Aaron Nola Would Fit Perfectly In Chicago

Aaron Nola is still busy pitching in the playoffs, but when the Phillies season is over, he could be one of the most sought-after pitching free agents in the league.

Nola will be headed into his age-31 season in 2024, and he is at the end of a four-year, $45 million contract with Philadelphia. The Phillies exercised a $16 million club option for this season, but Nola is set to be an unrestricted free agent this winter.

He would fit perfectly in Chicago. On both sides of town.

The Cubs and White Sox will have rotation needs to fill during the offseason, and both teams should have the financial means to make Nola a competitive offer.

On the north side, the Cubs are coming off of a disappointing finish to a surprise 2023 season. They came just a game shy of getting a wild card spot and will be looking to compete more seriously next year. The top of the rotation is already strong, with Justin Steele as the de facto ace, but there are holes to fill. Marcus Stroman could take his player option for 2024 and stay in Chicago, but even if he does, Kyle Hendricks could be on his way out thanks to a vesting option for next year. If Stroman decides to pursue free agency this winter, the Cubs will have even deeper rotation needs.

In either case — especially the scenario where both Stroman and Hendricks are gone in 2024 — the Cubs will have to be aggressive for pitchers like Nola if they are going to want to compete for their division next season. They have emerging rotation options in Jordan Wicks and Javier Assad, but veteran presence is needed to provide the depth necessary for winning the NL Central.

The Cubs are projected to have a $170 million payroll in 2024, which leaves a lot of room below the first tier of the luxury tax threshold. But they also have decisions to make about guys like Cody Bellinger and other free agents, so targeting Nola may mean they spend less on other parts of the roster.

But if there’s a team with even greater rotation needs, it’s just a few miles south of Wrigley Field. As things currently stand, the White Sox 2024 rotation is Dylan Cease, Mike Clevinger, and maybe Touki Toussaint and Michael Kopech. Even in the best-case scenario with the current roster, they couldn’t fill out a five-man rotation. And that’s assuming they use their mutual option with Clevinger (he has said he’d like to stay with the Sox).

Clearly, the White Sox are going to have to be assertive in the winter market for free agent starters. They have a handful of pitching prospects in their top 30, but none with any major league experience yet, so looking to any of those pitchers to fill out the rotation next year is not wise.

That, and a team payroll that is projected to be over $100 million below the first tier of the luxury tax threshold, makes the south side of Chicago an appealing option. Nola’s likely desire to look for a long-term, top dollar contract could be an issue for the White Sox. Not that they couldn’t afford him, at least in theory, but their track record with doling out those kinds of contracts isn’t good. Andrew Benintendi at five years, $75 million is not only the largest contract they have on the books, but the largest they have issued in organization history.

But if they’re going to break from past precedent, Nola would be a good place to start. He’s exactly the kind of veteran workhorse the Sox need. He tossed almost 200 innings during the regular season and was worth just shy of four wins above replacement. Nola has pitched over 200 innings in a season three times in his career.

In this postseason thus far, he’s gone 3-0 with a 0.96 ERA. Nola is a big part of why the Phillies are two wins from their second consecutive World Series berth.

Both teams in Chicago have playoff dreams in the near future. The Cubs are much closer to making them a reality, and adding Nola would do a lot for that. Their rotation is already solid but lacks depth, and they could afford Nola — and even Bellinger — if they are willing to flirt with the competitive balance tax. The White Sox are realistically still a ways off from seriously competing for the postseason, but after back-to-back disappointing seasons, the new front office should show a beleaguered fanbase on the verge of dismay that their team is serious about winning again.

Both of Chicago’s teams have reasons to sign Nola as well as the financial picture needed to make him an enticing offer. Because of Nola’s resume, especially the one he’s building during this postseason, the Cubs and White Sox will have competition, no doubt. Regardless, there’s reason to keep an eye on Chicago when Nola’s free agency begins.