MLB insider reveals this player almost wasn't included in Brewers and Red Sox' offseason trade

After a three-hit game in last night's win over the Seattle Mariners, Caleb Durbin's batting average eclipsed the Mendoza Line (above .200) for the first time in the 2026 season. Following a brutal start to the campaign for the 2025 NL Rookie of the Year finalist, Durbin is finally starting to come around, with an .877 OPS in the month of June to prove it.

Even still, Durbin, who the Milwaukee Brewers traded to the Boston Red Sox back in early February, has plenty of work to do to make the offseason swap look like a good decision from Craig Breslow and the Red Sox' front office. The Brewers sent Durbin, infielders Andruw Monasterio and Anthony Seigler, and the 67th pick in the 2026 MLB Draft to the Red Sox, and in exchange received left-handed hurlers Kyle Harrison and Shane Drohan, as well as infielder David Hamilton.

Given the success that Harrison alone has demonstrated this season, Durbin exceeding the value of one of the best young starting pitchers in the National League, who also happens to be a southpaw and under team control for four more seasons after 2026, feels unlikely. Add Drohan and Hamilton's production into the fold, and the Brewers appear to have "fleeced" the Red Sox by trading three infielders and a draft pick for a better infielder and two controllable left-handed starters.

However, as reported by MLB insider Ken Rosenthal earlier this week, the initial trade structure that the Brewers and Red Sox had in place this past offseason looked much different than what the two teams ended up agreeing on. In an article for The Athletic, Rosenthal wrote, "The Brewers originally targeted only Drohan and left-hander Kyle Harrison for Durbin, according to a person briefed on the discussions. After deciding they also wanted infielder David Hamilton, they expanded the package, sending the Red Sox infielder Andruw Monasterio, outfielder Anthony Seigler and their competitive balance pick, 67th overall, as well."

David Hamilton's eventual inclusion in the Brewers and Red Sox' offseason swap makes deal look even better for Milwaukee

According to Rosenthal, the Brewers were initially hoping to acquire both Harrison and Drohan for Durbin alone. Whether or not the Red Sox were actually ready to agree to a trade of that nature is still unknown, but assuming they were, Milwaukee made a wise decision in electing to include Hamilton in the deal as well.

Hamilton, though he hasn't necessarily broken out in the way Pat Murphy was expecting him to, has been a key part of the Brewers' roster through the first three months of the season. Given the early-season struggles of both Joey Ortiz and Luis Rengifo, Hamilton was thrust into a far larger role than the Brewers were likely expecting him to play. Had Milwaukee agreed to the initial structure of the deal, the role that Hamilton ended up filling would have likely been assumed by Monasterio, who has -0.2 bWAR at this point in the season. Hamilton, meanwhile, has 0.8 bWAR, meaning the Brewers gained a full Win Above Replacement by opting for Hamilton over Monasterio.

Additionally, Hamilton has been just as valuable as Durbin (0.9 bWAR) through the first three months of the 2026 season, meaning the Brewers essentially acquired Kyle Harrison and Shane Drohan for the value of Monasterio, Seigler, who is back in Triple-A after a brief stint in the big leagues, and the 67th overall pick. While acquiring just Harrison and Drohan for Durbin would have looked mighty fine as well, having someone like Hamilton to fill in for Durbin on the left side of the infield was certainly worth the late modification to the trade.

Durbin's value is likely to continue increasing, but it's hard to imagine him matching the value of Harrison, Drohan, and Hamilton as all four players play out their remaining years of team control before free agency. The deal could start to look better for Boston if the 67th pick in this year's draft pans out in a major way, which would have the Brewers kicking themselves for expanding the deal to include Hamilton. However, given the stacked nature of Milwaukee's farm system, surrendering one draft pick to make sure this deal got over the finish line is a decision they would likely make 100% of the time.

Overall, either iteration of the eventual offseason blockbuster would have favored the Brewers to this point in the season, but acquiring someone like Hamilton, who has essentially replaced the value that Durbin would have offered, makes the deal look even better for Matt Arnold and Milwaukee's front office.

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