With only a few weeks until Spring Training officially began, the Boston Red Sox and Milwaukee Brewers made a big-time trade that sent 2025 National League Rookie of the Year finalist third baseman Caleb Durbin to Boston in exchange for a package centered on starter Kyle Harrison. As the Brewers prepare to take on the Tampa Bay Rays in Game 1 of the World Series on Friday night, we look back at the deal that helped shape both the Red Sox's and the Brewers' rosters. 

While the deal centered on Durbin for Harrison, several other pieces were involved. Boston received Durbin, utility men Andruw Monasterio and Anthony Seigler, and a competitive balance pick in the 2025 MLB Draft, which was used on right-handed pitching prospect Marcus Phillips. Milwaukee received Harrison, utility man David Hamilton, and left-handed pitcher Shane Drohan. 

It was an up-and-down first season in a Red Sox uniform for Durbin. When he joined the Red Sox organization, the team wanted the 26-year-old to buy into their hitting philosophy of pulling the ball in the air to better utilize the Green Monster. However, those changes didn't click for Durbin, and he started the year as one of baseball's worst hitters, hitting just .183/.250/.280/.530 in his first 52 games. During that stretch, the 26-year-old ranked among the bottom five of 160 qualified hitters in baseball in batting average (158th), on-base percentage (160th), slugging percentage (157th), OPS (159th), and weighted runs created plus (46, 159th).

However, after working with a local outside hitting instructor, Durbin was able to get back to his 2025 approach, spraying the ball to all fields. From June 1 to Aug. 18, Durbin hit .309/.381/.496/.876, helping power the Red Sox offense to the 32-5 stretch that propelled them into the postseason.

However, as the season wore on, Durbin began to feel the effects of a recurring left pinky injury. In the final 34 games of the regular season, Durbin hit just .213/.346/.269/.615 with only four extra-base hits.

Overall, Durbin posted a solid sophomore season, hitting .248/.332/.378/.710 with 25 doubles, 13 home runs, and 64 runs driven in over 153 games. In addition to the solid, albeit up-and-down season at the plate, Durbin provided elite defense at third base, ranking in the top five in baseball in defensive runs saved (13, 2nd), outs above average (7, 3rd), and fielding run value (6, 3rd), leading all American League third basemen in all three categories en route to a Gold Glove nomination. 

The 29-year-old utility man appeared in 107 games in his first season in a Red Sox uniform, serving as the starting shortstop in the absence of Trevor Story. Monasterio caught fire at the plate, hitting .291/.350/.497/.847 with five home runs, 17 doubles, and 22 RBI in 57 games from May 10 to Aug. 8. 

However, he significantly cooled off in the waning weeks of the season, hitting just .140/.204/.161/.365 in his final 31 games, while seeing his playing time diminish, thanks to the emergence of Nick Sogard at second base and Story's return. 

Overall, Monasterio hit .233/.295/.371/.665 in a super utility role for the Red Sox. 

One of the faces of the Red Sox' 32-5 season-saving stretch, Seigler's energy and passion provided a massive spark for Boston in three different stints with the major league team. The 27-year-old's biggest impact at the big-league level came after his second call-up on June 20, when he hit .271/.330/.448/.778 from June 20 to July 24. 

However, his play began to dip in August as he hit just .204/.322/.306/.628 in 20 games from July 25 to Aug. 30 when he was optioned back to Triple-A to make room on the active roster for the return of injured outfielder Roman Anthony. 

Seigler returned to the big-league roster on Sept. 11, when the team placed outfielder Eli White on the injured list with a torn ligament in his right foot. However, Seigler's return to Boston was brief: he appeared in only one game before landing on the injured list himself with right wrist inflammation that ended his season. 

Overall, Seigler hit .247/.327/.400/.727 with three home runs, 12 doubles, driving in 13 runs in 49 games with the Red Sox. 

With the 33rd overall pick in the 2025 MLB Draft, the Red Sox selected right-hander Marcus Phillips out of the University of Tennessee. The 22-year-old had a rough first professional season with High-A Greenville. In 19 appearances (18 starts), Phillips posted a 6.71 ERA over 61.2 innings with opponents hitting .260 against him. Phillips struggled mightily with command, walking 17.5 percent of batters faced. Those command issues kept hitters from chasing pitches out of the zone, resulting in a 22.5 percent chase rate, which ranked in the 9th percentile among High-A pitchers. 

Phillips' season came to an early end when he landed on the injured list on Aug. 20 after his final start with a trainer. SoxProspects.com currently ranks him as the No. 15 prospect in the Red Sox system. 

The centerpiece of the trade that sent Rafael Devers to San Francisco in June 2025, the 25-year-old spent much of his time in the Red Sox organization in Triple-A with the Worcester Red Sox and made only three appearances for Boston. In those three appearances, Harrison allowed four earned runs on 12 hits across 12 innings, striking out 5 and walking one.

While Durbin struggled to start the season, Harrison excelled in Milwaukee. Through his first 10 starts, the left-hander appeared to be one of the sport's best young arms, posting a 1.57 ERA, the fourth-lowest among starters with at least 50 innings pitched through the end of May. 

However, Harrison's performance began to wane in the final months of the season, as he posted an 8.67 ERA over his last 10 appearances and was shifted to a bullpen role amid his struggles. 

Overall, the 25-year-old left-hander posted a 4.20 ERA in 28 regular-season appearances. Despite being on the postseason roster in both the NLCS and NLDS, Harrison has not appeared in a playoff game. 

Initially an eighth-round selection of Milwaukee in the 2019 MLB Draft, the utility infielder was traded to Boston in December 2021 alongside prospect Alex Binelas and center fielder Jackie Bradley Jr. in exchange for outfielder Hunter Renfroe. After making his major league debut in June 2023, Hamilton appeared in 204 games for the Red Sox across three seasons, hitting .222/.283/.359/.642.

The 29-year-old utility man appeared in 121 games for Milwaukee in the regular season, hitting .245/.314/.336/.650. He's performed well in limited postseason appearances for the Brewers serving as a pinch-runner off the bench. In four postseason games, Hamilton is hitting .455/.500/.727/1.227 with a key solo home run in the team's pennant clinching win over the Los Angeles Dodgers. 

Drohan was initially selected by the Red Sox in the fifth round of the 2020 MLB Draft. The left-handed pitcher spent the first four seasons of his professional career in the Red Sox organization before being selected by the White Sox in the 2023 Rule 5 Draft. After injuries kept him from playing for Chicago, Drohan was returned to Boston.

After being sent to Milwaukee, the 29-year-old began the season in Triple-A; however, the Brewers quickly promoted him to the majors for his debut on April 8. In 33 regular-season appearances for the Brewers, Drohan posted a 4.19 ERA. In his lone postseason appearance, Drohan allowed one run in one inning, walking two and striking out one. 

With Durbin and Harrison at 26 and 25, respectively, there is still plenty of time for things to change; however, the early edge goes to Milwaukee. Harrison, Drohan, and Hamilton combined for 4.1 fWAR in 2026, compared to the 2.9 fWAR the Red Sox received from Durbin, Seigler, and Monasterio. While Phillips certainly adds value and helps even things out, it's hard to assess how much impact he'll have after his rough first season in the Boston system. 

Regardless of where things stand at the end of 2026, this deal will be a fun one to follow as Durbin and Harrison continue their careers.