Synecdoche, New York Is a Place in Chicago

We’re currently hard at work on the 2025 Baseball Prospectus Annual, which will head to the presses in early January and should hit shelves not long after. For those not familiar, the Annual previews all of baseball, analyzing nearly 2,000 players, the game’s top 101 prospects, and provides a unique essay for every team.

What follows is last year’s essay for the Chicago White Sox, written by Sox Machine beat writer and BP alumnus James Fegan. It was published before the true horrors of the 2024 season came to light, but you’ll find that it had an inkling of what was to come.

If you missed Charlie Kaufman’s 2008 film Synecdoche, New York, you missed 124 minutes of runtime that contained at least as many, if not more genuinely upbeat moments than the 101-loss 2023 White Sox, and with a comparable body count to boot.

As much as the film’s larger themes—loss, regret, and a project of enormous personal hubris contorting into a living mausoleum for a series of naïve ambitions—align to the narrative arc of this embattled ballclub, a particular metaphor stabs directly at its heart. In the early portions of the film, a woman named Hazel purchases a home that is actively ablaze. While touring the home through the rising smoke, she airs concerns that the roaring fire will someday kill her. The realtor does not dismiss this for a second. It’s worth noting that the mounting burn damage does make for a more affordable acquisition price.

Near the end of the film, Hazel indeed dies of smoke inhalation by way of—get this—living in the burning house. Sometimes the exchange for upfront cost savings is an existentially larger bill coming due in the end.

In Synecdoche, somehow this inevitable and clearly telegraphed fate still provides a sense of shock and tragedy when it finally arrives. Maybe it’s because Hollywood largely likes to pretend smoke inhalation doesn’t exist, and has people running the equivalent of first-to-third through walls of flame all the time. But we see this person living and operating beside the inferno as a daily act. They have their standard supply of triumphs, disappointments, rising and falling actions, and the flames that will someday consume them become mere background scenery. She gets married, for Pete’s sake, and has kids! Kids who live in the burning house!

Just a ridiculous movie that I paid money to see multiple times. Separately, I was once a White Sox partial season-ticket holder.

Despite it all, Hazel has some late-in-the-game moments that make it feel possible she can achieve some measure of happiness, and that being constantly surrounded by the fire that will surely kill her might just be the idiosyncratic trappings to her underdog love story. Which is to say that within the past seven years, the White Sox have both possessed the consensus top farm system in the sport, had a player earn the MVP trophy, employed a nationally renowned broadcaster, held a lead in a decisive playoff game, and won 93 games in a season, despite being very much the Chicago White Sox the entire time.

“It’s a big decision, how one prefers to die,” the realtor offers during the showing. Every top baseball executive surely anticipates that their tenure is likely to end with them being blamed for every shortcoming, taking bullets for others and never openly acknowledging the constraints placed upon them by ownership, and yet they decide to forge ahead anyway. But perhaps former GM Rick Hahn still took a moment to be surprised that his long-awaited tenure, one he hoped to define by a decisive swing for an all-encompassing rebuild, would instead be most remembered for his boss shockingly hiring Tony La Russa at the moment of his plan’s realization. And it ended by his being fired alongside Ken Williams, as if they were a package deal without distinct ideas.

But for the last several years, the White Sox have been that burning house, where succumbing to its flames was a possibility—nay, inevitability—at all times. Their failings in foundational elements of organizational structure have mostly been fodder for caustic, privately told jokes by industry veterans. But when they bubbled up into publicly acknowledged issues and the odor of smoke became impossible to ignore, they have been responded to in a manner of someone who sees their ceiling cave in and begins Googling DIY construction tips as embers fill their living room, rather than evacuating…or you know, extinguishing the fire in some dedicated manner.

The post-2016 rebuild that once prompted the Sox to envision multiple championships was notable because no team had ever touted such a bounty of controllable major league assets while simultaneously being utterly hopeless going forward. They wound up losing 284 games in three years, but cashing out all their trade chips for highly ranked prospects was just the path of least resistance compared to examining how they arrived at such a predicament. Even their multi-year efforts have had the hallmarks and rapidly diminishing returns of a quick fix.

In kind, it’s ironic that Chris Getz has been promoted to general manager and tasked with a quick turnaround amid the wreckage of the 2023 season. Because ahead of 2017, Getz was brought in to initiate a gradual modernization of a troubled Sox player development system that already had arguably the most important crop of prospects in franchise history moving through it, breathing in all that smoke.

Ahead of the press conference introducing Getz as GM last September, longtime Sox chairman Jerry Reinsdorf stated his confidence that a team that has been blackening into ash for the last two and a half seasons could quickly return to contention. Concrete details were not given. He rooted some of that faith in what he feels is a greatly improved quality of players coming into the organization since Mike Shirley took over the scouting director job from Nick Hostetler after the 2019 draft.

