4 potential Cubs free agent fits - according to an MLB.com insider

The 2025 World Series kicks off this weekend between the Los Angeles Dodgers and Toronto Blue Jays - but for 28 other teams, including the Chicago Cubs, the focus has shifted to the offseason.

With Kyle Tucker headed for free agency and a bench and pitching staff that will need to be rebuilt, Jed Hoyer has plenty to do this winter. MLB insider Mark Feinsand broke down the top 30 free agents in this winter's class and identified the best fits for each.

Here are 4 players Feinsand views as great fits for the Cubs.

4 potential free agent targets for the Chicago Cubs

Kyle Tucker

Let's rip the band-aid off right away, shall we? Feinsand's top-ranked free agent, Kyle Tucker, is expected to command a long-term deal worth north of $300 million. Chicago has never come anywhere close to that amount on a free agent deal - so we're talking about completely uncharted waters for Hoyer and the Cubs.

In the first half, the Cubs were rolling - and Tucker was a huge reason why. Prior to the All-Star break, the star outfielder slashed .280/.384/.499, lengthening the lineup and elevating the play of everyone around him, especially Pete Crow-Armstrong and Seiya Suzuki.

Second-half injuries and slumps pushed the train off the tracks a bit, but there's still zero question. Tucker has the track record - and youth - to make him the most coveted name of the offseason.

Shane Bieber

Given how the Cubs' postseason journey ended, in part due to a lack of starting pitching, seeing Shane Bieber on the game's biggest stage this weekend will hurt.

The longtime Guardians right-hander was traded to Toronto at the deadline and he made seven regular-season starts for the Jays, pitching to a 3.57 ERA and 49.1 percent ground ball rate. The former AL Cy Young award winner could add a powerful right-handed compliment to the likes of Justin Steele, Matthew Boyd and (depending how his complicated contract situation plays out), Shota Imanaga.

With Tommy John surgery well in the rearview mirror heading into 2026, Bieber could be a hot commodity for teams looking to bolster their starting rotation this winter.

Ryan Helsley

Chicago needs out-getters. Period. With a bullpen poised to experience dramatic turnover, Hoyer will be tasked with re-shaping the late innings for Craig Counsell - and adding a flame-throwing ninth-inning arm certainly wouldn't hurt matters.

Ryan Helsley was a standout piece for the division rival St. Louis Cardinals for years, emerging as one of the game's premier closers in recent seasons. However, he imploded after being dealt to the New York Mets this summer, as his walk rate climbed, strikeout rate fell and opponents averaged 11 hits per nine against him down the stretch.

He was bad - really bad - but his track record before the move will still net him a strong market. The question isn't what his market will look like, but whether Hoyer will deviate from his standard M.O. and sign a reliever to a multi-year deal.

Kazuma Okamoto

Rounding out Feinsand's list, we find NPB slugger Kazuma Okamoto, who will be posted this winter. A corner infielder by trade, he's a big-time power bat (248 homers in 1,074 contests) and could be an intriguing addition for a team like the Cubs.

Rookie Matt Shaw was serviceable at the hot corner - well, he was elite defensively, but the bat left much to be desired. With limited ways to upgrade the offense, a big bat at third could be the route Hoyer takes, either via Okamoto or someone like Alex Bregman, who the team had major interest in last winter.

Given the Cubs' successful track record with players from Japan, could Okamoto be the next in line, joining the likes of Suzuki and Imanaga on the roster? It definitely seems like a possibility.