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Chicago White Sox Continue on Road to Nowhere

The South Siders mortgaged their future for an opportunity to land a marquee free agent. Missing out on Manny Machado is a disaster for a team that has little to show for its tanking efforts.

Getty Images/Ringer illustration

So Manny Machado will wear brown. On Tuesday, the superstar free agent inked a 10-year, $300 million deal with the San Diego Padres.

You can make the case that this is a good thing—for Machado, for baseball, and for your own personal favorite team. (Allow my colleague Zach Kram to assist.) But for the Chicago White Sox, it’s—well, it’s hard to go too far. It’s a disaster. It’s an embarrassment. And, maybe worst of all, it’s an indictment of years of poor strategy.

For much of the winter, the White Sox appeared to be the most likely candidate to win the Machado sweepstakes. This was in part because of the tepid free-agency market—aside from the Phillies, who have made clear that their primary recruiting interest is the still-unattached Bryce Harper, few teams were rumored to be offering much in their pursuit of Machado. San Diego was a dark horse, to put it mildly. (The Yankees, we’ve since learned, met with Machado but didn’t so much as put an offer together.)

So it was the White Sox who seemed poised to do the thing. The team went to extreme lengths to reshape itself for Machado, in ways both traditional and less so. In December, the team traded for first baseman Yonder Alonso, Machado’s brother-in-law, and weeks later signed outfielder Jon Jay, a close friend of Machado’s. He, Alonso, and Jay train together in Miami each offseason; as spring training got underway in Glendale, Arizona, an empty locker just so happened to be placed immediately next to the ones belonging to Machado’s pals.

But it wasn’t just this offseason: The Sox had been working toward signing Machado, or at least someone of his caliber, for years. After winning the World Series in 2005—the franchise’s first championship in nearly 90 years—the Sox spent years mired in mediocrity and ill-advised, or at least ill-executed, attempts to win now, which mostly consisted of shipping off prospects in exchange for just-over-the-hill veterans. In June 2016, the Sox traded current no. 2 MLB prospect Fernando Tatis Jr. to (who else?) the Padres in exchange for just-about-to-fall-apart starting pitcher James Shields. Not long afterward, the team entered a committed tank, one that required, as these things do, some near-term pain: here, in the form of jettisoning ace Chris Sale to the Red Sox and outfielder Adam Eaton to the Nationals.

The goals of such a rebuild are twofold. One: Acquire prospects (the Sale and Eaton trades included returns of, among others, then-prospects Yoán Moncada and Lucas Giolito). Two: Clear out enough payroll space so that, as pieces begin to fall into place (lookin’ at you, Eloy Jimenez), a big star can be signed. The main thing, though, is to have a plan, and the White Sox seemingly did: Spend a few seasons saving and hoarding in the basement, pick up a superstar free agent along the way—maybe one who could fill the Sox’s perpetual hole at third base, a veteran who might be able to steer the newly acquired young guys—and presto changeo, contention.

They were doing it. 2017: 67–95 record and fourth in the AL Central. 2018: 62–100 record and fourth in the AL Central. They ranked 26th and then 29th in team payroll in those seasons. To pick up a superstar free agent, though, you have to pay accordingly, and that is where this story falls apart.

As news of Machado’s decision spread Tuesday—my personal favorite response: “I’ll bite, who are the Padres”—the sentiment coming from White Sox HQ was … surprise. “I’m wearing my shades so you can’t see the shock in my eyes,” said Kenny Williams, the team’s executive vice president. “We’ve had better days,” he told WGN-TV’s Dan Roan.

The White Sox under Jerry Reinsdorf, who bought the team in 1981, have long had a reputation for cheapness. The White Sox’s largest free-agent signing to date? It was $68 million over six years to first baseman José Abreu, back in 2013. The White Sox reportedly offered Machado $250 million over eight years, plus incentives—more per year than the Padres, but well below the market baseline set when the Nationals offered Harper $300 million and 10 years at the start of the offseason. (That offer, obviously, was declined, suggesting the market value for the pair could be still higher.) It’s not clear whether Machado’s decision came down to the total number of years on offer, but given reports that the Sox were being stubborn about it—well, it’s not hard to imagine a situation in which Chicago just refused to compete. Williams tried to justify the apparent stinginess thusly: “[W]e have to project putting together a winning roster, a total winning roster.” Where is the rest of that winning roster? When will it arrive? Can a winning roster happen with a team that refuses to pay top dollar for sorely needed talent?

Let’s be clear: For the White Sox, this isn’t an aw-shucks moment, or a case of getting one-upped by an offer that was impossible either to predict or to match, seeing as they were capable of both. The South Siders were never going to be a World Series contender in 2019, and that, up until the moment Machado signed with San Diego, was fine—a rebuild takes some time. Machado is not the last free agent of his caliber—and, indeed, Harper hasn’t officially been ruled out, even if the Sox haven’t particularly seemed like contenders. But the White Sox’s failure Tuesday speaks volumes. A tank is worth it only if there’s something on the other side, and in declining—through cheapness or incompetence or both—to compete for Machado, Reinsdorf and the White Sox have revealed that, as has so often been the case for this team, there might not be anything there at all.