of this nature has to be earned, and this group managed to earn it. Let them wear it into 2025, and then initiate the messy act of beginning again. In this moment, we need to wallow in it.