When the Milwaukee Brewers and the Boston Red Sox completed a six-player trade during the offseason, the move generated plenty of discussion around Major League Baseball. At the time, many analysts viewed it as a deal that could benefit both organizations, with each club addressing different needs as they prepared for the 2026 season. However, as the campaign approaches its midpoint, the trade is increasingly being viewed as a significant win for Milwaukee.
Back in May, MLB Network insider Joel Sherman praised the Brewers’ front office for its work during the winter, even going so far as to label the transaction the best trade of the entire offseason. Milwaukee acquired infielder David Hamilton, promising young starting pitcher Kyle Harrison, and left-handed pitcher Shane Drohan from Boston. In exchange, the Brewers sent infielder Andruw Monasterio, infielder Caleb Durbin, and former first-round draft pick Anthony Seigler to the Red Sox.
At the time of the trade, opinions were divided regarding which team gained the greater advantage. Harrison was considered a talented young pitcher with significant upside, but there were questions about whether he could consistently perform at a high level in a starting rotation. Hamilton offered speed and versatility but was still looking to establish himself as an everyday contributor. Drohan was viewed as a developmental pitching prospect with potential but had not yet proven himself at the major-league level.
On the other side, Boston acquired several players who were expected to strengthen organizational depth. Durbin was regarded as a contact-oriented infielder with offensive upside, Monasterio provided valuable infield versatility, and Seigler represented a former top prospect whose career still carried some intrigue despite an inconsistent path through professional baseball.
As more details have emerged about how the deal came together, it has become clear that the original discussions looked much different from the final agreement.
According to MLB insider Ken Rosenthal of The Athletic, writing on Friday, the Brewers initially had a far more focused objective. Sources familiar with the negotiations indicated that Milwaukee’s original interest centered primarily on two pitchers: Kyle Harrison and Shane Drohan.
Rosenthal reported that Milwaukee originally sought only those two left-handed arms in exchange for Caleb Durbin. The Brewers believed both pitchers could strengthen their pitching depth and potentially contribute at the major-league level. Harrison, in particular, possessed the kind of talent that made him an attractive target for a club known for developing and maximizing pitching potential.
However, as negotiations progressed, Milwaukee’s front office identified another player they wanted to acquire. The Brewers became increasingly interested in David Hamilton, whose speed, defensive flexibility, and athleticism fit the organization’s philosophy. Once Milwaukee decided Hamilton was a player worth pursuing, the framework of the deal expanded significantly.
To make the larger trade possible, the Brewers added additional pieces to their side of the transaction. Along with Durbin, they included Andruw Monasterio, Anthony Seigler, and the organization’s Competitive Balance Round draft selection, which was the 67th overall pick. The inclusion of that draft asset represented a meaningful addition to Boston’s return package and helped finalize the blockbuster agreement.
At the time, the expanded deal appeared relatively balanced. The Red Sox received multiple players who could contribute either immediately or in the future, while Milwaukee secured three players it believed could make an impact at the major-league level.
Several months later, however, the early results have strongly favored the Brewers.
The biggest reason for that assessment has been the emergence of Kyle Harrison as one of the National League’s most effective starting pitchers. Harrison has not simply performed well; he has developed into one of baseball’s premier young arms and has positioned himself as a legitimate contender in the National League Cy Young Award race.
Entering Friday’s games, Harrison owned an impressive 8-1 record while posting a sparkling 2.47 earned run average. He had also recorded a 1.09 WHIP and accumulated 80 strikeouts in just 65⅔ innings across 13 starts. Those numbers place him among the most productive and efficient starting pitchers in the league.
What makes Harrison’s performance even more valuable for Milwaukee is the consistency he has displayed throughout the season. Rather than relying on a handful of dominant outings, he has regularly provided quality starts and helped stabilize the Brewers’ rotation. His ability to miss bats while limiting baserunners has transformed him into a cornerstone of Milwaukee’s pitching staff.
For a franchise that has built much of its recent success around strong pitching development and efficient roster construction, Harrison’s breakout has been particularly significant. His emergence has strengthened a rotation that was already viewed as competitive and has given Milwaukee another frontline arm capable of matching up against elite opponents.
