Caleb Durbin Admits One Tough Feeling Watching Brewers Reach World Series

Caleb Durbin opens up about his bittersweet journey after being traded from the Brewers to the Red Sox just before his former team's historic World Series run.

Caleb Durbin spent last year as a meaningful piece of the Brewers’ rise. Now Milwaukee is headed to the World Series, and he’s watching from the other side after a February trade sent him to the Boston Red Sox.

The Brewers’ run to the Fall Classic has been emphatic. They rolled past the Los Angeles Dodgers in a four-game sweep on Thursday night, sealing a franchise-record 103-win season and punching their ticket to their first World Series in 42 years. Durbin, meanwhile, was already out of the picture, with Boston knocked out by the New York Yankees in the Wild Card Series before October really got going.

That makes Durbin an obvious figure of interest for both fan bases, and Alex Speier of The Boston Globe reported on Saturday that Durbin addressed Milwaukee’s postseason march. Durbin said it was "a little bit bittersweet. It’d be more bitter if I wasn’t super happy with where I was (with the Red Sox)."

Milwaukee has filled third base without him by leaning on a late-season platoon that includes former Red Sox bench player David Hamilton and Joey Ortiz. Hamilton even came through in Game 4 of the National League Championship Series, delivering an RBI single and a home run that helped turn a 6-4 win into a more comfortable finish.

Still, Durbin’s individual season stood out. He was better at third than anything the Brewers had there, finishing with 4.4 bWAR and earning a spot as a finalist for the Gold Glove Award in the American League. The numbers suggest he should win it.

And while Durbin has made clear he’s content with his new home, there’s still a strange edge to the story. His career has been an underdog journey from the start, dating back to when the fourth-round pick out of Division III Washington University in St.

Louis first got into the pro game. Watching that kind of team go on without him has to sting just a little, even if he’s happy where he ended up.

In Other News...

Payton Tolle Is Giving Red Sox Fans A Classic New Debate

Payton Tolles mustache has become part of the conversation in Boston almost as much as his pitching. Nick Offerman, the actor and comedian, brought Tolle up on a podcast and joked that he could pass for the young Red Sox pitchers father, thanks to the matching facial hair. Tolle took the attention in stride and answered with a playful post on social media, which only added to the growing sense that he is quickly becoming one of the more distinctive figures in the clubhouse.

For Red Sox fans, the fun part is that this is not just about the look. Tolles pitching performance has helped make him a name worth following, and the mustache comparisons naturally invite a little nostalgia for the long line of Boston players who became icons for theirs. The debate now is less about whether Tolle fits the look and more about where he belongs in that Red Sox tradition, a question that seems likely to keep getting louder as he keeps taking the mound. [Read more 🡒]

Red Sox Rotation Could Get Complicated Fast If Sonny Gray Walks

The Red Sox entered the offseason with a rotation that already looks unfinished, and Sonny Gray may only add to the uncertainty if his mutual option is declined. Boston has some internal answers in Brayan Bello, Tanner Houck and Kutter Crawford, but each comes with its own question marks, leaving the club in a familiar spot where upside and reliability do not quite line up cleanly.

If Gray moves on, the search for stability could quickly shift from contingency planning to priority work. Boston would then have to weigh the free-agent market for names such as Michael King, Freddy Peralta or Casey Mize, a reminder that one possible departure could ripple through the whole rotation picture before the winter really gets going. [Read more 🡒]

Brewers Trade That Shocked Fans Looks Bigger Than Ever Now

When the Brewers shook up their roster ahead of the 2026 season, the deal that sent Caleb Durbin, Andruw Monasterio, Anthony Seigler and a draft pick to Boston drew plenty of attention, especially with Kyle Harrison, David Hamilton and Shane Drohan heading back to Milwaukee. For the Red Sox, it was the kind of move that immediately invites scrutiny, because it came alongside Milwaukees other headline trade sending Freddy Peralta to the Mets and set up a season in which both clubs would spend plenty of time being judged against the return.

David Hamilton, in particular, has made the trade look even louder in hindsight, with a key playoff role helping fuel Milwaukees run. Harrison and Drohan have also been part of the Brewers regular-season and postseason picture, which only adds to the intrigue for Boston as the organization weighs what it gave up and what it got back. For a front office that has to think about both now and the years ahead, this is the sort of swap that can linger well beyond the first round of reaction. [Read more 🡒]