Saturday Stew: Crosstown October?

It's only June, but the White Sox and Cubs are playing to the likes of a potential Crosstown Classic in October.

Friday marked the fifth anniversary of the White Sox trading then 17-year-old prospect Fernando Tatis, Jr. to the San Diego Padres and right-hander Erik Johnson in exchange for a veteran right-handed pitcher, James Shields.

At that point, the White Sox were in contention and hoping that Shields’ veteran presence would solidify their October hopes.

The crosstown rivals to the north were also in contention, and some were hoping for a potential all-Chicago World Series that October. Rick Morrissey wrote in a May 9, 2016 column for the Chicago Sun-Times:

“No championship is won in April and May, but it can be lost there. So talk about it while you can. Both teams have the staying power to make this a season-long conversation. Both have great pitching staffs.

Yes, we are getting ahead of ourselves. That’s the whole idea of sports. To dream big?”

At that time, a month before the Tatis for Shields swap, the White Sox were 22-10 and second to only the 24-6 Cubs when it came to the best record in baseball.

The Cubs would continue on their path to a World Series Championship by winning the National League Central by winning 103 games and toppling the Cleveland Indians in the Fall Classic to snap their 108-year championship drought.

The White Sox would stumble to a 78-84 record after the James Shields trade blew up in their faces, and the clubhouse was lost by former skipper Robin Ventura, who would be fired at the end of the season. Ventura was fired, and then veterans Chris Sale and Adam Eaton were traded to Boston and Washington respectively in trades that brought Lucas Giolito and Yoán Moncada to town while signaling the beginning of a full-on rebuilding effort.

As of Friday morning, the fifth anniversary of the Shields trade, the White Sox were 34-22 and sat atop the American League Central. The Cubs were 32-34 and sat atop the National League Central, currently considered the hottest baseball team.

Both teams have experienced different paths to this point from the last time some dreamed of a Crosstown World Series. The White Sox went into a full rebuild, lost 309 games, and are on their third manager since that date. The Cubs won it all in 2016, won 305 games since then, and have made three more trips to the postseason.

As it stands today, the two clubs are in inverse situations since the last time this conversation held any merit. The White Sox have the young core of superstars that look to be poised to contend for seasons to come. The Cubs, they’ve seen their window of contention come and potentially go, as they face a much more curious future beyond the 2021 campaign than their Southside counterparts.

Some would argue that this is the last shot at another World Series run with the current core on the Northside of town for the Cubs, while things are just getting started for the White Sox.

Yoán Moncada is re-emerging as one of the best third basemen in baseball after a COVID-19 2020 season that saw him struggle. Lucas Giolito is the undoubted staff ace of baseball's best rotation, and Jose Abreu is the reigning AL MVP. Then there’s Tim Anderson — with a batting title to boot — along with budding superstars Eloy Jiménez, Luis Robert, and more.

The White Sox are poised to be at the big boy table for the foreseeable future.

Kris Bryant and Javier Baez have reminded Cubs fans of their prowess at the dish on the other side of town, but both are set to be free agents at the season’s conclusion. Anthony Rizzo is set to be a free agent after this season, and Willson Contreras has only one year of control remaining beyond 2021.

The argument can be made that it’s now or never for the Cubs and the core group that won them a World Series title in 2016.

Both teams have potential pitfalls on their roster that could change the conversation as the summer draws on. The Cubs lack starting pitching depth, and most of their roster is currently performing to their career-bests, something that might not be very sustainable over the course of a marathon season that is the 162-game grind and postseason in Major League Baseball.

The White Sox rely on staunch starting pitching and depth in the absence of two prolific hitters in Eloy Jiménez and Luis Robert; both lost for much — if not all — of the 2021 season. The magic of Jake Lamb and Billy Hamilton might not be there for the duration of this season. What happens if the injury bug bites the White Sox again? Can they withstand another major injury blow this season?

In a year where our society is undoubtedly more divided than it’s been in many of our lives, a city divided by its dueling baseball teams might be just what the doctor ordered to bring us all together during these unprecedented times.

Sure, it’s still early June, and much may change this summer, but it’s nice to dream of a potential crosstown clash in the Fall Classic. Like Rick Morrissey said in his 2016 story for the Sun-Times, isn’t the point of sports to dream big?

Why not dream big, right?