Alex Bregman has always been in the limelight since joining the Red Sox, and now he’s making waves again—but for different reasons. His decision to opt out with two years still remaining on his contract has put Boston in an unexpected position. As Craig Breslow reshapes the roster this offseason, one question looms large: Should they re-sign him? The answer seemed obvious until a slugger from Toronto entered the free agency market, and analysts were asking to look in that direction.

A-Breg looked exactly like what Boston needed in the middle of their lineup. He was hitting .299 with a .938 OPS through 51 games, piling up 17 doubles and 11 home runs while driving in 35 runs. Those numbers made him a legitimate force in the lineup.

But after returning from injury, the production dipped noticeably—his average fell to .250 and his OPS dropped to .724 over 63 games. That is not bad, but for the team that needs “impactful middle-of-the-order bats,” as Breslow mentioned, the re-signing decision becomes a little complicated.

Here’s where things get interesting. MLB insider Jon Morosi recently revealed that multiple teams see Bo Bichette as a potential third baseman, not just a shortstop.

He posted on X: “Can confirm Bo Bichette has received interest from multiple teams who view him as a second baseman or third baseman, due to the presence of an established shortstop on those rosters. Further evidence that the World Series augmented his value in the marketplace.”

That opens a door for Boston. Bichette, at 27, brings both youth and leadership—qualities that could energize the clubhouse. His defensive versatility adds another layer of appeal. The financial comparison is striking: while Alex Bregman’s projected long-term deal hovers around five years and $160 million (roughly $30 million annually for a player entering his age-32 season), the Red Sox could pivot to Bichette at a similar cost but with more productive years ahead.

Bichette, who had a .311 batting average, 18 home runs, and 94 RBIs last season, is young, a good leader, and tough, which fits in wonderfully with Breslow’s long-term plans.

The argument is even greater in favor of money. Bichette’s predicted agreement of $186–187 million is similar to what Bregman is slated to receive, but it’s a better deal because Bichette is younger and has more growth potential.

Brian Burrows, a baseball writer, said, “Bregman isn’t going to be cheap — somewhere in the $30 million per year range — and Boston might need to use that money elsewhere to make upgrades.”

For now, Bregman’s return remains uncertain. And with that comes a critical question: Will the Blue Jays let their shortstop go so easily?

But here’s the catch that could derail Boston’s plans entirely.

Boston’s window on Bregman may close if Toronto locks in Bichette

The timing could not be more interesting for the Boston Red Sox, who are itching to lock down their middle-of-the-order solution.

Bob Nightengale, an insider for Major League Baseball, said that the Blue Jays will probably re-sign Bo Bichette this offseason. Nightengale writes, “Bichette, who was expected to depart Toronto a year ago and whose name surfaced a year ago in trade talks, now is expected to stay put to complete their goodwill tour.”

If Bichette stays, Boston’s math gets harder. They’ve already been thinking about whether to bring Alex Bregman back after a season that was hard for him due to injuries and concerns about his age.

However, if Toronto retains its shortstop, the Red Sox will have fewer opportunities to capitalize and will lack leverage in their search for a more affordable and valuable option.

The clock is ticking. Boston is still interested in Bregman, but the Blue Jays’ likely decision to keep Bichette makes it more urgent and competitive.

The Red Sox have to decide not only on Alex Bregman’s health and contract, but also if their competitors will let him go.