Cubs' biggest rival just boldly traded Caleb Durbin for a questionable return

The Milwaukee Brewers have a recent history of coming out on the right side of big trades. They've built one of the healthiest organizations in all of baseball, capitalizing on returns for star players on expiring contracts, culminating in a pipeline of young, controllable talent ticketed for Miller Park.

Monday's trade doesn't fit into that bucket - this time, the Brewers sent a highly promising young player to Boston in Caleb Durbin, bringing back controllable pieces in return. The 2025 NL Rookie of the Year finalist played a key role for Milwaukee last season, with defensive versatility and top-tier bat-to-ball skills.

The full trade breaks down as follows:

Brewers bolster rotation, but now have a major hole in the infield

On the heels of this winter's Freddy Peralta trade, Milwaukee adds to its rotation with the addition of former top-100 prospect Kyle Harrison. He's yet to deliver on the promise that followed him in the minors, but at age 24, there's still time for him to put it all together - and the Brewers' track record of developing arms bodes well there.

But unloading Durbin, who perfectly fits the Brewers' hard-nosed, grinder personality and wholly embraced what it meant playing in Milwaukee, is a move that will raise some eyebrows. It leaves a gaping hole at third base, where Durbin spent most of 2025, with Fangraphs projecting infield prospect Jett Williams as the starter.

Williams came over as part of the Peralta trade, but has no big-league experience to his credit. Still, if Milwaukee can piece it together in the short-term, their top four organizational prospects are all infielders - and all four of them land in MLB Pipeline's recently-updated top 100. They seem to be betting their answer lies there, which, in their eyes, made Durbin expendable.

And keep in mind, the guys who were behind Durbin on the Brewers' depth chart were also sent to Boston in Andruw Monasterio and Anthony Siegler. Milwaukee looks thin, to say the least, at third - but the future on the dirt remains bright.

As the Cubs look to unseat the Brewers atop the NL Central, this move and its impact will definitely be worth keeping an eye on - both in spring training and throughout the regular season.