With Tatsuya Imai nearing a decision, the Chicago Cubs face growing pressure as the White Sox enter the race to sign him.
Chicago Cubs fans have waited all offseason for the front office to land a true frontline starting pitcher.
After being linked to Dylan Cease, that dream ended quickly when he signed a seven-year, $210 million deal with the Toronto Blue Jays and it was on to the next.
Then came the Zac Gallen buzz — a rumor that turned out to be complete fiction. Not only was Gallen not close to a deal with the Cubs, he was literally getting married when the report surfaced. As the calendar inches toward the new year, he remains unsigned.
So far, it’s been a lot of talk from the Cubs, with little action. Plenty of rumors tie them to the top starting pitchers on the market, and even some premier offensive names like Alex Bregman. But when it comes to deals actually getting done, the additions have been modest — depth pieces meant to fill complementary roster holes.
The Cubs brought in Tyler Austin from Japan to serve as a bench power bat and right-handed platoon option for Michael Busch. They got great value. Signing Jacob Webb to bolster the bullpen could end up being one of the quiet bargains of the entire offseason.
Between Webb, Phil Maton, Hoby Milner, Hunter Harvey, and the return of Caleb Thielbar, Jed Hoyer has done exactly what he set out to do: build a deep, reliable bullpen. You won’t find Cubs fans complaining about that.
But Chicago is still missing the splash.
That’s become an expectation in recent years, and especially this winter. Given the Cubs’ financial flexibility relative to other big-market teams — and the state of the organization after reaching the playoffs in 2025 — there should be nothing standing in the way of spending top dollar to address their biggest needs in a headline-grabbing way.
For weeks now, the Cubs have felt like the frontrunner to land Japanese right-hander Tatsuya Imai. That would be the kind of splash signing that meets the expectations of fans.
Chicago needs another righty to balance the rotation, and there isn’t a pitcher on the market with more upside. Imai is 27 years old and coming off a dominant season in Nippon Professional Baseball, where he posted a 1.92 ERA.
Now, he's looking for a new team in MLB. And the clock is ticking.
Imai must have a contract finalized by Friday afternoon, which means an agreement will likely need to be in place by Thursday at the latest. He’s in the United States this week meeting in person with three or four finalist teams before making his decision.
And just as that decision nears, the Cubs received worrisome news: the Chicago White Sox are emerging as a serious contender?
The White Sox already made waves before Christmas, stunning the baseball world with a two-year, $34 million deal for Japanese slugger Munetaka Murakami. Frankly, I thought Murakami made a ton of sense for the Cubs as well — a Kyle Schwarber-type offensive upside at a fraction of the cost, and a potential hedge against losing Kyle Tucker’s production down the line.
Instead, the Cubs watched while the White Sox closed.
No reason to panic just yet. But the Cubs can’t let this happen again — not with a player like Imai, who Cubs fans have been rallying around for months.
The fan base is already uneasy with how this offseason has unfolded. It doesn’t sit right that a rebuilding White Sox team — one that lost over 100 games for a third straight season in 2025 — could outspend the Cubs while they're supposed to be pushing toward a World Series window.
Try to make that make sense. You can’t.
That’s the reality right now. Lose Imai — the best fit among all remaining free-agent starters — to the White Sox, and the backlash will reach a new level.
Sure, it’s possible the White Sox chatter is nothing more than a leverage play from Scott Boras. That’s always on the table. But given the Murakami deal and the momentum that comes with it, the threat feels real. And the question becomes simple: Are the Cubs really willing to take that risk?
Imai’s market has clearly cooled. Teams appear hesitant to commit to long-term deals, likely due to questions about whether his 2025 season was a true breakout or an outlier. There’s no doubt he can be a solid MLB starter — but is he worth $150 million? Is he the type of arm you trust with the season on the line?
Those are fair questions, and it’s understandable if the Cubs want to be cautious. Getting this move right matters and there's always the trade market as a fallback option. But that hesitancy is exactly why Imai is now open to shorter term deals — and why the White Sox have suddenly entered the picture.
From where I’m sitting, this is a risk worth taking. The Cubs aren’t strapped for cash. They have plenty of starting pitching depth. And if it doesn’t work, they can absorb the miss far more easily than the fallout that would come from watching Imai choose the South Side.
Especially when you factor in the optics.
Jed Hoyer can’t let it happen.