Alex Bregman’s Free-Agent Priority; Potential Red Sox Risk

The Boston Red Sox face a pivotal offseason decision about star third baseman Alex Bregman. He looks ready to move on from short-term contracts and settle down somewhere for good.

After a strong debut season in Boston, Bregman’s heading into free agency with one thing on his mind: stability. He and his agent, Scott Boras, are reportedly eyeing a six- or seven-year deal, which could spark a bidding war among baseball’s big spenders.

Bregman’s Journey to Boston and Free Agency Plans

Bregman’s time in Boston started with a bit of a gamble. He turned down bigger guaranteed contracts from the Tigers and Cubs, instead taking a high-value “bridge” deal with the Red Sox—one year at $40 million, with player options that could push it to $120 million over three years.

This setup let both sides get to know each other before thinking about something longer term. It wasn’t the safest route, but it gave Bregman room to maneuver.

Lessons Learned from His First Free Agency Experience

Bregman’s first trip through free agency had its bumps. He chose flexibility over security, which gave him freedom but left his long-term future up in the air.

Now, as he opts out of his current deal, he’s looking for a contract that’ll carry him through the rest of his career. He wants stability for himself and his family.

Boston’s Perspective: Familiarity vs. Fierce Competition

Bregman told MassLive he’s enjoyed his time in Boston and is open to talking about a long-term extension. The Red Sox have some advantages here—familiarity, fan support, and a solid season to point to.

But they’re up against serious competition from teams that can offer big, long-term contracts.

Teams in the Hunt

Bregman’s potential suitors range from traditional powerhouses to rising contenders:

• New York Yankees — Always searching for proven postseason talent.
• Philadelphia Phillies — Strong infield, but Bregman could be their missing piece.
• Chicago Cubs — Showed interest before and might circle back.
• Detroit Tigers — Rebuilding with youth, but need veteran leadership.
• Kansas City Royals — Surprise contenders looking for experience at third.
• Seattle Mariners — Playoff hopefuls with some holes to fill.

Why Bregman’s Market Has Grown

This offseason, Bregman’s not tied to a qualifying offer. Teams can sign him without giving up a draft pick, which definitely sweetens the deal for clubs wary of losing future assets.

His postseason resume, steady bat, and clubhouse leadership should draw plenty of long-term offers, even if some teams hesitate because of his age or injury history.

Potential Challenges

Age is going to be a factor—Bregman’s 32, and a lot of teams see that as the start of the decline years. He’s had some soft-tissue injuries in the past, which might make front offices nervous about a six- or seven-year commitment.

Still, if a team wants to win now, Bregman’s proven skills on both sides of the ball might make those risks worth it.

What This Means for the Red Sox

If the Red Sox want to keep Bregman, they’ll have to change their approach. A short deal probably won’t cut it this time.

They need to make a real, long-term offer if they’re serious about keeping him—and honestly, it could send a strong message to the fans and the rest of the league heading into 2025.

Final Thoughts

Alex Bregman’s free agency is shaping up to be one of the defining storylines of the MLB offseason. Whether he stays in Boston or heads somewhere new, he’ll be looking for some real stability this time.

The Red Sox face a tough call. Will they pay what it takes to keep one of their most reliable, battle-tested guys, or just let him walk?

Whatever happens, Bregman’s next contract won’t be cheap. Whoever lands him could see their whole franchise shift in a big way.

 
Here is the source article for this story: What Alex Bregman considers a ‘very high priority’ in free agency, plus one factor that might hurt Red Sox