It certainly looks like the Yankees’ rough offseason is far from over. If you remember, we’ve already talked about how their capped payroll has basically taken them out of the running for stars like Cody Bellinger or Kyle Tucker. And as Hal Steinbrenner has openly said, the team is trying to stay under a $300 million budget. Thus, chasing those high-priced names feels even more unrealistic.

As MLB insider Buster Olney put it, with their 2026 payroll already projected around $213 million, the Yankees just don’t look like big spenders this winter. But the twist? The Cubs are reportedly stepping in and doubling down on the very players the Yankees are still eyeing. A move that could shut the door on the Bombers’ offseason hopes altogether.

“It will be an active offseason,” The Athletic quoted Cubs’ owner Jed Hoyer. “We’ll be really active in the pitching market.”

And their activeness comes in the form of pursuing Michael King and Tatsuya Imai, the very two arms the Yankees are also eyeing.

Well, the Cubs clearly aren’t messing around when it comes to upgrading their pitching. They proved that when they made a run at Dylan Cease before he wound up with the Blue Jays. And why not? Chicago finished 2025 with the 8th-best ERA, but their rotation really stumbled in the NLDS, especially Matthew Boyd and Shota Imanaga.

So now, while King had already been linked to the Yankees, the Cubs have officially jumped into the chase. They are racing to get their hands on the starter who, despite having just 15 starts this year, still put together a 2.59 ERA and a 28% strikeout rate. But with King projected to fetch around $80 million, do you think the Yankees could afford that?

Then there’s Japan’s newest pitching star, Tatsuya Imai.

Notably, after three straight seasons with an ERA in the 2.30 range, he just posted his best year yet: a 1.92 ERA, a 27.8% strikeout rate, and only a 7% walk rate. So, the Yankees are definitely interested, even with his projected $157 million price tag. But as always, they’re moving slowly, and the Cubs are right there, ready to capitalize.

After what they learned from bringing in Shota Imanaga and Seiya Suzuki, Chicago knows exactly how to tailor its pitch to Japanese talent. So, whether or not the Cubs end up landing King or Imai, one thing feels clear: the Yankees’ offseason is slipping out of their control.

The Cubs’ offseason plan goes beyond pitching

While the Cubs are pursuing Michael King and Tatsuya Imai, their offseason targets go beyond these names. The next big name is Alex Bregman. After not extending Kyle Tucker, the Cubs need another reliable and experienced batter, which Bregman could offer.

As per Spotrac, Bregman could land a four-year deal worth about $112 million, which works out to $28 million a year. Now, while it’s still unclear whether that fits into the Cubs’ financial plans, the Cubs are saving $16.5 million from Tucker’s salary. Moreover, they’re believed to have somewhere between $45–55 million to spend.

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So, while the Cubs front office has made it clear that starting pitching is the top priority, they also need to find a way to replace the offensive punch Kyle Tucker provided. Not to forget, he posted an .841 OPS with a .464 slugging percentage. In comparison, Bregman’s .822 OPS this year would be the best to replace Tucker.

So, the Cubs definitely have a few big-name targets on their radar — it’s just a matter of how many they can realistically bring in.