In the 120 years that Chicago has had two baseball teams, both have made it to the same postseason three times. The first time, they faced each other in the 1906 World Series. The White Sox, then a five-year-old franchise, beat the Cubs.
The next time both teams made it to October, in 2008, the divisional rounds were disasters: The Cubs got swept by the Dodgers, while the White Sox managed one win against the Rays.
Now, the Cubs and Sox are back playing fall baseball, at a time when both teams' trajectories appear headed in opposite directions. They could very well meet again in the World Series, but while the Cubs' window of contention is closing, the White Sox' is just opening.
The Cubs upended their reputation as baseball’s lovable losers with a trip to the NLCS in 2015, and quashed it for good by winning the World Series the following year. But the cadre of players responsible for that win is now set to scatter in the next two seasons. Kris Bryant and Javier Baez are at the end of arbitration in 2021, and could become unrestricted free agents after that. Jon Lester has a vesting option for next season, but may have made his final regular season start as a Cub over the weekend. The Cubs will likely pick up Anthony Rizzo’s option next year, but that could be it for him on the North Side.
But first-year manager David Ross — catcher for 2016's Series-winnnig squad — doesn't think they're done.
“What this group has done is really taken the narrative of this organization and turned it upside down,” Ross said before Saturday's loss to the White Sox, who the Cubs took 2 to 1 in the final series of the regular season. “I don’t think the end of the script is written yet for this group.”
While the Cubs were busy writing that script, the White Sox were engaging in a full-scale rebuild, beginning with the 2016 trades that sent Chris Sale to Boston and yielded Yoan Moncada, Michael Kopech, and Lucas Giolito. In the years since, vice president and GM Rick Hahn has built their farm system into one of the best in baseball, and Sox fans are finally seeing the payoff. With the emergence of future stars like Luis Robert and Nick Madrigal, the White Sox are looking a lot like the Cubs did six years ago.
This year, with the playoff format expanded due to COVID-19, the Cubs and White Sox start with a best-of-three wild-card series; the Sox go to Oakland starting Tuesday and the Cubs host the Marlins on Wednesday. If they win, they'll advance to a site-neutral divisional series. A lot has changed with both clubs since 2008, but like back then, the Cubs can still struggle to score. Twelve years ago, they fell to the Dodgers because they scored six runs to LA’s twenty.
The White Sox are a bigger question mark. They were the hottest team in baseball until a seven-game skid in the season’s final week and a half. Will that cold stretch linger in the postseason?
“I truly wish I had a magic pill to give it all that it needs,” manager Rick Renteria said before his team played Saturday.
If there were such a thing for the White Sox, it would be Jose Abreu. He's been the catalyst for countless wins this season, and on Saturday hit a bases-clearing double to end his team's losing streak. Currently, he has the fifth-highest OPS in the American League at .987.
If both the Cubs and White Sox made it to the World Series, a sad irony would hang over the matchup: In a series that guaranteed one half of town a home victory, the games would be played in Arlington, Texas, as a part of the MLB’s playoff bubble.
Still, a city series would generate palpable excitement, and the Cubs and Sox would match up well. The Cubs have the postseason experience, but the White Sox have gone undefeated against left-handed starting pitchers this season; in a seven-game series, the Cubs would likely have to rely on starts from lefties Lester and Jose Quintana. In their six games against each other during the regular season, each club won three. Both teams face challenging roads to Texas in late October, but it’s a possibility.
“Now you’ve got two teams that are doing it, and that's a lot of positives for the city,” Lester said following Saturday's matchup against the Sox. “Who knows what the playoffs will bring? And maybe we’ll meet again.”