The White Sox Are Getting a Facelift. They Need a New Head.

The White Sox are going to miss the playoffs in the AL Central, which is the baseball equivalent of failing driver’s ed. It’s disappointing but not particularly surprising; since winning the World Series in 2005, the Sox have made the postseason just three times and won a grand total of three games across all of those trips.

Shockingly, the White Sox have enjoyed remarkable front office continuity over that time. For most of the 21st century, the duo of Kenny Williams and Rick Hahn, in some combination of titles, was running the show. I say “was” because, as you well know, Williams and Hahn were fired on Tuesday.

There’s no structural reason the White Sox can’t be successful. They have history and branding half the league would kill for. They play in the third-largest media market in the U.S., and though they share it with a richer and more popular neighbor, if Houston and Philadelphia and Toronto can spend enough to put out a winning team, so can the White Sox. Most important, they play in the easiest division in baseball, where the last-place club in the AL East would have a decent shot at winning the division.

They’re also lucky enough to have an owner, Jerry Reinsdorf, who cares whether the team wins. Not every team can say the same. Unfortunately, Reinsdorf seems to care how the White Sox win.

No figure in modern society is so much like a feudal lord as an MLB owner. They answer to no one, except the commissioner, who serves at their collective whim and can be dismissed if he attempts to contravene their orders. The government doesn’t much care to regulate these teams; instead, they use their position as civic institutions to extract taxpayer money for real estate improvements. Sometimes that generosity is rewarded with a championship, sometimes not. What the hell are you going to do about it anyway?

Many owners are content to sit back and let their functionaries work. They understand that if the team wins, the owner will be popular even if the GM or team president actually made all the decisions. Some of them, I dare to hope, even understand the limits of their own expertise.

Not Reinsdorf, who has owned the White Sox for 42 years and the NBA’s Bulls for 38. No one knows the shine of reflected athletic glory better than Reinsdorf, who had the good fortune to purchase a team with an embryonic Michael Jordan on its books. But those successes have faded over the past decade and a half, as chronicled by Steven Goldman in Baseball Prospectus on Thursday. I won’t rehash much of that history here, because Steven gets it basically right: It won’t matter who the White Sox put in charge as long as that person has to answer to Reinsdorf.

Here’s the challenge for whoever runs the White Sox next — most likely incumbent assistant GM Chris Getz, who is the heavy favorite to sit in the big chair. The White Sox are a mid-payroll team. Their player acquisition has been occasionally excellent but generally inconsistent. Their player development has been much the same for pitchers, but sorely lacking for hitters. They have a franchise center fielder in Luis Robert Jr., a recent Cy Young finalist in Dylan Cease, who’s having a down year, and a few decent complementary players.

It’s not the easiest GM job in baseball, but it’s doable. There are absolutely executive candidates who could step into this job, reform the team’s scouting and development structures, and build a winning team around Robert on a budget in the next couple years. Many of those people are also charismatic and savvy enough to manage up to a difficult and interventionist owner. I’d argue that Williams, who was just 36 when Reinsdorf put him in charge in 2000, fit that bill at the time.

Unfortunately, Reinsdorf’s tastes have ossified; the current vintage would never countenance bringing in the only kind of outsider who could fix his problems. He has either struggled or refused to court outside help. When Williams was moved upstairs to executive vice president in 2012, Reinsdorf promoted Hahn from within. After the singular and combative Ozzie Guillen had run his course as manager, the White Sox wasted five forgettable seasons on the inexperienced and somnambulant Robin Ventura. When Ventura’s replacement, Rick Renteria, led the White Sox to the playoffs in 2020 — the team’s best season in over a decade — Reinsdorf responded by canning him and bringing back Tony La Russa.

La Russa had managed the White Sox briefly in the 1980s before embarking on a Hall of Fame career with the A’s and Cardinals that included six pennants and three World Series. But after he left the dugout in 2011, it was clear the game was passing him by. In the decade between managerial gigs, he had a pitiable run as chief baseball officer of the Diamondbacks. He replicated Renteria’s success in his first season, then went moldy and got fired before the end of the ensuing season. A year later, Reinsdorf is bringing La Russa back as a consultant.

When Reinsdorf does go outside the organization, it’s to Kansas City, from whence he pulled current manager Pedro Grifol. Former Royals GM Dayton Moore is also rumored to be joining the remade White Sox front office. As for Getz, he’s a former White Sox and Royals player who worked in Moore’s Kansas City front office.

It’s an inherently self-defeating and insular structure, one that’s reportedly allowed a rotten internal culture to fester. Hahn has been eating his now-infamous “ask me after the parade” quote for the past two seasons. This is a team that refused to spend $30 million a year on Bryce Harper or Manny Machado, but had no problem spreading the same amount of money around across three relief pitchers.

This is a house on a nice plot of land in a good neighborhood that is showing its age; it needs a new roof and major repairs. But because it’s owned by a man in denial who won’t brook disagreement, it’s getting a new kitchen backsplash instead of the major overhaul it needs.

Consider all this in the context of Reinsdorf’s other foray into the headlines: This grandee of Chicago sports is considering moving the team once its lease at Guaranteed Rate Field is up in six years. This is the final move of the feudal owner, the demand for tribute in exchange for the continued prestige of hosting a major league sports team.

The demand could not be more oddly timed. Maybe Reinsdorf will get his suitcase of cash, maybe not. But I struggle to think of anything he’s done to deserve it. The White Sox have been heading in the wrong direction for years now, and in changing out the front office, all Reinsdorf is doing is employing a new group of people to hide the maps from him.

Local and state government shouldn’t send Reinsdorf a dime. Instead, they should hire someone to whisper in his ear, like an old Habsburg, and tell him the check is in the mail. What works for the team ought to work for the public.