The Yankees look like they’re catching their breath this offseason. Yes, they’re still in the mix for a few big-name targets, but the clock is definitely ticking for them to make something happen. And one situation that’s starting to feel more urgent involves one of the Japanese pitchers on their radar, especially with the Dodgers already setting the bar high after landing Yoshinobu Yamamoto.

So, for the unversed, Tatsuya Imai has emerged as one of the most intriguing arms on the market and is drawing serious interest across the league. With a decision expected in the next couple of weeks, speculation is ramping up about where he’ll end up pitching in 2026. But while the Yankees are very much in the conversation, they’re now served with an ultimatum to make things work in reality.

“The Yankees are much in need of a starting pitcher right now, and this can only help them out, too. I’d love to see the Yankees go after Imai because he solidifies that first April-May before Rodon and Cole come back. Even when they come back, you never know, we saw guys come back and maybe weren’t necessarily their best selves,” a snapshot from the December 20 episode of Foul Territory offers a view of the Yankees’ contention for Imai.

Well, there’s a clear reason why Tatsuya Imai is generating so much buzz. Last season in Japan, he went 10–5 with a stellar 1.92 ERA across 24 games, logging 163.2 innings. And those numbers alone make him an attractive option, and for the Yankees, the fit feels especially logical right now.

Brian Cashman was already expected to add another starter this offseason, and that need has only grown.

For instance, Gerrit Cole, who missed the entire 2025 season following Tommy John surgery, still doesn’t have a firm timetable for his return. On top of that, Carlos Rodón could also miss Opening Day after undergoing a procedure, according to ESPN. And even when both pitchers do return, there’s no guarantee they’ll immediately be at full strength.

That makes a high-end arm like Imai feel less like a luxury and more like a necessity!

The problem, though, is the competition. The Cubs are very much in the hunt, and Marquee Sports Network’s Lance Brozdowski has suggested that Chicago may be willing to stretch beyond its usual comfort level in both years and dollars to land Imai.

With his projected deal not expected to exceed $200 million, and with the Cubs having freed up significant payroll after moving on from Kyle Tucker, the pressure is on. If the Yankees want Imai, it’s starting to feel like a now-or-never moment.

The Yankees’ bullpen is much more concerning

If the Yankees’ rotation feels shaky without Carlos Rodón and Gerrit Cole, the bullpen situation might be even more alarming. And honestly, we’ve seen this script before. Remember how the bullpen was a real problem last season. Yankees relievers finished with a 4.37 ERA overall, which ranked 23rd in the league!

And things somehow got worse down the stretch.

Reportedly, after August 1, when Cashman tried to fix the bullpen by bringing in David Bednar, Camilo Doval, and Jake Bird, the revamped group posted a 4.74 ERA, good for just 26th in MLB.

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Now fast forward to this offseason, and the concern level is even higher.

With Devin Williams and Luke Weaver no longer in the picture, adding new bullpen arms isn’t a luxury anymore, but a necessity. But the problem is that most of the dependable relief options, like Edwin Díaz, Tyler Rogers, and Kyle Finnegan, have already landed elsewhere. So, once again, the Yankees find themselves staring at a now-or-never situation, and when you stack everything up, the bullpen might actually be the bigger worry than the starting rotation.