As the World Series gets underway tonight, the Cubs have reason to keep a close eye on the teams fighting for the title. The Tampa Bay Rays and Milwaukee Brewers are playing for baseball’s biggest prize, and for a Chicago club headed into an offseason with pitching clearly on the mind, there are names in that matchup that matter beyond the trophy chase.
The most obvious one is Freddy Peralta. The Cubs are almost certainly going to be linked to him right up until he either retires or Craig Counsell is no longer in Chicago.
Peralta is set to hit free agency this winter, and after a rough start with the New York Mets, the Tampa Bay Rays may have helped get him back on track. There are still questions about how sustainable his success in Tampa really is, since the underlying numbers do not fully back it up, but the production itself is hard to dismiss.
Tarik Skubal and Sonny Gray are probably higher on the Cubs’ offseason board, but Peralta is absolutely part of the conversation.
Then there’s Dustin May, who doesn’t profile as the headline move for the rotation but could still fit if Chicago makes bigger additions first. May didn’t find much success with the Brewers after being traded by the St.
Louis Cardinals, yet he could make sense as a lower-stakes arm if the Cubs have already landed two established starters. In that setup, he becomes the kind of worthwhile gamble that helps round out a pitching-heavy winter.
Griffin Jax is another name worth noting. Long known as a reliever with the Minnesota Twins, the Tampa Bay Rays have used him in a different role, with 23 of his 34 appearances this season coming as starts.
He posted a 3.53 ERA and a 46% ground-ball rate, and his upper-90s fastball gives him exactly the kind of power stuff the Cubs tend to value. The other thing Chicago wants from any arm it adds is a profile that keeps the ball on the ground.
Jax checks two of those three boxes. He’s also entering his final year of arbitration, which makes this a logical time for Tampa Bay to move him while his value is still strong, especially with the possibility that the 2027 season could be shortened.
On the position-player side, Jake Bauers is probably more of a warning sign than a perfect fit. He’s the kind of bat the Cubs should be examining, even if he isn’t the actual answer.
Bauers has hit right-handed pitching well, and if Matt Shaw and Pedro Ramirez are part of the starting lineup, Chicago is going to need more help against righties. It may not come in the form of Bauers himself, but the need is real, and the Cubs can’t ignore that part of the roster this winter.
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Former Cubs Pitcher Ended Up With Championship Hardware Somehow
Jake Woodfords 2026 season turned into one of those odd baseball footnotes that players carry around long after the numbers are forgotten. He logged time with the Brewers, Cubs and Rays, bouncing through brief stretches with each club before Tampa Bays run carried all the way to a championship, giving him an unexpected World Series ring in the process.
For the Cubs, Woodford was only a small part of a larger season picture, but his path is a reminder of how quickly a pitchers year can change in the margins. He finished with 19 appearances and rough results overall, yet somehow still wound up with the kind of hardware most players spend a career chasing, even if his role in getting there was far from a headline-grabbing one. [Read more 🡒]