Sam Kennedy says Red Sox have ‘blessing from ownership’ to spend big at trade deadline

On Wednesday night at Fenway Park, it was a classic display of the one-step-forward, one-step-backwards Boston Red Sox of the 2020s.

After taking the first two games of their three-game series against the Cincinnati Reds (45-42) - having won three of their last four games after a six-game losing streak - the Red Sox were up 3-0 heading into the top of the 7th inning with Greg Weissert (3.46 ERA) on the mound.

After Weissert allowed a single to the first batter of the inning, Red outfielder Rece Hinds hit a groundball to third on what should have been a double play ball for infielder Abraham Toro. Instead, Toro misplayed the ball, everyone was safe, and one batter later the bases were loaded with nobody out.

Six pitches later, Reds first baseman Christian Encarnacion-Strand got a hold of a 95 mile per hour four-seamer up in the zone, and Cincinnati was up 4-3 with no outs in the top of the 7th inning. Four batters later, Reds shortstop Elly De La Cruz’s RBI-single made it a 5-3 game.

Bad base running by Romy Gonzalez put a damper on Boston’s immediate comeback attempt one half-inning later, and an error from Trevor Story in the top of the 8th led to two runs scoring to give Cincinnati what was ultimately an insurmountable 8-4 lead.

Instead of being .500 heading into Fourth of July weekend, sloppy baseball leads to Boston carrying a 43-45 record into their three-game series in the nation’s capital against the Nationals (36-50) starting Friday morning.

Greg Weissert
BOSTON, MA - JULY 2: Relief pitcher Greg Weissert #57 of the Boston Red Sox holds his head in his hands after he was pulled from the game following giving up five runs to the Cincinnati Reds during the seventh inning at Fenway Park on July 2, 2025 in Boston, Massachusetts. Photo credit Winslow Townson/Getty Images

It’s clear to anyone watching this baseball team on a regular basis that a change is needed for them to truly compete for what would be their first postseason appearance since 2021, and Red Sox team president Sam Kennedy told The Greg Hill Show on Thursday that his front office has the green light to make moves midseason to help this team improve.

“As far as getting into the postseason, can our expectations be that you guys have got to be big players come the trade deadline to improve a team that you guys feel like, if you can get into the postseason, you can make some noise?” WEEI’s Jermaine Wiggins asked Kennedy.

“Absolutely,” said Kennedy. “We have the ability to do that in terms of, you know, a blessing from ownership, and fulfilling our goal of becoming a postseason team. That said, we have to start playing better baseball on a more consistent basis.

“I mean, when we're playing sloppy defensively, when we're not running the bases as well, when the bullpen’s struggling, it's really hard to keep up in the American League East. So we've got to play better baseball and prove to ourselves over these next seven series that this is a team that can do what we think we can do.

“I mean, we were very aggressive this offseason. We had what we thought was a really great offseason in terms of the additions and the extensions - with Garrett Crochet and Alex Bregman and Aroldis Chapman. We just - for a lot of reasons, we've been a .500 or below .500 team. That's not what we're looking for here. So to answer your question - yes, we do have the ability to go out and improve the team. But we also have to play better baseball, to put ourselves in a position where the postseason is realistic, and we gotta get going.”

Alex Cora and Sam Kennedy
BOSTON, MASSACHUSETTS - JUNE 27: Alex Cora, left, is seen in the dugout with the Sam Kennedy prior to a game against the Toronto Blue Jays at Fenway Park on June 27, 2025 in Boston, Massachusetts. Photo credit Jaiden Tripi/Getty Images

In quintessential Kennedy fashion, he gave himself the trapdoor by qualifying their trade deadline green light, saying the team needs to play better for them to invest. But make no mistake about it - Kennedy said very plainly that they have a “blessing from ownership” to do what’s necessary to achieve their goal of making the postseason.

So if-and-when this team doesn’t do what’s necessary at the deadline, your inevitable calls of anger to 617-779-7937 will be justified, to a degree.

But remember, he gave himself the out.

“If the team’s under .500 at the deadline, will you add?” WEEI’s Chris Curtis asked in a follow-up.

“It's just hard to say, Chris,” said Kennedy. “At this point, you really - I don't want to pick a lane and then have you, you know, play a sound clip in my face for the next six months. So I don't really have any desire [to say right now].”

“So a couple weeks, [let’s say] a deal is in front of you guys, and it requires spending money and prospects,” WEEI’s Greg Hill began with the hypothetical. “But it requires a commitment cash-wise from the ballclub. John Henry is on board, and you and everybody else is on board with that, with spending that money?”

“Absolutely,” said Kennedy. “If it's a fit that helps us get to where we want to go, absolutely. We have the same mindset right now that we had in November, December, January, February, March, that led us to what we felt was a very productive and aggressive offseason. So full-stop, simple answer. But there is a second part of that answer that we have to be realistic.

“I mean, if we don't go out and do the right things, work and win baseball games over the next couple of weeks, we're not going to be in a great position. So we need to start playing better baseball, get back to .500 and winning series to put ourselves in a position to add to this club at the deadline and go take a run at it. But it's impossible to guarantee anything here on July 3rd, because we just have to go out. We got to play better.”

Marco Sturm and Sam Kennedy
BOSTON, MASSACHUSETTS - JUNE 11: Boston Bruins Head Coach Marco Sturm talks with Boston Red Sox President and CEO Sam Kennedy before a game against the Tampa Bay Rays on June 11, 2025 at Fenway Park in Boston, Massachusetts. Photo credit Maddie Malhotra/Boston Red Sox/Getty Images

Kennedy appears to have put the ball in the clubhouse’s court.

Play better, and we will spend on this team midseason.

And if they do, indeed, play better baseball, let’s hope this means higher caliber additions than James Paxton, Danny Jansen, Lucas Sims and Luis Garcia.

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Featured Image Photo Credit: Winslow Townson/Getty Images