While Harrison has received the most attention, the Brewers have also benefited from meaningful contributions from the other players acquired in the trade.
David Hamilton has provided versatility and athleticism across the infield while contributing valuable depth to Milwaukee’s roster. His speed on the bases and defensive flexibility have allowed the Brewers to deploy him in a variety of situations. Although he may not be producing eye-popping statistics, his overall impact has been noticeable and has helped strengthen the club’s lineup and bench.
Similarly, Shane Drohan has delivered solid performances that have justified Milwaukee’s interest in acquiring him. Whether as a depth option or contributor on the pitching staff, Drohan has provided additional value that further tilts the trade in the Brewers’ favor. The combination of Harrison’s star-level production and useful contributions from Hamilton and Drohan has given Milwaukee a significant return on its investment.
The results have been reflected in the standings as well. The Brewers have enjoyed an outstanding start to the season, compiling a 45-27 record that has placed them atop the National League Central division. While many factors have contributed to that success, the players acquired from Boston have undoubtedly played an important role in helping Milwaukee establish itself as one of the league’s top teams.
Meanwhile, the Red Sox have yet to receive the level of production they hoped for from the players they acquired.
Caleb Durbin, who was viewed as one of the key pieces in Boston’s return, has shown signs of improvement in recent weeks. His performance has trended upward after a slow start, offering some encouragement that he could still become an important contributor moving forward.
Nevertheless, the overall numbers remain underwhelming. Through 65 games and 229 plate appearances, Durbin has hit just four home runs while driving in 27 runs. He has posted a .192 batting average, a .251 on-base percentage, and a .322 slugging percentage. Although there have been flashes of offensive potential, those statistics fall well short of expectations for a player who was expected to provide consistent offensive production.
The Red Sox remain hopeful that Durbin’s recent improvement signals a turning point rather than a brief hot streak. Given his age and developmental profile, there is still time for him to establish himself as a productive major-league player. However, his current output has not come close to matching the value Harrison has delivered for Milwaukee.
Andruw Monasterio has also contributed for Boston, though his impact has been relatively modest. The versatile infielder has appeared in 40 of the team’s first 72 games, serving in a utility role and providing depth across the infield.
Offensively, Monasterio has recorded two home runs and 11 RBIs while posting a .234 batting average, a .280 on-base percentage, and a .378 slugging percentage. Those numbers reflect a serviceable contributor rather than a difference-maker. While Monasterio has provided roster flexibility and occasional production, he has not emerged as a major factor in Boston’s lineup.
Anthony Seigler’s season has largely unfolded in the minor leagues. The former first-round draft pick has spent most of the year with Triple-A Worcester, where he continues to work toward earning a larger opportunity at the major-league level. Although he received a brief call-up in early June, appearing with the Red Sox for a two-game stretch, he has not yet established a consistent presence in Boston’s big-league roster.
As a result, the overall return package for the Red Sox has yet to generate significant impact at the major-league level. Durbin has struggled offensively, Monasterio has provided only modest production, and Seigler remains primarily a minor-league player.
While it is still too early to declare a final verdict on the trade, the early results strongly suggest that Milwaukee has gained a substantial advantage. Harrison’s transformation into a potential Cy Young candidate alone would make the deal appear favorable for the Brewers. When combined with the contributions of Hamilton and Drohan, the transaction increasingly looks like one of the most successful moves executed during the offseason.
For Boston, there is still hope that the long-term picture could improve. Durbin could continue his recent progress, Monasterio may remain a useful depth piece, and Seigler could eventually carve out a role in the major leagues. Additionally, the draft pick acquired in the trade could develop into a valuable asset in the future.
However, based on what has transpired during the first half of the season, Milwaukee appears to have secured a clear victory. The Brewers targeted players they believed fit their organization, expanded the trade to acquire an additional contributor they valued, and have already received major returns from those decisions. As the season continues, the trade stands as a testament to the Brewers’ evaluation process and may ultimately be remembered as one of the defining transactions of the 2025-26 offseason.
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