The Boston Red Sox started the year with high hopes. They changed a lot of players over the winter. But now, they are stuck in last place in the AL East. With the trade deadline coming up fast, team president Sam Kennedy faces hard questions.

This is a crucial period for the franchise. If they decide to sell their best players right now, they are sure to miss the playoffs. And that will only make the fanbase angrier. But if they keep their players while losing, they ruin their chance to rebuild for 2027. The choices they make right now will decide if they can save the 2026 season or if they need to build a new winning team for the future.

“You have to do what’s in the best interest of the organization. And that’s what we’ll do if we’re in that position,” the President and CEO of the Red Sox addressed the reality of selling off pieces. “But it’s brutal and truly sort of unthinkable given the expectations.”

Boston has had a brutal season in 2026. Last year, their postseason run ended early with a defeat to the New York Yankees in the Wild Card Series. Fans and the front office thought there would be a change of scenery, given the number of people they brought in this offseason. But despite a few notable upsides, the Red Sox haven’t shown much promise. And they are last in their division with a 29-42 record. 

“You have to do what’s in the best interest of the organization, not any one person, not a member of the front office, not a player, not an executive, not an owner,” Kennedy was straightforward in the NESN interview. 

However, Boston has historically acted as a buyer during the trade window. Last summer, in an attempt to push for the playoffs, chief baseball officer Craig Breslow acquired lefty reliever Steven Matz from the St. Louis Cardinals and RHP Dustin May from the Los Angeles Dodgers just before the 6:00 pm cutoff.

During their last World Series run, the Red Sox brought in starter Nathan Eovaldi and LF Steve Pearce. Both of them were huge help in the postseason, and Pearce even went on to win his first World Series MVP in 2018. 

But it’s different this year. Instead of getting more players, they might sell off a few existing pieces. Analytics views a 2014-style approach as a realistic outcome. That year, the Red Sox went on a fire sale, offloading veterans like Jon Lester and Andrew Miller to kickstart a new chapter. Today’s team has similar players to trade. Pitchers like Aroldis Chapman and Ranger Suárez could bring in great young prospects. This would speed up a new rebuild and help them open a new winning window.

But Sam Kennedy doesn’t believe that the offseason decisions were the root of their disappointment.

Kennedy defends the moves despite brutal results

“The offseason, the guys who’ve come in to the Red Sox organization, Sonny and Ranger and Wilson and Chappy with the extension, I mean, they’ve done their part. They’ve been great,” Kennedy backed the decisions. 

And he isn’t wrong. Sonny Gray has a 3.03 ERA (8-1), and Ranger Suárez, who signed a 5-year, $130 million contract this year, recorded a 3.75 ERA with 70 strikeouts. Aroldis Chapman, in his second year in Boston, is one of the best relievers in the league this season with a 0.44 ERA. He has 14 saves from just 21 games. Willson Contreras is doing well at first base and is tied for 4th in the league with a .940 OPS. 

But they aren’t the only examples of the overhaul. Johan Oviedo is on a 60-day IL after struggling with a 9.82 ERA. Isiah Kiner-Falefa and Caleb Durbin are producing as expected. 

At the same time, Jarren Duran, in his sixth season with Boston, is going through his career-worst numbers. So, the disappointment isn’t only with the recruits.

Now the point remains whether or not they have a choice when the deadline is here.