A $208 million payroll was supposed to help the Boston Red Sox compete with the American League’s best. But it has left them searching for answers after a humiliating postseason exit. Finishing third in the division before suffering a 0-2 sweep at the hands of their archrivals, the New York Yankees, exposed a glaring weakness in Boston’s lineup. Ranking 26th in home runs and 20th in slugging percentage, the Red Sox’s offensive struggles have made one thing clear: keeping the same lineup is no longer an option.

Now, an offseason shake-up could put two familiar faces in the firing line. With an outfield crowded with options and the front office under pressure to turn things around, Jarren Duran and Masataka Yoshida could emerge as potential trade candidates. Both bring intriguing offensive upside, but Boston’s need for a more balanced and productive roster could force some difficult decisions.

“The Red Sox are open to moving one or both of Jarren Duran and Masataka Yoshida this offseason,” Baseball Is Dead host Tyler Milliken quoted Boston Globe’s Alex Speier.

Both Duran and Yoshida saw production collapse in 2026. It complicated their roles in Boston’s future lineup. Duran hit a mere .207 over 151 games. This was a steep decline from his .256 average in 2025 and dragged his career average down to .254.

He became highly susceptible to swing-and-miss stuff, racking up 165 strikeouts in 551 at-bats (608 plate appearances). His total line finished at .207/.266/.361 with an underwhelming .627 OPS. According to advanced analytics tracked on StatMuse, his weighted runs created plus (wRC+) sat at an abysmal 69. That’s around 31% below league average.

Yoshida’s injury history worsened: 87 games in 2026 after just 55 in 2025, with only 5 home runs. Thus, he failed to provide the run production expected from his $18.6 million annual salary.

Younger talent (Anthony, Rafaela, Abreu) has crowded the roster, leaving no everyday roles for Duran or Yoshida.

Financial factors also come into play. Yoshida enters the final season of his five-year, $90 million contract (owed $18.6 million for 2027). It makes a salary dump more realistic than in past winters. Duran has two years of arbitration eligibility left before hitting free agency in 2029. It offers a team control that could still entice trade partners looking to buy low.

In exchange for these two, the Red Sox may be planning to rectify their weak areas.

The Red Sox have diverse areas to rectify ahead of 2027

“I think we’ll look to build pitching depth,” Red Sox CBO Craig Breslow said. “You never have too much of that, whether that is being able to develop an impact on our own major league team, whether it’s to acquire it and then use it to address other holes in the roster that surface down the road. … So while we sit here today and say that we feel good about our rotation and bringing back our entire bullpen, having flexibility and optionable pitching depth is incredibly valuable. We’ll certainly be on the lookout for ways to improve there.”

Sonny Gray hits free agency after declining his $30 million mutual option for 2027. He was Boston’s most dependable starter in 2026, turning in an outstanding 18–5 record with a 2.72 ERA over 169 innings. So, his exit leaves the team without a clear, proven ace to head the 2027 staff.

Moreover, Garrett Crochet missed nearly the entire 2026 regular season. He managed only six starts before returning to throw out of the bullpen in the playoffs. Additionally, right-hander Tanner Houck is still working his way back from Tommy John surgery. Hence, the team is left thin on guaranteed health.

A few new arms could ensure the Red Sox’s pitching depth, and nothing better than trading their surplus outfielders to make space for the new starters.