It's been a while since the Chicago Cubs signed a top free agent starting pitcher and I'd say a few weeks ago I, along with a lot of other fans, had very little faith that the team would now target the upper tier of available arms to help bolster their rotation. Sure, there some early rumblings from Bruce Levine that the Cubs would have interest in Dylan Cease, then Bob Nightengale added some more fuel to the fire with his report that also pointed to the Cubs pursuing a elite starting pitchers in this year's free agent class.
Now, after a week at the GM meetings the possibility that the Cubs actually do sign a top free agent pitcher is suddenly becoming more realistic.
First, at The Athletic Cubs beat writer Patrick Mooney wrote the following when describing the team's goal this offseason. We all know that the Cubs have to upgrade their pitching staff, but the burning question remains how aggressive will they be and how much are they willing to pay for it?
Via The Athletic.
Given those needs, the Cubs are open-minded about that pursuit of pitching, looking at potential trades and a higher tier of free-agent starters than they have targeted in recent years, according to sources briefed on the team’s plans.
That little detail is certainly eye-catching because you have to go back to 2018, when the Cubs last signed a free agent starting pitcher to a contract worth more than $100 million. That was Yu Darvish, who agreed to a six-year, $120 million deal with the Cubs. In recent years the Cubs have added to their rotation through free agency, but the additions have come at the mid-tier level with guys like Marcus Stroman, Jameson Taillon and Shōta Imanaga being the main acquisitions.
Tatsuya Imai, the perfect Cubs transaction?
There's one name that has become a popular target among Cubs fans and the speculation intensified this week after ESPN's Jeff Passan named Japanese free agent Tatsuya Imai as the perfect move for the Cubs this offseason. Here's what the top MLB insider wrote at ESPN.
Via ESPN.
The perfect transaction: Even with Tucker expected to leave, the Cubs still have plenty of thump in their lineup. They will win or lose based on pitching, and their starting rotation needs help. The Cubs aren't the sort of team inclined to pay pitchers for past-their-prime years, and while that tends to be the sort of thing that's incompatible with free agency, there happens to be a 27-year-old available this winter who won't even cost a draft pick to sign. It's just money, and seeing as the Cubs don't spend a whole lot of that -- their current projected payroll is around $150 million -- now seems the right time to splurge a little.
Sign free agent right-hander Tatsuya Imai.
That brings us back to Levine, who was on Marquee Sports Network and discussed a potential pursuit of Imai with analyst Lance Brozdowski. Levine dropped this line at the end of the video, "I don't think they'd back away and I don't think the Cubs will be afraid to make a huge investment in Imai."
So, how much is the Japanese free agent predicted to earn as he comes over to MLB?
Tatsuya Imai contract projections
Kiley McDaniel (ESPN): 6 years, $135 million ($22.5 million AAV)
MLBTR: 6 years, $150 million ($25 million AAV)
Ben Clemens (FanGraphs): 5 years, $100 million ($20 million AAV)
Tim Britton (The Athletic): 8 years, $190 million ($23.75 million AAV)
The 27-year-old pitcher was amazing in 2025, posting a 1.92 ERA with a 27.8 K% in 24 starts. The 5-foot-11, righty struck out 178 batters in 163.2 innings a year after striking out 187 batters in 173.1 innings during the 2024 season.
Here's a quick scouting report on Imai from ESPN's Kiley McDaniel, who projects Imai as a strong No. 2 or 3, with ace potential.
Via ESPN.
A big selling point on Imai is his cratering walk rate, going from a BB/9 of 5.1 to 4.1 to 3.6 to 2.5 over the past four seasons, punctuated by his 2025 line: 163⅔ IP and a 1.92 ERA. Imai is 5-foot-11 and throws from a lower slot, so he creates a flat plane, excellent for swings and misses at the top of the zone for his 93-97 mph four-seam fastball that hit 99 mph last season. His miss rate on the pitch wasn't elite because he didn't throw it at the top of the zone very often, but that's something that can be fine-tuned in the big leagues.
Imai has an above-average splitter, but his slider is a more interesting topic. His slider doesn't slide: It averages arm-side movement, like Trey Yesavage's, so it can be an effective pitch even if it's unusual to see (especially when paired with a splitter and above-average fastball velocity, like Yesavage does). There's some conventional wisdom that a backup slider is the best pitch in baseball (because nobody knows when a pitcher will misthrow the pitch like that), but that's meant as a one-off, not a recurring quality to shoot for.
Given his age, recent track record and pitching arsenal, it's clear why Imai is viewed as one of the top free agents available this offseason. The Cubs have had success bringing in talent from Japan, but this would definitely be a change of pace for Jed Hoyer's front office that has strictly shied away from top-tier free agent pitchers.
But considering the team's massive gap below the luxury tax, maybe this will finally be the time they do pursue a talented pitcher like Imai, who will end up with one of the highest free agent contracts heading into the 2026 season. Imai, who is represented by Scott Boras, will be officially posted on Nov. 19. He will then have 45 days to sign a deal with an MLB team.
Will it be with the Cubs?
