For the last few years, it's been a one-sided argument. The Cubs won a World Series and made four straight playoff appearances before collapsing late in 2019. The White Sox opted for a rebuild and haven't made the postseason since 2008.
Things might be starting to turn though. The Cubs' late-season swoon showed that the roster isn't as strong as it once was and there are big decisions and challenges ahead regarding the long-term future of the team. The White Sox had a number of young players take positive steps in 2019 and the front office showed it is willing and capable of adding quality free agents to supplement the young core by landing Yasmani Grandal.
With all that in mind, MLB Network posed the question which team has a better roster for the next five years?
Ken Rosenthal and Jon Heyman both emphatically took the White Sox.
— MLB Network (@MLBNetwork) December 1, 2019
"Next five years, give me the White Sox roster," Rosenthal said. "Give me their farm system and I'd like to play with it because there's upside there that the Cubs don't have. In fact, the Cubs face a lot of questions in the coming years."
Rosenthal said that when adding in business potential, the Cubs' job might still be more enticing to a hypothetical baseball executive in this scenario. He also warned that Kris Bryant, Javy Baez, Kyle Schwarber and Anthony Rizzo are all free agents after 2021 and Willson Contreras a year later.
"It's kind of hit and miss whether you can keep these very big stars around for a long time and their contracts and their ability to keep them are mostly up in a year or two years," Heyman said.
"This is a team that's getting older," Rosenthal said of the Cubs. "It's a team that does not have a farm system at nearly the level of the White Sox, a team that has not produced young pitching in the Theo Epstein era. From that perspective, while the White Sox young pitching is not great, I like that team."
The White Sox have a crop of young position players on the team and more coming soon. It's easy to see the argument for why the White Sox roster is enticing going forward. It's eye-opening to hear they might be in a better position than the Cubs after all their recent success.
"The White Sox have an excellent roster and certainly if you include the minor league players," Heyman said. "Luis Robert is gonna be a major star. They got Kopech coming back. Giolito has obviously emerged. Moncada has improved. If you're just talking about the roster and the team, I'm going with the White Sox."
As if the two baseball writers didn't get White Sox fans excited enough, Rosenthal closed out with a closing thought with some juice to it.
"White Sox aren't done this offseason either," Rosenthal said. "They're going to get a starting pitcher, maybe two."