Report: Cubs Competing With White Sox for Same Free Agent

The Chicago Cubs need to add starting pitching. It could be an entire rotation that Jed Hoyer is tasked with replacing this winter.

Perhaps that means bringing back some of Chicago's arms that were lost to free agency. But for a team that hasn't had a good enough pitching staff to be true World Series contenders over the last couple of seasons, it could also be an opportunity for the Cubs to reshape the roster and get creative with some of their pitching additions.

Current reports indicate that the Cubs will not be involved in the sweepstakes for left-hander Tarik Skubal. Michael King also seems like a player who the Cubs don't see as an ideal fit. Those are two of the top names on the market, but it doesn't mean the Cubs won't still be looking to make a splash and add multiple arms.

I'd argue Chicago's lack of interest in the Skubal sweepstakes stems from the club's need for quantity as well as quality. The Cubs are not one pitcher away, and it may be better to spread their financial resources across three different free-agent arms with upside.

Just one problem. Chicago will have plenty of competition to actually land the players it covets. There are a lot of teams out there that need starting pitching, and the crosstown Chicago White Sox are reportedly one of the teams competing directly with the Cubs.

According to MLB insider Bruce Levine, one of the top priorities for the Cubs right now is Japanese right-handed pitcher Kaima Taira.

Taira has been both a starting pitcher and a relief pitcher in Japan's Nippon Professional Baseball. In 2026, playing for the Saitama Seibu Lions, he went 12-5 with a 1.36 ERA over 146 innings. His agent, Scott Boras, met with the Cubs and White Sox GM Chris Getz during the GM meetings in Las Vegas last week.

It's not hard to see why the Cubs have interest here. Taira has legitimate ace upside, but questions about whether he'll be a starting pitcher or a relief pitcher in Major League Baseball could drive down his price. That's not to say the Cubs are looking for a bargain on the free-agent market. But the goal should be to acquire as many frontline arms as possible. And if the Cubs land Taira on an affordable contract and cash in on his upside, it could be the key to restoring this starting rotation.

Age also seems to be a factor in the pitchers the Cubs are interested in. Trevor Rogers is one arm on their radar, and Taira, who's about to turn 27 years old, should have his prime years in front of him as he comes to the United States.

After both the Cubs and White Sox made the playoffs in 2026 for just the fourth time in history, the crosstown rivalry has now carried over into the offseason. If the Cubs want to land the starting pitchers they covet, they'll have to outbid other teams aggressively pursuing pitching, like the White Sox.