Set aside briefly whether it was necessary to take a potshot at a still-present Sox employee, or whether Jake Burger’s post-trade deadline flourish with the Miami Marlins represents the Sox not getting as much return as other teams would have from Hostetler’s drafts. Following the logic of the comment, the Sox made a vitally needed change at scouting director, right after they had picked fourth overall in 2018, and third in 2019—the highest picks they would receive as part of their intentional tanking and rebuilding cycle.

All our eulogies could wind up a retelling of how we fishtailed down the road of life, over-correcting in response to all our mistakes well after the opportunity to meaningfully address them had passed. In Chicago’s case that oversteer was Lance Lynn, the big trade for a playoff-caliber starting pitcher that an up-and-coming Sox team needed. That is, needed earlier: He arrived right after a dormant 2020 trade deadline, a playoff series loss defined by his absence and manager Rick Renteria getting axed as he struggled to navigate through the pitching shortfall. That trade return Dane Dunning matured into an effective back-end starter for a World Series winning Rangers team, while Lynn’s late-career prime, contract extension, and the White Sox relevance all ended simultaneously, is somehow just a footnote.

The protagonist’s estranged younger daughter, Olive, is sort of the MacGuffin of Synecdoche; something for the hero to spend a lifetime hopelessly longing for against all reason. For the White Sox that’s been a healthy and productive season from Eloy Jiménez. But just as a late in life reunion between father and daughter is a weird and unsatisfying weak scene in the film, almost anti-comedy in its broadness, the Sox nearly coaxed a career-high in games played from Jiménez this past year by finally resigning him to DH (mostly). A convoluted upper leadership structure made it such that it was hard to find consensus on decisive action until after flames had charred a vital wing of the house beyond recognition. So Jiménez’s shift was just in time for the toll of countless injuries and resulting arrested development to sap power and lift from his bat, while the roster still teemed with poor defenders who are DH candidates themselves.

And sure, it’s typical for how the timing of the trade deadline and end of season management changes line up. But the White Sox fired Williams and Hahn three weeks after the duo teamed up to deal seven players at the end of July, in a desperate effort to restock an organization that had grown catastrophically bereft of both pitching and catching talent at their upper levels.

These are probably not the most telling examples of the White Sox kind of just operating peacefully alongside their own mounting destruction over the last several years. Driving Jason Benetti out of town and downgrading the television broadcast in the middle of a period where the on-field product isn’t worthwhile on its own doesn’t really fit with this trend, but is rather just an independently embarrassing thing. But as the brain is deprived of crucial oxygen and your lungs filled with pollutants, the memories and moments that flood the consciousness are more random than expository.

The “people ruining themselves through the obvious results of their own actions” genre has been popular for a few dozen centuries. But even while admiring its construction in so many ways, I cannot in good conscience recommend Synecdoche to anyone. Not after I tried to get my wife to watch it and she, a literal mental health therapist, demanded it shut off barely a third of the way in because it was “too depressing.”

But should you indulge your curiosity, at least try to get to the part where Phillip Seymour Hoffman’s character wins a prestigious and lucrative MacArthur “genius” grant right in time for his family life and physical health to start completely breaking down in response. The last two White Sox teams, predictably waylaid by injuries with little fallback plan and more encumbered by infighting at multiple levels as their dreams diminished, were by far the most expensive rosters in franchise history. When Hoffman’s character is richer than he’s ever been in his life but can’t get his leg to stop spasming, it very well could have been a scene from a Sox training room.

Ask any White Sox employee and they would probably say the worst thing about the 2023 season was losing all those games, everyone being miserable about it and a bunch of their friends getting fired. Maybe a fan would note the psychic whiplash of seeing two of their 2022 All-Stars having their team options declined to save money at the end of 2023. You can certainly see where they’re coming from with that. But for my money, there was a striking level of insult in the White Sox being largely unable to crack any of those “most disappointing teams” lists. It’s not that the pundits thought the team would be incredible; it’s that the failure was so deep as to feel predestined.

Sure, the Mets built the most expensive team ever and wound up selling at the deadline. And no one ever expects a Cardinals team to look like less than the sum of their parts. But the Yankees and Red Sox are both at threat level midnight for having what would constitute typical White Sox seasons. The Padres, long the White Sox’ Sisyphean twins on the left coast, posted a winning record and have had to call into question everything about themselves.

The White Sox have not been favorites for a time now, but this time last year were largely viewed as having the talent to win a barren AL Central—in the unlikely event that they got out of their own way. That it not only turned into 101 losses and the sixth-worst season in a not particularly strong franchise history, but also set off a wave of public recriminations and triggered a front office bloodletting and roster overhaul, and only the juiciest bits inspired even morbid curiosity from the baseball world is…just not the most flattering development.

Recall your most life-altering and personally crushing failure, and now imagine if all your peers reacted like they kind of saw it coming from a good ways off, shrugging helplessly, because the smoke was visible for miles.