The Red Sox Need Sam Kennedy to Stop Talking

As pitchers and catchers report to Fort Myers and optimism traditionally fills the Florida air, the Boston Red Sox should be selling hope, not revisiting old talking points.

Instead, the organization once again finds itself managing headlines generated not by roster moves or on field performance, but by its own front office commentary.

This time, the spotlight falls on team president and CEO Sam Kennedy.

Spring training press availability is routine.

Public relations engagement is part of the job.

Transparency, in theory, is preferable to silence.

But there is a fine line between communicating and complicating.

And in recent years, the Red Sox brass have shown a tendency to step directly into avoidable controversy.

The Bregman Comment That Didn’t Need to Happen

At the center of the latest stir is Kennedy’s remark regarding Alex Bregman’s free agency.

“If Alex Bregman wanted to be here, ultimately he’d be here,” Kennedy stated.

The comment landed awkwardly, not because fans were demanding a full postmortem on the negotiation, but because it contradicted his own words from September.

Back then, Kennedy had said, “That’ll all take care of itself. He wants to be here, we want him to be here, and I’ll leave it at that.”

In September, before opt outs and formal free agency unfolded, it was reasonable not to forecast the future.

Front offices rarely reveal strategy months in advance.

Even a simple “we’re focused on finishing the season” would have sufficed.

Instead, expectations were subtly shaped.

Fast forward to February, and the tone shifted entirely.

Rather than acknowledging the complexities of negotiation, market forces, and contract structure, the comment reduced the situation to a question of desire.

That framing oversimplifies reality.

The Financial Reality

Ultimately, Bregman signed with the Chicago Cubs for five years and 175 million dollars.

Reports suggest Boston’s offer topped out around five years and 165 million.

Chicago included a no trade clause.

Boston, reportedly, did not.

Ten million dollars over five years may not seem monumental in modern MLB economics.

But contract protections matter.

Geography matters.

Organizational direction matters.

Spring training location even matters to some degree.

The Cubs train in Arizona.

Boston trains in Florida.

Players spend much of the year on the road.

Every lifestyle factor weighs into decisions.

None of that reduces to “he didn’t want to be here.”

It reduces to negotiation dynamics and valuation thresholds.

Importantly, skepticism about re signing Bregman long term was not unreasonable.

The 2025 season once again presented flashes of excellence mixed with injury concerns and inconsistency.

A five year commitment at top market value carried risk.

That debate is legitimate.

But the issue here is not roster construction.

It is messaging.

A Team Worth Promoting

What makes the situation more perplexing is that Boston actually has reasons for optimism entering 2026.

The front office added starting pitching depth with Gray and Suárez.

The infield received reinforcement through IKF and Durbin.

Willson Contreras was acquired, adding veteran presence and positional flexibility.

Top prospects Roman Anthony and Marcelo Mayer are expected to play prominent roles, and while both have dealt with injuries, the expectation is for meaningful contributions this season.

That is a compelling storyline.

That is the narrative worth amplifying as the team prepares for exhibition games, beginning with Northeastern University before ramping up against major league opponents leading into Opening Day.

Instead, the discourse circles back to what did not happen last fall.

Revisiting Bregman’s departure does little to energize a fan base eager to evaluate the new roster.

If mistakes were made in negotiation strategy, that chapter closed months ago.

Reframing it publicly now only reopens debate.

The Optics Problem

Professional sports organizations operate in an environment where perception often equals reality.

Fans analyze tone as much as transactions.

When comments appear contradictory across seasons, trust erodes.

Kennedy did not need to restate or reinterpret past statements.

He could have simply emphasized forward momentum.

He could have reiterated confidence in the current roster.

He could have spotlighted development plans and competitive goals.

Instead, the remarks created an unnecessary narrative shift.

Boston is entering a season where pitching depth, emerging prospects, and lineup versatility could define its trajectory in the American League.

The focus should be baseball.

Not backtracking.

Not spin.

Not rhetorical reversals.

Spring training is about new beginnings.

It is about possibility.

It is about resetting expectations.

For the Red Sox, the simplest strategic adjustment may not involve the roster at all.

It may involve restraint at the podium.

Let the players speak with performance.

Let the season define itself.

And perhaps most importantly, let the conversation move forward.