As the offseason heats up, the Chicago Cubs find themselves at a pivotal crossroads in their pitching plans. Shota Imanaga, who was a key addition to the Cubs’ rotation last season, has until November 18 to decide whether he’ll accept the club’s qualifying offer. But all signs point toward a parting of ways, opening up a significant hole in the starting rotation-and raising some big questions about how the Cubs plan to fill it.

One name that’s now officially on the table: Tatsuya Imai.

The 27-year-old right-hander from Japan’s Seibu Tigers was approved for posting on Monday, making him eligible to sign with a Major League team this winter. Once the posting is made official, Imai will enter a 45-day window to negotiate with MLB clubs. And make no mistake-he’s expected to be one of the more sought-after arms in this year’s free-agent class.

While Imai might not carry the same level of hype that surrounded Yoshinobu Yamamoto a year ago, he’s still projected to command serious money-potentially around $190 million. That puts him squarely in the upper tier of available starters this winter and places him firmly on the Cubs’ radar. But targeting Imai and actually landing him are two very different things.

Here’s where it gets tricky for Chicago.

First, the price tag. The Cubs have historically been cautious when it comes to mega-deals for starting pitchers.

In fact, they’ve never handed out a $200 million contract, period. So even if Imai’s final number comes in just under that threshold, it would still represent a major leap for a front office that tends to favor short-term flexibility over long-term commitments-especially on the mound.

Second, the competition. The New York Yankees are already being viewed as the frontrunners for Imai, and they’ve been linked to the right-hander for months. If the Yankees decide to go all-in-and they often do when it comes to premium pitching-they could easily outbid a more conservative Cubs front office.

And then there’s the Scott Boras factor.

Imai will be represented by the super agent, and that alone complicates things for Chicago. While the Cubs and Boras did come together on a creative three-year deal for Cody Bellinger last offseason, that was a unique situation.

Bellinger’s market collapsed, and both sides found common ground on a short-term, high-upside pact. That’s not likely to be the case with Imai, whose market is expected to be aggressive and competitive from the start.

In all likelihood, the Cubs will need to pivot if Imai’s price climbs too high. That could mean targeting the middle tier of free-agent starters-arms that offer value without the same financial commitment-or working the trade market in search of a controllable ace. The latter may be the more appealing path, especially given the Cubs’ desire to build sustainable success without tying up massive dollars in risky long-term deals.

One thing’s clear: pitching is at a premium, and teams know it. That means the Cubs will have to be both aggressive and creative if they want to shore up their rotation heading into 2026. Whether that means taking a big swing on someone like Imai or finding value elsewhere, the front office has decisions to make-and soon.