Role reversal: Sox built to avoid Cubs' troubles

What’s happening on the North Side should be a cautionary tale for the South Siders as roles reverse in Chicago baseball.

Four years ago, the Cubs were World Series champions, laying out a seemingly perfect rebuilding road map that ended in a ring and seemed to set up a few more. Their core of position players was young, exciting — and not going anywhere.

That same year, the White Sox started their rebuild by shipping Chris Sale and Adam Eaton out of town. A few months later, they sent José Quintana to the Cubs, who were making another run at the World Series at the other end of the Red Line.

Four years later, the two teams are, collectively, in a similar place: one contending and one starting over. But this time it’s the White Sox preparing for a World Series run and the Cubs dealing one of baseball’s best arms for a stack of lottery tickets.

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Some White Sox fans have turned their attention toward the opposite end of the Yu Darvish deal, to the San Diego Padres, who traded for two elite arms in two days. It doesn’t help that these are the same Padres to whom the White Sox sent Fernando Tatís Jr. and lost the Manny Machado sweepstakes.

As exciting a group as the Padres are putting together in San Diego, though, the Cubs’ end of this trade is perhaps more relevant to the White Sox. Proximity aside, the Cubs seem to be providing yet another road map for teams on the rise: a lesson in how it can all go wrong.

Not long ago, the Cubs were the model for all rebuilding teams, along with the Houston Astros. But while the Astros have reached the ALCS or the World Series in each of the last four seasons, the Cubs stalled out in the quest for perennial contention, reaching the NLCS in 2017 but only playing in three playoff games since, losing all three.

The North Side rebuild was undoubtedly successful, bringing an end to a 108-year championship drought. But suddenly, the Cubs are going back to the drawing board.

Whether in light of the Cubs' situation or what's befallen the Kansas City Royals, who won it all in 2015 before falling back to the bottom of the standings: Does only one World Series win make a grueling multi-year rebuilding project worth it?

Yes. A championship is baseball's ultimate accomplishment.

But winning brings adjusted expectations.

These rebuilt White Sox haven’t won anything yet, 2020’s brief stay in the postseason their first playoff appearance since 2008. Though plenty of fan bases have gone much longer than 15 years without their own title to celebrate, there’s no doubt that winning a World Series would be cause for South Sided euphoria and vindication for a years-long rebuilding project.

But Hahn often talks about long-term success. He might earn some snickers when he says “championships” and “parades” in plural. But that’s what he’s supposed to be doing, constructing as many championship-caliber teams as possible. And he’s done something that the Cubs, Royals and even Astros didn’t do, perhaps unlocking a key to making the South Side rebuild the new template.

If the Cubs’ predicament — in addition to trading Darvish, they non-tendered Kyle Schwarber, Kris Bryant’s name is perpetually in trade rumors, both Javy Báez and Anthony Rizzo are in the final year before free agency, and they have the same amount of homegrown pitching as they long have, which is none — has taught anything, it’s that keeping a contention window open is not easy.

Hahn’s made it easier, however, by locking up core pieces. Tim Anderson started the trend, and Eloy Jiménez, Luis Robert and Yoán Moncada have followed. Yasmani Grandal, Dallas Keuchel and José Abreu got multi-year contracts last winter. Some young players are still young enough to be factored into years’ worth of plans, guys like Nick Madrigal, Michael Kopech, Dylan Cease and the yet-to-arrive Andrew Vaughn. Even staff ace Lucas Giolito, who fans pray becomes the next to receive a long-term contract, is under control for three more seasons without one.

The Cubs seemed to have a good thing, too, of course, with five more years of Bryant, Báez, Rizzo and Schwarber following their World Series win. Obviously, numbers on a screen, like offseason trades, do not equal October glory. But with those long-term deals, Hahn has positioned the White Sox up for contention throughout much of the coming decade. The White Sox, too, have touted their financial flexibility the past few years, something the Cubs haven't had, showing the bind they were in by dumping Darvish's salary.

Will it all be enough to avoid replicating the Cubs’ tumble down the side of baseball’s mountain? Heck, will it all be enough to get to the top of said mountain in the first place?

In 2016 and for much of the four years since, as much as rivalry-steeped White Sox fans won’t want to admit it, the goal was to be like the Cubs.

That's still the case in one big way, winning the World Series.

But now the goal, too, is to do something they couldn't: last.