Free agency always opens the door to a little nostalgia, and for the Cubs, this winter could bring a few familiar names back into the conversation. Former Chicago players are set to hit the market, and while reunions rarely come together cleanly, the Cubs do have roster needs that make a second look worth taking.
The most intriguing name in that group is Michael Soroka. Among the former Cubs available this offseason, he’s the one most likely to draw real interest.
Soroka found success with the Diamondbacks last year, but durability remains part of the conversation after he logged just 116 innings. If the Cubs make a bigger move or two to shore up the rotation before circling back, Soroka could still fit into the picture.
If not, he probably won’t be the headline addition.
Sean Newcomb is another former Cub who could make sense in the right role. Chicago may have moved on from him too soon after he struggled to a 9.13 ERA in 17 appearances with the club in 2022.
Since then, he’s rebuilt his value and emerged as one of the better left-handed relief pitchers in baseball, including a 3.09 ERA with the White Sox this year. With the Cubs needing more left-handed help in the bullpen, Newcomb could be a realistic target.
Joc Pederson brings a different kind of fit. The Cubs never really got the full Pederson experience in 2021, when his trade was one of the clearest signs the club was heading toward selling at that year’s deadline.
Since then, he’s settled into the mold of a classic DH, with power against right-handed pitching. If Ian Happ and Seiya Suzuki both end up leaving, there’s at least a case for Chicago to explore Pederson as a power bat.
Still, his lack of defensive value makes him easier to pass over.
Andrew Kittredge is the least convincing reunion of the bunch. If his club option in 2026 had been under $9 million, the Cubs might have thought harder about keeping him instead of sending him back to the Baltimore Orioles.
He did post a 3.54 ERA in 2026, but the deeper numbers point in the wrong direction. He struck out only 18.7% of the hitters he faced that year, and opponents hit .271 against him.
That’s not the kind of move the Cubs should be chasing this offseason.
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Josiah Hartshorn, Owen Ayers and Brooks Caple are the kind of prospects that make this conversation tricky, because all three have given the organization reasons to believe they can matter soon. The Cubs also have to protect their pitching depth with free agency looming, which only raises the stakes on every possible move. After some past trade mistakes, this is the kind of winter where restraint may be just as important as ambition. [Read more 🡒]
Cubs Could Finally Target The Bullpen Fix Fans Have Wanted
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One name that keeps surfacing as a fit is Adrian Morejon, a left-handed reliever whose recent work has put him on the radar as one of the more appealing free-agent options available. He looks like the kind of arm the Cubs have been missing, though landing him will not be simple, with other clubs expected to chase him too, including the Padres. [Read more 🡒]
Cubs Pitching Search Could Lead To A Former Astros Gamble
The Cubs are heading into the offseason with a clear pitching problem, and it is one that will shape much of their winter. With several arms departing in free agency, the front office has to find ways to add depth and upside without overcommitting, which is why even the more modest names on the market are worth a long look as Chicago tries to patch together a sturdier staff.
One of those possibilities is Ryan Weiss, a former Astros arm whose profile still carries some intrigue despite an uneven run in Houston. The appeal is obvious enough for a team in Chicagos position: he brings power stuff and enough raw traits to suggest there may be something to work with, even if the results have not matched the talent yet. For the Cubs, the question is whether a low-risk bet on a pitcher like Weiss can fit into a broader plan to rebuild the rotation without forcing the club into a bigger splash than it wants to make. [Read more 🡒]