Ahead of the 2026 MLB season, the Boston Red Sox and Milwaukee Brewers made a massive six-player trade on February 9.
This trade package included Caleb Durbin, Andruw Monasterio, Anthony Seigler, and a Competitive Balance Round B draft pick from the Brewers. The players Boston shipped away included Kyle Harrison, David Hamilton, and Shane Drohan.
Now former National League Rookie of the Year candidate with the Brewers, Caleb Durbin, makes his feelings very clear about just missing a World Series trip with his former team.
Caleb Durbin Says Former Team Milwaukee Brewers Reaching World Series Is ‘Bittersweet’
On Thursday, October 15, the Milwaukee Brewers reached the World Series for the first time since 1982. They defeated the high and mighty Los Angeles Dodgers in a clean–and vengeful– four to nothing sweep.
Current Boston Red Sox third baseman Caleb Durbin, was a part of the 2025 Brewers team that got swept by the Dodgers in 2025.
Durbin and the Boston Red Sox’s season got cut short in the AL Wild Card Series this season. Now that he’s had some time to reflect on the season, Durbin calls the Brewers trip to the World Series ‘bittersweet.’
“A little bit bittersweet,” Durbin said about the Brewers reaching the World Series. “It’d be more bitter if I wasn’t super happy with where I was (with the Red Sox).”
(via @alexspeier)
With the Brewers, Durbin slashed .256/.334/.387 with 11 home runs and 53 RBIs. He played a key role in their 2025 postseason, playing in all nine games.
It’s hard to move forward when Durbin was right there with the Brewers last postseason, however, he experienced the reversed outcome.
Did the Brewers Win the Caleb Durbin-Boston Red Sox Trade?
Caleb Durbin has cemented himself as a near-permanent replacement after losing Alex Bregman in free agency. He put up a 4.4 bWAR and is an American League Gold Glove finalist.
Since Durbin’s departure, Milwaukee installed a platoon of players rotating in and out of third baseman.
But did the Red Sox really win that trade?
Aside from the obvious, the Brewers reaching the World Series and the Red Sox watching at home, the players sent to Milwaukee have made a huge difference this postseason.
One of those players rotating at third base is David Hamilton, a former Red Sox bench player. This postseason, Hamilton is slashing .455/.500/.727 with an OPS of 1.227 and a game-sealing solo shot in the top of the ninth inning in Game 4 against the Los Angeles Dodgers.
Kyle Harrison has yet to make his postseason debut, but was the Brewers no. 2 starter for a good stretch during the regular season. He went 11-5 with a 4.20 ERA and 141 strikeouts.
Shane Drohan made his postseason debut after a pitching hiatus since September 27. He allowed one hit and one run in the first inning of Game 4. But was a staple piece in the Brewers rotation and bullpen whilst dealing with injuries.
While Durbin might be a better long-term investment, the Brewers got what they needed to ensure a trip to the World Series. They built around their already strong team, and got pieces just to fill in the gaps.
Ex-Brewer Caleb Durbin Sends 4-Word Message to Former Team After Red Sox Trade