Sam Kennedy’s pitch to Dustin Pedroia just got rejected again. The Boston Red Sox are desperate to fix their broken team, but they just hit a brick wall. Pedroia is a Red Sox legend. He won two World Series rings, four All-Star spots, an MVP award, and four Gold Gloves. With the team struggling to score runs, bringing back a tough player with a career .299 batting average makes a lot of sense.

However, Pedroia’s refusal only shows the current mess inside the organization. It also adds more questions about Chief Baseball Officer Craig Breslow and his job security. During his appearance on WEEI’s Greg Hill Show, Kennedy gave an update on his efforts to offer the franchise icon a front office role.

“I have over the years,” said Red Sox president Sam Kennedy. “I would love to have Pedey a part of the organization. Unfortunately, the answer I get is a consistent no. He’s very, very happy coaching his kids.”

Since officially retiring, Pedroia has chosen to stay in Arizona to be a full-time dad. He has three sons who all play baseball, and he spends his time coaching their teams. According to Red Sox President Sam Kennedy, whenever the team reaches out to offer him a job, Pedroia turns it down because he is “very, very happy coaching his kids.”

Kennedy hopes to bring Pedroia back from Arizona one day. For now, Pedroia does not want a front-office job. This is nothing new. Pedroia has rejected the team’s offers for the last six years to focus on his family.

This rejection hurts because Boston could really use a leader like him right now. During his 14-year career, Pedroia was the heart and soul of the Red Sox. For example, in 2016, he sparked the team with two huge grand slams, including one in September that snapped a team slump and secured a playoff spot. The front office probably wanted Pedroia to bring that same winning attitude to the 2026 team.

The team this year is going through a nightmare. After an extremely disappointing 10-17 start, Boston fired manager Alex Cora and five coaches. They placed Chad Tracy as an interim manager. However, nothing much improved. The team is still at the bottom in the AL East with a 27-39 record and ranked 29th in terms of scoring runs (258). Injuries are mounting, and the offensive struggle is taking the team far from a Wild Card race.

With Kennedy hard-pitching for Pedroia, speculations around Craig Breslow‘s future are getting raised.

“It’s nearly impossible to imagine Breslow remaining with the Sox past the end of the regular season,” Gordo quoted Sean McAdam.

While Kennedy called the season “embarrassing, unacceptable, maddening, and frustrating,” he confirmed that any decision around Breslow is “not even on the table.” However, the team has a history of firing leaders for building bad rosters, as they did with Chaim Bloom

To make matters worse, Breslow was hired in late 2023 to fix the team after they missed the playoffs. Instead, the team has only gotten worse.

Before firing Cora, there were no rumors or discussions. And for Breslow, the Red Sox have a few more reasons to be upset about.

Red Sox’s rough offseason could also go against Breslow

Apart from not being able to lift the team, Breslow could be targeted for his botched offseason. For instance, with names like Pete Alonso, Kyle Tucker, Bo Bichette, and Cody Bellinger on the free-agent market, the Red Sox failed to sign any of them. Instead, Breslow signed a six-year, $55 million extension with Brayan Bello. He recently got demoted owing to struggles on the mound.

The Red Sox even signed an eight-year, $60 million extension with Kristian Campbell that backfired when the prospect struggled and was demoted to Triple-A. And lastly, Breslow’s misjudgement between Rafael Devers and Alex Bregman cost the team huge.

Breslow frustrated Devers by failing to be transparent during free-agency pursuits that would impact Devers’ position at third base. During the mess, the team traded Devers away. Fans heavily criticized the move because the front office chose its own plans over keeping a star player happy.

However, despite placing Bregman at the hot corner, Boston initially lowballed Bregman. They only offered a three-year deal, frustrating the veteran. He signed the short-term deal but included an opt-out. He utilized that to leave for a five-year, $175 million contract with the Chicago Cubs. In the middle of the chaos, Kennedy’s offer of any front office role to Pedroia serves as a warning to the current CBO.