Red Sox CEO addresses team’s ‘brutal and truly sort of unthinkable’ trade deadline reality

The Red Sox are in unfamiliar territory. 

CEO Sam Kennedy said Wednesday that despite high expectations entering the season, selling at the Aug. 3 trade deadline may be a reality if the team doesn’t improve soon. 

“It’s brutal. We have rarely found ourselves in that situation and when you do, like every trade deadline, you have to do what’s in the best interest of the organization,” Kennedy said in an interview with NESN. “Not any one person, not a member of the front office, not a player, not an executive, 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.”

“But it’s brutal and truly sort of unthinkable given the expectations. That’s what’s made these first couple of months so difficult, because we did have high expectations internally and externally,” he added. 

Kennedy’s comments come less than a week after an appearance on “The Greg Hill Show,” where he was realistic about the spot the team was in when it was 27-39.

“But look, let’s be honest, unless things change dramatically, we may have to pivot here from what our initial planning was,” he said at the time. “It just wouldn’t be responsible to do otherwise. But here in mid-June, we need to see what happens over the next couple weeks, and then we’ll reassess.”

The Red Sox made the playoffs in 2025 and entered 2026 with expectations of returning, but their season has been an unmitigated disaster, as they sit at 29-43 after Thursday’s loss to the Blue Jays and last in the American League East. 

The team ranks dead last in the league in runs, 21st in hits while drawing the second-fewest walks. The Red Sox’s .314 on-base percentage also ranks just 21st. 

Caleb Durbin, who hit over .250 with the Brewers in 2025, is hitting under .200. Jarren Duran, who hit .256 last season, is at just .213. Trevor Story continues to be extremely whelming at a near-career-low .206.

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The Red Sox’s pitching hasn’t fared much better, as Brayan Bello was demoted to Triple-A and Garrett Crochet, while injured since April 25, pitched to just a 6.30 ERA when healthy. 

Manager Alex Cora was fired on April 26 after a 10-17 start, but the team has regressed further since, going 19-25. 

The Red Sox entered Thursday 5 1/2 games back of the AL’s third wild-card spot with over half the season to play, but must catch five teams to claim the spot, making selling a real possibility.