In June, the Boston Red Sox shocked Major League Baseball by trading their homegrown star, three-time All-Star Rafael Devers, and his massive 10-year, $313.5 million contract to the San Francisco Giants in exchange for two marginal pitchers and a pair of minor league prospects.
Now, according to a mock trade proposal from Daniel Feininger of BoSox Injection, the two teams could link up again this offseason for another blockbuster — one that might yield a more substantial return for Boston.
Chief baseball officer Craig Breslow has made it clear that his offseason priority is to find a dependable No. 2 starter behind ace Garrett Crochet.
Crochet was the only Boston pitcher to exceed 30 starts in 2025 — or even 28, for that matter. Beyond Crochet’s impressive 2.59 ERA (third-best in the American League), the next-lowest ERA among Red Sox starters belonged to Brayan Bello, who posted a 3.35 mark across 166 2/3 innings.
Meanwhile, the Giants are in dire need of offensive help in the outfield. Center fielder Jung Hoo Lee was their top-performing outfielder this year, but his .735 OPS highlights the lack of production from that group.
The Red Sox, on the other hand, have several tradeable outfielders, and none has been mentioned more than 29-year-old Jarren Duran. Duran hit .774 OPS with 16 home runs and an AL-best 13 triples this season.
Duran’s salary is set to jump from $3.75 million in 2025 to a possible $8 million via club option next year, yet he’d still represent an affordable offensive boost for San Francisco — if they were open to dealing right-hander Logan Webb, whom Feininger identified as Boston’s ideal target.
“With the Giants potentially leaning toward a rebuild after selling at the deadline — and with Devers’ massive contract now on the books — shedding Webb’s salary, which sits around $23 million annually through 2028, could make sense if they can get young, cost-controlled talent in return,” Feininger suggested.
While Duran would satisfy San Francisco’s outfield need, the Giants, who were 10 games over .500 and just two games back in the NL West when they acquired Devers before collapsing to an 81–81 finish, must upgrade their lineup to contend again in 2026.
For Boston, Webb would instantly become the most dependable arm available on the market. However, landing him would likely require including one of their top pitching prospects — such as 2025 first-round pick Kyson Witherspoon or left-handed power pitcher Payton Tolle — along with Duran.
Webb has been one of baseball’s most durable starters in recent years, leading the majors in innings pitched this season with 207, just ahead of Crochet. He also topped MLB with 216 innings in 2023 and led the NL with 204 2/3 in 2024. His 3.22 ERA this year trailed only Crochet among Red Sox pitchers, and his 34 starts were the most in the league.
A Duran-for-Webb trade would make sense for both sides on paper — Boston would get the rotation upgrade it needs, and San Francisco would bolster its outfield — but the real question for Breslow is whether parting with both Duran and a top prospect would be a price too steep to pay.
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