Red Sox Linked to Four Free Agent Superstars in 2025

The Boston Red Sox are at another big crossroads with their roster. Last offseason, they showed they can still attract elite talent to Fenway Park by signing Alex Bregman and trading for Garrett Crochet.

Bregman and Crochet have both made strong first impressions in Boston. Their impact has energized fans who are desperate for a return to postseason baseball.

With a loaded free-agent market on the horizon, the team faces some tough choices. The biggest question? Whether Bregman will use his expected opt-out clause.

MLB insider Jon Heyman says Boston could chase several big names this winter. Those moves might reshape the Red Sox for years.

Boston’s Building Blocks: Bregman and Crochet’s Impact

Adding Bregman and Crochet last year marked a real shift in Boston’s thinking. After years of getting slammed for playing it safe, the Red Sox finally spent big and traded for proven stars.

Bregman has anchored the lineup, bringing leadership and power. Crochet has turned into a frontline arm with strikeout stuff that works anywhere.

Now that both are thriving, Bregman’s future becomes a huge concern. His contract includes an opt-out, and given his production, he’ll probably use it.

This decision could completely change how Boston spends and who they target in the 2024-25 offseason.

MLB Insider Links Boston to Five Free-Agent Stars

Heyman’s recent Top 25 MLB Free Agents list ties Boston to several big names. The front office might not land any of them, but the list gives a sense of where they could spend.

Potential Targets for the Red Sox

Here are the main names Heyman linked to Boston:

• Kyle Tucker – The Cubs outfielder is a dynamic offensive threat. Tucker’s lefty swing and speed sound like a Fenway dream, but he’ll likely cost well over $200 million.
• Bo Bichette – Toronto’s shortstop offers great contact skills and can play multiple positions. With Trevor Story a question mark and Marcelo Mayer still developing, Bichette could fill a real need in the infield.
• Kyle Schwarber – He made an impact in Boston during the 2021 playoff run. Schwarber brings power and playoff experience, but the Phillies seem determined to keep him.
• Pete Alonso – The Mets’ slugger is among the league’s best home run hitters. His power would play perfectly at Fenway, but he’ll demand a huge contract and spark a bidding war.

Bo Bichette: The Most Intriguing Fit

Of all the options, Bo Bichette might be the most logical target. With Story’s health still up in the air and Mayer’s timeline unclear, Bichette brings flexibility to steady the infield—maybe for years, or at least until Mayer is ready.

The Infield Equation

Bichette’s steady bat and ability to play multiple positions make him especially valuable right now. If Mayer takes longer to develop, Bichette can hold down shortstop. If Mayer arrives quickly, Bichette could move to second or third, keeping his bat in the lineup.

The Bregman Decision Looms Large

Boston’s whole free agency plan hinges on what Alex Bregman does. If he opts out, the Red Sox might go all-in to keep him or shift to a bigger roster overhaul.

If Bregman leaves, the team would suddenly have payroll space to chase several top free agents. If he stays, Chaim Bloom and company might target just one or two needs—maybe a middle infielder like Bichette or a big bat like Alonso—instead of going wild on spending.

Final Thought: A Pivotal Offseason for the Red Sox

The 2024-25 offseason gives the Boston Red Sox a mix of opportunity and risk. Their shot at contending in the AL East depends on more than just keeping their best players.

They need to add the right piece—or maybe a few—to round out the roster. Should they double down on proven talent like Kyle Tucker?

Or maybe go for versatility with Bo Bichette, gamble on some playoff magic with Kyle Schwarber, or swing for a big bat like Pete Alonso? Whatever they decide, these moves will shape the team’s direction for years.

With stars in their prime, a fired-up fan base, and some payroll flexibility, the Red Sox have a real chance to shake things up. Now, it’s really on the front office—will they play it safe, or take a big swing when the market opens?

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