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It could be worse: A report from Chicago

Andrew Benintendi is playing better than Yankees left fielders, but that’s about the only thing going right on the South Side.

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MLB: Chicago White Sox at Toronto Blue Jays Nick Turchiaro-USA TODAY Sports

Hey, Yankees fans.

I know things are a little bit tough right now. They’re not horrible, especially after yesterday’s 12-run slumpbuster, but still, fourth place is fourth place. Giancarlo Stanton is hurt again, some of their best pitchers haven’t even been on a mound yet, Harrison Bader hasn’t seen the field either, and save for a few clutch Franchy Cordero long balls, none of his replacements have been able to hit a lick.

It’s not great, but it’s a good time to remind yourself that the Yankees have a strong foundation, built to withstand adversity in the long-run. As the resident AL Central-watcher here, I’m due to remind you that while the nail-biting nature of the AL East can be frustrating, it can always be worse. Just ask the Chicago White Sox.

“What happened to the White Sox?” many around the league seem to be asking as they’ve dropped seven consecutive games for a 7-18 start, their worst in nearly 40 seasons, just two years after back-to-back playoff appearances and the ascent of a young core that looked primed for more.

When Tim Anderson walked off Zack Britton into the cornfields in August 2021, the White Sox were five games ahead of a Yankees team in the midst of a bitter Wild Card chase with the rest of the AL East. About 20 months later, the Yankees are still in a brutal dogfight with three other teams chasing Tampa Bay’s coattails. Given expectations entering this season, the frustration is valid, but it sure beats what happened in Chicago.

MLB: New York Yankees at Chicago White Sox Jeffrey Becker-USA TODAY Sports

What happened isn’t very complicated. The hiring of Tony La Russa before the 2021 season destroyed the organic clubhouse culture that was developing among the team’s core; Jerry Reinsdorf refused to spend money at the top of the free agent market to address the clear holes that became evident after their 2021 ALDS loss to Houston; general manager Rick Hahn blew the money he was allowed to spend on bad relievers, bad humans, and Andrew Benintendi; and a series of other abuse scandals and lawsuits all combined to suck every ounce of life out of the franchise and bring fan relations to perhaps their lowest point ever.

With the Pirates’ extension of Bryan Reynolds now official, the White Sox will be in the company of only the Royals and A’s as the sole franchises yet to issue a nine-figure contract. Although they play in one of the biggest markets in the country, Reinsdorf refuses to act like it. Chicago did still set a franchise record deal this offseason — to Benintendi, who nonetheless seems to be justifying the Yankees’ decision to not match said deal with his torrid 1-WAR pace.

But not only do the White Sox generally refuse to spend money on good players in free agency, they also differ from the Yankees in generally refusing to take player development at all seriously. In spite of the frustration that comes with Yankees fandom, they’re almost certain to avoid a situation like Chicago’s because ultimately—despite what fans too close to judge impartially might think—they’re a serious organization that takes producing good baseball seriously. Why have the White Sox fallen off a cliff, fans around the league ask? Because they failed to meaningfully change anything about that part of their organization and essentially blew every draft of their rebuild phase.

MLB: New York Yankees at Tampa Bay Rays Nathan Ray Seebeck-USA TODAY Sports

Clubhouse leader José Abreu was forced off the roster as a consequence of using first- or second-round picks on Jake Burger, Gavin Sheets, and Andrew Vaughn between 2017-19, who have collectively produced fewer than one WAR in nearly 2000 trips to the plate. The sum of the value received from the No. 4 pick in the 2018 draft — one spot ahead of the resurgent Jarred Kelenic — was Nick Madrigal (1.6 WAR), who became Craig Kimbrel (0.0 WAR), who became AJ Pollock (0.4 WAR), who became a free agent.

Things are frustrating for the Yankees, but the reason they’re frustrating instead of disastrous is that they do a good job of maintaining a steady, if not always spectacular, pipeline of big-league caliber players (or prospects) from the end of the first round and beyond. The White Sox are falling apart because when injuries strike their star players (and they always do), their immediate depth is replacement level, and they don’t have the depth in their farm system to trade for anything better. The Frankie Montas and Scott Effross deals don’t look great for Brian Cashman, but the entire point of what they’ve built is that losing out on all that talent for essentially zero return is something that the organization can weather without blinking. Teams like the White Sox are forced to put all of their trade eggs in a few small baskets. They picked the wrong baskets.

Ultimately, it comes down to bad decision-making. There’s no reason that the White Sox couldn’t run a top-five payroll, and while they choose not to, GM Hahn was still given a nearly $200 million payroll to play with. The Yankees are frustrating instead of spiraling because for every bad deal that Cashman has made in recent years, he’s found a free agent success story that’s kept the team afloat at one point or another. The White Sox have no equivalent to DJ LeMahieu, Anthony Rizzo, or Nestor Cortes playing key roles to this day. Not only have the players they signed to similar mid-level contracts flamed out or failed to remain healthy — Dallas Keuchel and Yasmani Grandal combined for an incredible -2.8 bWAR last season — they simply haven’t even made any such signings beyond Benintendi.

Serious organizations go out and spend money on a Gerrit Cole or an Aaron Judge once in a while. Unserious organizations balk at the chance to close on Bryce Harper or Manny Machado at $25-$30 million per season and instead spread that money around to Joe Kelly, Kendall Graveman, and Mike Clevinger. It’s a genuinely disgusting allocation of resources.

Say what you want about Brian Cashman and the Yankees front office, but they’ve built an organization that’s a lot more difficult to fold than the one that Ken Williams and Rick Hahn have built in Chicago in roughly the same time period. Things aren’t going as planned in New York right now: injuries are everywhere, several spots in the lineup are black holes, and the rest of the AL East looks to be somehow even more competitive than anyone anticipated. But it’s also a good reminder that the foundation of the Yankees is strong. The White Sox are collapsing because their foundation is rotten, down to the very roots. The Yankees will make you want to pull your hair out. But at least they’ll always make you care.