The Chicago Cubs are heading into the offseason with a desperate need to focus on pitching and a relative little bit of time in which to do a lot.
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The team’s entire end-of-season starting rotation may end up leaving via free agency. Matthew Boyd is expected to walk away from his part of the 2027 $15 million mutual option he has with the Cubs for 2027. Clay Holmes is expected to turn down his $12 million player option and test his value in the free agent market. Shota Imanaga, Kevin Gausman, and David Peterson, meanwhile, are set to become unrestricted free agents at the end of the baseball season.
What remains for Chicago is a handful of pitchers dealing with injury and/or inconsistency—such as Justin Steele, Cade Horton, Ben Brown, and Edward Cabrera—whose 2027 is not guaranteed at all.
Jed Hoyer and the Cubs front office will have to be aggressive this winter/spring to bring in as many quality names as possible with the surplus budget they have from big money coming off the books.
Part of that aggression could come via trades with teams eager to ditch payroll burdens—like the Miami Marlins.
Revisiting a Sandy Alcantara trade?
Mar 27, 2025; Miami, Florida, USA; Miami Marlins starting pitcher Sandy Alcantara (22) looks on against the Pittsburgh Pirates during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images
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Specifically, it could be time to revisit the team’s interest in Sandy Alcantara.
The Cubs were tied extensively to Alcantara prior to the 2025 trade deadline, as the veteran righty was hitting full speed after recovering from 2023 Tommy John surgery. They were also tied to Alcantara early this past offseason, before the Cubs pulled the trigger on the trade for the Marlins’ Edward Cabrera instead.
Does it make sense?
Miami Marlins starting pitcher Sandy Alcantara (22) looks on against the Atlanta Braves during the second inning at Roger Dean Chevrolet Stadium. Mandatory Credit: Sam Navarro-Imagn Images
For 2027, though, a trade for Alcantara still makes sense.
For one, the price is right. Alcantara will be pitching in 2027 on a $21 million club option, which is a bargain in this market for a pitcher who can bring what the 31-year-old still can. He then will head off to free agency. In 2026, he led the majors with 214 innings pitched and 33 games started while posting a 3.87 ERA.
While he hasn’t been the dominant ace he was prior to the Tommy John surgery, his velocity is back to pre-surgery level, as is his overall stuff. As such, he’s definitely a candidate for an even bigger bounce back season in 2027.
Jordan Campbell of Cubbies Crib recently brought up the idea of the Cubs targeting Alcantara:
“The Marlins hold a $21 club option for Sandy Alcantara this offseason, and it’s a foregone conclusion that it will be picked up. Alcantara has routinely been connected to the Cubs over the past two years, and if the Marlins are going to trade him, time is running out. Rather than risk losing him for nothing after a shortened season, perhaps this is the offseason the Marlins actually make the trade.”
Chicago would have to give up another top prospect to the Marlins for Alcantara. One year of Alcantara, however, could arguably be worth the asking price.
Here’s the oddest Chicago Cubs trade idea of the offseason so far
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