Cubs suddenly get perfect chance to reunite with Kyle Schwarber

The Chicago Cubs may not have planned for nostalgia this winter, but the path is starting to point that way. Ten years after Kyle Schwarber helped deliver the 2016 World Series, MLB.com columnist Will Leitch suggested it as a nice reunion story.

But the idea of a return to Wrigley Field isn’t just a feel-good talking point; it’s an increasingly realistic solution for a team that still needs left-handed power.

And with Kyle Tucker expected to land elsewhere, Schwarber suddenly looks like the most attainable middle-order bat on the market.

Chicago needs impact offense, and there aren’t many safer bets than Schwarber’s combination of power and on-base ability. He led the National League with 56 home runs in 2025 and remains one of MLB’s most reliable DHs. Plugging him behind Seiya Suzuki and Pete Crow-Armstrong would lengthen a lineup that sagged in high-leverage spots last season.

He also knows the market, the ballpark and the expectations. Schwarber was one of the most dangerous hitters on the 2016 roster, and he’s only become more polished since leaving Chicago. For a team pushing toward contention, familiarity is a feature, not a flaw.

Schwarber’s next deal is expected to land around three years and $90 million, possibly more. He carries a qualifying-offer penalty, but he won’t require the decade-long commitment Tucker is seeking. For a front office trying to make a meaningful upgrade without tying its payroll into the 2030s, Schwarber is the rare elite bat who offers short-term impact without long-term risk.

The Cubs want a middle-order threat. They also want flexibility. Schwarber checks both boxes.

Jed Hoyer hasn’t shown his full hand, but Chicago has been aggressive on pitching and cautious with position-player spending. That often signals a surgical strike for the right lineup piece.

Schwarber is that piece.

He fits the timeline, the budget and the offensive profile. He fits the clubhouse. And he fits the fanbase, which still remembers him as one of the players who helped break the curse. 

It would give the lineup instant credibility and playoff-ready power. It would add a veteran hitter with a track record of big-stage production. And yes, it would bring back the memories — but this isn’t about nostalgia anymore.

It’s about fit. And right now, Schwarber might fit the Cubs better than any star available.