Where do Red Sox go from here after Bregman's Cubs deal?

BOSTON -- For the second consecutive winter, Alex Bregman was a hot topic at Fenway Fest without actually being there.

Hours after Saturday’s annual feel-good event was over, it became apparent that the next time Bregman is at Fenway it will be for the final series of the ‘26 regular season when the Red Sox host the Cubs.

That’s right. The Cubs.

Following a daylong event in which chief baseball officer Craig Breslow, manager Alex Cora and several players expressed hope that their leader from last season would opt to return to the Red Sox, Bregman instead agreed on a five-year, $175 million deal with the Cubs, a source told MLB.com’s Mark Feinsand.

The Red Sox, who acquired first baseman Willson Contreras just before Christmas but have been seeking another potent right-handed bat to round out their lineup, will now have to pivot with Bregman off the board.

Infielder Bo Bichette is the best available alternative via free agency, though his market has heated up in recent days, with the Phillies the latest team to express interest.

Could it be that the Red Sox will make a bigger offer to the 27-year-old Bichette than the reported “aggressive offer” they made last week to the 31-year-old Bregman?

Under John Henry’s ownership, Boston has often been reluctant to make big financial commitments to players in their 30s.

Bichette, a shortstop to this point in his career, has expressed a willingness to move to second base. That is where he would fit best in Boston with shortstop Trevor Story under contract with the club for two more years.

With Bregman leaving, that would open up third base for Marcelo Mayer, the No. 4 overall pick in the 2021 Draft who made his debut with the Red Sox last season before suffering a season-ending right wrist injury.

On Saturday, Mayer said he was mentally and physically preparing himself to play either second or third base depending on how the rest of the roster filled out.

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Bichette’s father Dante finished his solid career with the Red Sox in 2000-01. In fact, Bo’s parents met at a Gold’s Gym just behind the Green Monster.

If the Red Sox could land Bichette, he would be able to take aim at that Monster for the next several years.

In 35 career games at Fenway, Bichette has a batting line of .329/.382/.524 with six homers and 30 RBIs.

Another free-agent option is third baseman Eugenio Suárez, who is more of an all-out slugger (.228 average, 49 homers, 118 RBIs last season) than Bregman or Bichette.

It could be that the Red Sox acquire more of a pure hitter than a power bat. Brendan Donovan (Cardinals) and Nico Hoerner (Cubs) are two trade candidates that come to mind. Donovan hits lefty while Hoerner hits from the right side, which would help Boston’s quest to balance out a lineup that already has several strong left-handed bats.

Breslow said Saturday -- prior to the Bregman news -- that free agency was his preferred path to round out the lineup, because he's already made several trades over the last two winters and needs to be mindful of his organizational inventory.

But as is always Breslow’s way, he didn’t rule anything out.

"It's really hard to know how other teams are going to behave. There are still good players on teams that are going to end up getting traded,” Breslow said.

As for Boston’s relationship with Bregman, this ends an odyssey that started last offseason, when the club spent months monitoring his free-agent status and wound up signing him to a three-year, $120 million deal (including deferrals) that included two opt-outs just days before the official start of Spring Training.

After a strong season with the Red Sox, Bregman wasted no time exercising his opt-out in November.

Given that Bregman didn’t have a qualifying offer attached to him this offseason, agent Scott Boras was confident his client could get the long-term deal that proved elusive last winter. The Cubs, who also pursued Bregman last offseason, got their man this time.

The Red Sox had recently made an offer they felt had the potential to close the deal.

“The ball is in his court,” Cora said earlier on Saturday. “Obviously we've been working together to see what happens, but obviously it's a different offseason for Alex.”

After a successful 2025 season in which the club returned to the postseason for the first time since ‘21 but was eliminated by the Yankees in Game 3 of the American League Wild Card Series, Boston’s goal is a deep postseason run. Finding one more bat could be key to making that goal realistic.

“Our fans, in the end, want exactly what we want,” said Red Sox president/CEO Sam Kennedy. “And we have an obligation to give it to them. And that's getting to October and winning in October. No one is popping champagne over getting to a Wild Card Series.”

Cora encouraged fans to be patient.

"The offseason is not over -- from experience," Cora said. "J.D. Martinez walked in a week into camp [in 2018] and he made a big difference. Alex walked in last year the last day before report day, and he made a huge difference. So we'll see what we have in the next few weeks.”

Breslow will be leading the charge in putting the final touches on a talented roster.

“I think, as evidenced by the fact that it's Jan. 10 and there are still a lot of really talented free agents out there, it indicates that the market is moving fairly slowly and deliberately,” Breslow said. “I guess at this point we remain engaged. And like I said and have said all along: We’re going to do everything we can to improve our roster.”