Two Brewers free agent targets sign contracts elsewhere in wake of Caleb Durbin trade

Prior to Monday morning, the dominating discourse in Milwaukee Brewers world was that the team needed to add more starting pitching depth ahead of the 2026 season. Despite having a number of young rotation options, many of them are lacking experience and are therefore expected to have something of an innings cap in 2026. Paired with the fact that nearly all of the starting options are right-handed, many Brewers insiders expected the team to add a left-handed option to their starting staff in the near future.

Such a prediction came to fruition on Monday morning, but not in the way most Brewers fans were expecting. Rumors of the team reuniting with José Quintana or Jordan Montgomery or signing a different veteran southpaw led many fans to believe that any addition to the starting staff would come via the free agent market, not a surprising late-offseason trade. However, it was the latter that ultimately occurred; Matt Arnold and the Brewers front office swung a surprising deal with the Boston Red Sox to land two left-handed starters, Kyle Harrison and Shane Drohan, but parted ways with 2025 NL Rookie of the Year finalist Caleb Durbin in the process.

The nature of the trade was shocking, seeing as the Brewers also sent two other third base options to Boston in the deal, Andruw Monasterio and Anthony Seigler, but the front office did fulfill the writers' prediction of adding a lefty to the rotation mix ahead of the 2026 season. Not only is the deal likely to have a ripple effect in Brewers land -- fans are still waiting to see how Arnold and company will address the vacancy left at third base -- but it also has led to a pair of free agent signings around the league that seem to be directly related to Milwaukee's now lack of a need for a left-handed starting pitcher.

Late on Tuesday night, roughly a day and a half after the Durbin deal went down, Quintana landed a one-year contract with the Colorado Rockies, suggesting that he was waiting to see what avenue the Brewers went down before agreeing to a contract for the 2026 season. Now, roughly 48 hours after the Brewers and Red Sox' swap, another starter who was awaiting Milwaukee's decision has made up his mind in regard to his 2026 destination.

Jordan Montgomery follows José Quintana in officially leaving Milwaukee shortly after Brewers make different left-handed addition to their rotation mix

After joining the Brewers' organization at the 2025 trade deadline, despite knowing that he wouldn't be able to pitch for them, Montgomery reportedly built a positive relationship with Milwaukee's coaching staff. As a result, many viewed a reunion with Montgomery this offseason as a real possibility, regardless of the fact that the veteran southpaw is set to miss a few months of the 2026 season as he continues to rehab from Tommy John surgery.

However, once the Brewers added Harrison (and Drohan) to the mix, the chances of a reunion with Montgomery decreased significantly. Rather than go for a veteran stopgap in their rotation, Milwaukee elected to spend big for controllable lefties who can impact the roster for years to come.

Montgomery returns to the Texas Rangers, the team with which he won the 2023 World Series, on an incentive-laden $1.25 million deal. It's certainly a deal the Brewers could have afforded, as is Quintana's $6 million salary with the Rockies, but now that Milwaukee's rotation picture is set, and holes exist elsewhere on their roster, hopefully that money is being saved for an infield addition.

In the end, while Montgomery would have been an intriguing buy-low rotation candidate, and Quintana could have been a consistent innings-eater at the back-end of the Brewers' rotation, Milwaukee's need for either of them went out the door the second they executed the Durbin trade. Given the proximity of these two free agent deals to said trade, it's certainly possible that the Brewers viewed each of them as a potential back-up plan, and the two veterans were waiting for Milwaukee's decision before signing deals elsewhere.