The Chicago Cubs have been relatively passive this offseason so far, much to the dismay of fans and media who would like a more aggressive approach to filling roster holes.
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When it comes to picking up a closer, the team has just about crapped out entirely, with the Rays’ Pete Fairbanks being the only true free agent high-end closer still available. They were reportedly in the running for Devin Williams and had shown interest in both Ryan Helsley and Emilio Pagan, who all signed elsewhere.
When it comes to starting pitching, there are several good options still on the market, although losing the bidding war for Dylan Cease early on in the free agent chase was a bit of a reality check.
The best is yet to come this offseason?
Chicago Cubs Chairman Tom Ricketts (R) smiles next to Chicago Cubs President of baseball operations Jed Hoyer (L) before a baseball game between the Chicago Cubs and Cincinnati Reds at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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So far, aside from the signings of Phil Maton and Hoby Milner and the re-signing of reliever Caleb Thielbar, Chicago is getting more press for what they MAY still do as names gradually get snatched up and the holidays approach.
However, in a recent piece written for The Athletic, former MLB general manager Jim Bowden gave a shot of hope to a disappointed Cubs fan base. He named two of the top talents in the free agent class of 2026 as “best fits” for the Cubs.
Alex Bregman and the Cubs?
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox third baseman Alex Bregman (2) runs the bases and watches his three run home run against the Minnesota Twins in the fifth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Third baseman Alex Bregman is one of those big names.
Per Bowden:
“Bregman is looking for a long-term commitment like Schwarber and Pete Alonso just received. His best shot to get that at this point would be with the Cubs, who will be trying to replace Tucker in the lineup. The Cubs covet Bregman’s leadership and mentorship of younger players. If they were to sign him, they could move Matt Shaw to second base and trade impending free agent Nico Hoerner or just move Shaw to the outfield.”
Bregman is most definitely the kind of player the Cubs adore. In many ways, he’s the kind of star Chicago was hoping for when they traded for Kyle Tucker last season– multifaceted, but with team leader capabilities. He also makes sense as a foundational piece for a Cubs team set to likely lose many of their top veterans via free agency (Ian Happ, Nico Hoerner, Seiya Suzuki, Carson Kelly, Matthew Boyd, Jameson Taillon, and Shota Imanaga) after next season.
The sticking point, of course, will be money and years. ESPN is projecting Bregman to land a contract of $170 million over five or six years. It’s not an obscene amount of money, considering what he would bring to the table, but giving so many years to a player who will be 32 by opening day is certainly not in character with the Cubs’ usual spending pattern.
Tatsuya Imai and the Cubs?
South Korea v Japan – Asia Professional Baseball Championship Final – Tatsuya Imai, Cubs via CubbiesCrib.com
Bowden also spotlighted Japanese pitching import Tatsuya Imai as the other best free agent fit for Chicago.
Per Bowden:
“The Cubs would like another starter and they could certainly use a younger option since three-fifths of their rotation is over 34 years old (Matthew Boyd, Jameson Taillon and Colin Rea), making Imai a particularly good fit in Chicago.”
The 27-year-old’s numbers in Japan practically scream at you.
In 2025, pitching for the Saitama Seibu Lions, Imai posted a 1.92 ERA and 178 strikeouts in 163.2 innings. Since 2022, the righty hasn’t turned in an ERA above 2.70 and he’s widely regarded as one of the most dominant pitchers in Japanese baseball.
For the Cubs, who are looking for a power pitcher who misses bats, Imai could be the guy, especially among the current crop of available starters.
ESPN’s projected 6-year, $135 million contract (which could actually be a low estimate) may turn off the conservative Cubs, especially considering the risk involved in signing someone to such a long, lucrative contract when they’ve never actually pitched in the major leagues.
But the Cubs do have a good recent track record with Japanese players and a Japan-friendly internal infrastructure, with Imanaga and Suzuki around as support for at least for one more season.
In a perfect world where Bregman and Imai come aboard, who could complain? Even getting one or the other would represent a big, bold step forward for the Cubs. It would be proof positive that ownership is actually interested in winning and not in just being good enough to keep Wrigley Field full and Marquee Sports Network subscriptions flowing.
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