3 Red Sox trade candidates the Brewers should target at the 2026 deadline

The first half of the 2026 season is coming to an end, and that means trade season is upon us. Though the expanded playoffs and a crowded AL Wild Card picture are complicating the situation, most teams should have a pretty good grasp on whether they are going to be buying at the trade deadline, selling, or staying put with the roster that they have built.

The Milwaukee Brewers, by all standards, will be buyers. The Brew Crew not only sits atop the NL Central with a 6.0-game cushion as play begins on July 9, but they also currently hold the second-best record in all of baseball. Pat Murphy's squad looks poised to once again earn a first-round bye in the postseason, just as they did a season ago when they posted the best record in baseball. However, despite their dominance last year, Milwaukee's deadline acquisitions, which included a backup catcher, a outfield depth piece, and an injured reliever, were modest.

This season, however, feels significantly different. Milwaukee has even more assets in their minor league system, with a logjam of guys at multiple positions that the team will have to move at some point. They have the best pitcher in baseball in Jacob Misiorowski leading their rotation, and there's a potential lockout looming that could reshape the game of baseball as we know it. The time to go "all-in" might be now.

Meanwhile, on the flip side of this trade deadline conversation is the Boston Red Sox. Though Boston has improved over the last month, in large part due to a five-game winning streak that they are currently riding, they are still at something of a crossroads, where they need to decide if it's worth keeping their valuable trade assets at the deadline, or if they should add more young talent to their potential-laden roster.

The Brewers and Red Sox have been trade partners several times over the last few years, with players like Travis Shaw, Mauricio Dubon, Hunter Renfroe, Quinn Priester, David Hamilton, and of course Kyle Harrison joining Milwaukee via trades with Boston in recent years. The connection is there, and should Matt Arnold place a call to the 617 area, there are a couple of targets the Brewers should be eyeing up.

The Brewers' top Red Sox trade targets should Boston decide to sell at the deadline

1. SP Sonny Gray

Should Milwaukee not be able to work out a deal for Tarik Skubal, Sonny Gray would be a solid backup option. The 36-year-old former Cy Young runner-up is putting together an impressive season in Boston, with a 10-1 record and a 2.61 ERA to back it up. The veteran right-hander, who has six postseason starts to his name, is exactly the type of complimentary piece that any contending team would love to add to their roster at the deadline.

Unfortunately, there are a few things working against the Brewers' chances of landing the 3x All-Star, who was snubbed from the Midsummer Classic this year. First, included in Gray's contract is a full no-trade clause, meaning the veteran starter has the ability to decline any trade that Boston agrees to with him included. Milwaukee should be an enticing destination for any starting pitcher given the team's excellent pitching department, but it's entirely possible Gray declines a move to The Good Land.

Additionally, while Gray's modest salary of $11 million in 2026, of which about $4 million would remain after the deadline, isn't necessarily a deal breaker for the Brewers, the $10 million buyout of his $30 million mutual option for the 2027 campaign, certainly complicates things. With that money involved, the Brewers would either have to bolster their trade package and have Boston send them some cash, or shoulder the financial burden themselves. A trade for Gray would certainly be uncharacteristic of the Brewers, but it would undoubtedly give them a rotation that could defeat the mighty Los Angeles Dodgers in the postseason.

2. CL Aroldis Chapman

I have to be honest, I NEVER thought I would type the words Aroldis Chapman and Milwaukee Brewers trade target together. Yet, here we are. The flame-throwing lefty, who like Gray, has had more than one stint in the NL Central, would be the best addition that the Brewers could make to their bullpen at the 2026 deadline.

Chapman is having a career renaissance in Boston, earning All-Star honors in each of his two seasons with the Red Sox. The 38-year-old southpaw, who finished 7th in Cy Young voting last year, is currently sporting a 2.36 ERA with 18 saves in 20 opportunities, while compiling 35 strikeouts in 26.2 innings pitched. It's not quite the 1.17 ERA and 0.70 WHIP he posted a season ago, but with his 40th birthday on their near horizon, Chapman remains dominant. There's no denying that adding Chapman to the three-headed monster of Aaron Ashby, Abner Uribe, and Trevor Megill would give the Brewers the best back-end bullpen group in baseball.

However, Chapman, as the top bullpen arm available, is guaranteed to require a significant prospect haul, and for half a season of a relief pitcher, it would certainly be uncharacteristic of the Brewers to part ways with that much talent. Additionally, Chapman would be owed roughly $4.5 million for the final two months of the season and holds a $13 million player option for the 2027 season, assuming he surpasses 40 innings, which looks all but guaranteed. $13 million would be the highest single-season salary the Brewers have ever paid a relief pitcher, but on the flip side, every time Chapman's been traded at the deadline, the acquiring team has gone on to win the World Series.

3. RP Garrett Whitlock

Should Chapman's price tag get out of control, the Brewers could pivot to another Red Sox reliever, who is having just as dominant of a season. 30-year-old Garrett Whitlock appeared as both a starter and reliever for the Red Sox in 2022 and 2023, before Tommy John surgery caused him to miss all but four starts in 2024. However, since the surgery, Whitlock has transformed into one of the most dominant relief pitchers in all of baseball.

Over the last season and a half, Whitlock has appeared in 93 games, posted a 2.29 ERA, a 1.05 WHIP, and collected 125 strikeouts in 102 innings pitched. He's been Chapman's dominant set-up man and could continue in that role with the Brewers, who wouldn't have to change Megill's role as the ninth-inning man.

Additionally, Whitlock brings with him contractual flexibility. The right-hander is pitching on a $7.5 million salary of which about $2.5 million would be owed after the trade deadline, and has club options for the 2027 and 2028 seasons included in his contract. Though the options, which are $8.25 and $10.5 million, respectively, are slightly out of the Brewers' budget when it comes to relief pitchers, a potential salary floor, or changes to the arbitration system could make them look more enticing next year. With an offseason trade of Megill or even Whitlock within the realm of possibilities, having the flexibility baked into the latter's contract would end up being an asset for the Brewers.

There's no guarantee Boston sells at this year's deadline. In fact, entering play on July 9, the Red Sox are just 3.0 games out of a playoff spot in what is a very crowded AL Wild Card picture. Boston has been known to not bow out of seasons if there's even a slight possibility of them qualifying for the postseason, but should the next three weeks not go their way, moving on from their valuable assets would be the wise move. In such a scenario, expect the Brewers to be placing many calls to Craig Breslow and company as the deadline draws nearer.

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