The Chicago White Sox did not need another reminder that their rotation is unfinished. They got one anyway, and it arrived from the other side of town.
In a Bleacher Report ranking of free-agent landing spots for Shota Imanaga and Kevin Gausman, Tim Kelly placed the White Sox third among destinations for Imanaga, behind only the San Diego Padres and the San Francisco Giants.
Kelly’s case is straightforward: the Cubs may not be Imanaga’s only chance to stay in Chicago.
The South Side, he wrote, already has a young offensive nucleus in Miguel Vargas, Chase Meidroth, Munetaka Murakami and Tristan Peters, the kind of group that helps explain how a club that lost 121 games in 2024 reached the postseason two years later. Sean Burke and Davis Martin give Chicago a respectable one-two punch.
What the organization does not have, in Kelly’s view, is a slam-dunk starting pitching prospect close to the majors. A veteran left-hander who can take the ball every fifth day would be a practical way to chase a second straight October.
That framing fits the moment better than a splashy pursuit of a frontline ace. Imanaga, who turns 34 in September 2027, is not the pitcher who finished fifth in National League Cy Young voting in 2024.
That season looks more like an outlier now. What he did offer the Cubs after accepting their qualifying offer was volume: more than 30 starts, the first time he has reached that mark in his major-league career.
For a White Sox club that has climbed out of a historic hole without a finished rotation, innings have a value that pure stuff rankings sometimes miss.
The cross-town angle is the part that will travel. The Cubs declined a three-year, $57.75 million option on Imanaga last winter, then circled back with a one-year qualifying offer worth $22.025 million. He took it.
If he leaves this time, Chicago’s North Side gets nothing in draft compensation. Kelly ranked a return to Wrigley fifth on Imanaga’s list, behind the Nationals as well as the White Sox. The implication is not that Jed Hoyer has closed the door. It is that the relationship already has a clock on it.
None of this makes Imanaga a White Sox lock. San Diego essentially has to rebuild a rotation, and San Francisco could use a left-hander after trading Robbie Ray. Both markets can spend.
Guaranteed Rate Field is not Petco Park nor Oracle Park, and a multi-year deal for a pitcher entering his mid-30s is still a bet that the recent version, not the 2024 version, is the one who shows up.
It is still a sensible bet for a team trying to prove the postseason was not a one-year spike. Burke and Martin need a partner who has already survived a full major-league workload.
The lineup Kelly highlighted is young enough that a short-term rotation fix does not have to crowd out the next wave of arms. And if the White Sox are serious about staying relevant in 2027, shopping in the same market as the Cubs is no longer an act of rivalry theater.
It is roster construction. Imanaga does not have to be the best free-agent starter available to be the one who makes the most sense on 35th Street.
