The Chicago Cubs and Chicago White Sox are almost never playoff teams at the same time.
That makes for quite the fascinating free agent fodder, though. Instead of one of the teams pursuing players like a contender while the other does it as a rebuilder, they're now both going to be looking to bring ready-made contributors to the Windy City.
They still won't shop in all the same stores, but there's going to be more Chicago overlap on the free agent market than there has been in a while.
That could bear itself out most readily in a new free agent assessment of Cleveland Guardians left-handed pitcher Foster Griffin.
The Athletic's Jim Bowden recently ranked Griffin as his No. 14 free agent in MLB this offseason.
And notably for this discussion, he listed the Cubs and White Sox as two of the three "best fits" for Griffin this offseason — Bowden also listed the Pittsburgh Pirates .
Griffin is a fascinating pitcher who left MLB for Japan, built his ability up, then returned for 2026 with the Washington Nationals before being traded to Cleveland at the deadline.
The southpaw wasn't as good for the Guardians, but he was good in the playoffs, which should leave a positive energy in the eyes of those pursuing him.
Cleveland could try to bring Griffin back, too, unless his price gets too steep.
"Griffin was one of the most undervalued free-agent signings last offseason when he inked a one-year, $5.5 million deal with Washington after spending time pitching in Japan," Bowden writes. "He rewarded the Nationals by going 12-3 with a 3.06 ERA in 22 starts. When they couldn't extend him at the trade deadline, they dealt him to the Cleveland Guardians. He wasn't as successful with Cleveland, posting a 5.19 ERA, but his FIP was 3.54 and he pitched well for the Guardians in the postseason."
Griffin isn't a hard thrower, but that should mean he can fit into the middle of any rotation — he should transition gracefully from season to season without age or wear on his arm being a huge concern.
Bowden lists a pretty hefty projection for Griffin: three years and $67 million. That works out to $22.33 million per year.
"Griffin was technically a rookie this season, though he made his major-league debut in 2020 and pitched three full seasons in Japan as a starter," Bowden writes. "He is a durable left-handed starter who has solid command and a deep pitch mix. He should get plenty of multiyear offers this time in free agency."
The Nats got Griffin on a one-year deal for $5.5 million for 2026. If the Cubs or White Sox want him for 2027 and beyond, they'll have to pay up.
This article was originally published on HEAVY
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