Monday, December 8, 2025

Top Free Agent Target Established for Cubs as Winter Meetings Begin

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The Winter Meetings are underway and the top free agent target has clearly been established for the Chicago Cubs. After bowing out of the Dylan Cease negotiations the front office now seems determined to sign a different hard-throwing righty as both local and national media continue to report that the Cubs are preparing a serious push for Japanese star Tatsuya Imai.

The 27-year-old starting pitcher was posted by his NPB team Saitama Seibu Lions back in November, opening up a negotiating window that concludes on Jan. 2. There has a lot of apprehension from the fan base when discussing potential free agent targets based on the Cubs’ track record in the past decade, but the Cease pursuit did confirm that Jed Hoyer does seem willing to pay up for a top-tier starting pitcher.

Imai entered the offseason as one of the top-three free agent starters and is projected to get between $135 million and $150 million or slightly more on a 5-7 year contract. He’s a few years younger than the other top starting pitchers in the higher tier of free agency, which is why he could ultimately sign a longer deal with the Cubs, who haven’t really shown the willingness to invest in longterm deals for pitchers.

But Imai’s talent is certainly intriguing and by the sound of it the Cubs are convinced the right-hander can flourish in the major leagues. On Monday, MLB insider Jon Heyman specifically mentioned the Cubs as one of the teams showing serious interest in Imai.

Meanwhile, Cubs beat reporter Patrick Mooney said in his Winter Meetings preview on Sunday that the Cubs will indeed play a part in Imai’s free agent process. Of course, the worry remains whether or not the Cubs will remain engaged in talks with Imai once other big-market clubs enter the negotiations and a bidding war commences. How much do the Cubs value Imai and will another team blow their offer out of the water?

That’s what reportedly happened at the end of November, when the Cubs did have serious interest in signing Cease, but exited those talks as opposing offers entered the $200 million mark. Cease ultimately signed a seven-year, $210 million contract with the Toronto Blue Jays in a deal that does include deferred money.

As a reminder, the Cubs are not hiding the fact that they are not going to offer deferred money to any potential free agent target, which could put them at a disadvantage when bidding against other teams.

The Cubs are going to sign a starting pitcher and if not they’ll trade for one this offseason. There’s no doubt about it, so how would feel about Imai being the No. 1 target now because the Japanese pitcher is the Cubs’ plan A at the Winter Meetings this week.

Aldo Soto
Aldo Soto
With a journalism degree from Eastern Illinois University and a decade of Cubs reporting, my work has appeared on 670 The Score, ESPN 1000, and the Pinwheels and Ivy Podcast. I cover Cubs news and analysis for Sports Mockery, including roster moves, game breakdowns, and prospect development.

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