Perfect Cubs free agent fit comes off the board before offseason even starts

There's still a month left in the 2025 regular season and, beyond that, all signs point to the Chicago Cubs appearing in the postseason for the first time in a full-length campaign since 2018. But that doesn't mean it's too early to start thinking about the offseason.

The big story will, of course, be Kyle Tucker - and whether or not the Cubs act like the big market behemoth they are in a pursuit to re-sign him when he hits free agency. But there are other fits in this winter's free agent class, although one major name came off the board this weekend after signing a contract extension.

Aroldis Chapman and the Boston Red Sox agreed to a one-year, $13.3 million deal with a mutual/vesting option for 2027 that could push the total of the deal to $26 million over two years. The option vests at a certain innings threshold, although the specifics have not been made public.

Chapman, who turns 38 in February, has re-established himself as one of the game's premier closers this year in Boston, putting up numbers reminiscent of when he was in his prime a decade ago. He carries a 1.04 ERA and 1.83 FIP into action Sunday, driven by a vastly improved walk rate and his usual high strikeout numbers (74 in 52 innings).

The Red Sox also appear to be headed for a playoff berth, locked in a battle for a wild-card spot in the American League. Boston entered Sunday trailing the division rival Yankees by 1 1/2 games in the wild-card race, and up 2 1/2 on Seattle.

Cubs will need to focus on left-handed relief help this offseason

vAs for the Cubs, the fit is clear. On a short-term pact, Chapman made sense as an offseason target. Looking at the left-handers on the roster, Taylor Rogers, Drew Pomeranz and Caleb Thielbar are all free agents at season's end, leaving president of baseball operations Jed Hoyer a major southpaw shortage to address heading into 2026.

His age makes him a risk, but Chapman has been remarkably healthy in his career, given his fastball velocity that still averages triple digits even more than a decade-and-a-half into his big-league career. It would've been a big-ticket bullpen addition for Hoyer, who has long preferred to focus on reclamation projects and one-year bargain signings to round out his team's pen, but, at least on paper, there was a deal to be had here.

Now, the only way the Cubs will see Chapman next year is when Chicago and Boston close out the 2026 regular season schedule with a three-game set at Fenway Park.