1 off-the-wall Cubs trade with each division rival that would be mutually beneficial

I know that the odds of the Milwaukee Brewers and Chicago Cubs getting together on a trade right now is probably not going to happen. But instead of simply writing off teams as potential trade partners this offseason right out of the gate, I wanted to at least go around the horn and see if there were deals that might make sense for both sides.

The division (and the entire National League, for that matter) runs through Milwaukee. That much is clear. But an aggressive offseason could put the Cubs on solid footing as they look to punch back after a disappointing showing in 2026.

4 hypothetical NL Central Cubs trades that could help everyone involved

Milwaukee Brewers

The Brewers seem highly likely to trade Trevor Megill this winter. They have an embarrassment of bullpen weapons and have followed this playbook successfully for years, trading top-tier players on expiring contracts and building a pipeline of sustainable talent. A deal centered around Jaxon Wiggins or Cade Townsend would give Milwaukee a young arm they can develop, while solving the Cubs' ninth-inning question (at least for one year) with the return of Megill.

Cincinnati Reds

The Cubs need left-handed pitching and Nick Lodolo could be a low-risk option to round out the rotation or fill the swing-man role held by Colin Rea in recent years. He ranked near the top of the league in chase and walk rates in 2025 and a return to form isn't out of the question. Best part is he won't cost a blue-chip prospect. Mid-level talent should be enough to get this deal done.

St. Louis Cardinals

The Cubs and Cardinals hardly ever get together on trades, but for the sake of the exercise, let's do this thing. Alec Burleson just had a monster year for the Redbirds and has been a rumored trade candidate, but you're sacrificing defense if you put him back in the outfield. Maybe something centered around Kevin Alcantara gets a conversation started?

Pittsburgh Pirates

Here we go. Let's circle back on a deal we've talked about before. Mitch Keller has two years left on the extension he signed with the Pirates in 2024 and is coming off an injury-shortened 2026 campaign. His price tag could be down and the Cubs could be a perfect landing spot for the right-hander, especially if they're willing to eat all the remaining money and send a package including guys like James Triantos and Brooks Caple to Pittsburgh?

Add us as a preferred source on Google

Follow