Answers To 5 Big Questions For Red Sox

On Wednesday, Yahoo Sports’ Jake Mintz published a piece entitled “5 big questions for the Red Sox: Can they re-sign Alex Bregman? How much are they willing to spend?”

Topics included within Mintz’s questions were the likelihood of Alex Bregman returning to Boston, Boston’s backup plan if they are unable to sign Bregman, how to deal with their logjam in the outfield, whether or not they’ve done enough to shore up their starting rotation behind Garrett Crochet, and how much are they actually willing to spend this offseason.

All of these are completely valid questions, and are topics we have covered extensively here at Roundtable.

Let’s dive in one by one, shall we?

I’ll ask each question exactly the same way Mintz did, so we’re all on the same page.

1. “Alex Bregman?”

First of all - Mintz is correct, that’s not a grammatically correct sentence.

Regardless, he brings up a good question:

“Alex Bregman???”

We all know the story at this point - big free agent signing during spring training, was the reason Rafael Devers was asked to change positions, Devers’ pushback eventually led to him being dealt to the Giants, Bregman emerged as the unquestioned leader of the clubhouse, and despite missing a chunk of the season due to a quad injury was still among the best hitters in baseball at his position and was able to help deliver Boston’s first postseason berth since 2021. With all of that said, he still decided to opt out after his first season of a three-year deal, leaving $80 million on the table in search of a contract that will carry him to the end of his career.

While Boston has routinely been reported as being in the pole position for Bregman all hot stove season, recent rumors from prominent baseball podcaster Jared Carrabis have now raised doubt around the idea of the two-time World Series champion returning to the Red Sox to chase his third career ring.

“I don’t feel super great about Bregman coming back, but these things are always subject to change,” he wrote on X on Tuesday. “Bogaerts was pretty much a done deal to return until the Padres swooped in with a crazy offer. These situations are fluid. But, yeah. Doesn’t sound promising at the moment.”

Despite these whispers being floated by Carrabis, my gut tells me Bregman is back in Boston for 2026. With the team loudly swinging and missing on the likes of both Pete Alonso and Kyle Schwarber, there’s plenty of money to go around still. And if Boston shows up to Opening Day 2026 with Roman Anthony and Garrett Crochet as the only names worthy of the marquee, there might be paper bags over the heads of fans in the stands at Fenway Park.

I wish that was hyperbole - Red Sox fans are nuts.

They cannot miss here on Bregman. If they need to overpay, so be it. That’s how this whole thing works.

More on the spending in a bit.

2. “If they don’t get Bregman, then what?”

As I just talked about above - if they don’t get Bregman and they don’t get anyone else, there will be a fan revolt.

But, for the purposes of this exercise and keeping the peace this holiday season, let’s say they have other plans in mind outside of Bregman.

In my personal opinion, the only way to add talent on the level of a Bregman-type, at this point, is through the trade market.

(because we all know they’re not going to pay for Kyle Tucker, so let’s operate as if he’s off the table)

As the days go by, there’s seemingly more and more smoke around Boston emerging as the front runner for Ketel Marte with the Diamondbacks. Alex Speier of The Boston Globe wrote a long piece on Saturday talking about the merits of potentially moving Marcelo Mayer for Marte, and Mark Feinsand of MLB.com took to MLB Network on Tuesday to talk about why the Red Sox are the leaders in the clubhouse on the Marte market.

Those types of reports trickling out over the course of four days tell you something is cooking there.

It goes without saying that Marte is one of the best second basemen in all of baseball, slashing .283/.376/.517 with an .893 OPS, 28 home runs, 72 RBI, and 87 runs scored over 126 games in 2025, earning a Silver Slugger and his third career All-Star nod thanks to his all-around bat.

It might take moving either Payton Tolle or Connelly Early to get the deal done, but sometimes you have to give up talent to get talent.

Marte is now No. 1 on my list of guys I want Boston to bring in, and I have him in that spot instead of Bregman because to me, his return should be a foregone conclusion.

Sign Bregman, trade for Marte, and this team will be right back in the mix in 2026.

If Marte doesn’t work out, there’s still some talent lingering on the free agent market. A big power bat in Eugenio Suarez remains available, having just hit 49 bombs in 2025 for the Mariners and Diamondbacks. That’s production this lineup could desperately use after flaming out in the Bronx in early October. There’s also Kazuma Okamoto and Munetaka Murakami still lingering from Japan - both players have been connected to Boston, with both offering a ton of upside offensively.

3. "How do they simplify the outfield mix?”

Easy answer?

Trade Jarren Duran.

Despite reports that the Red Sox have been overvaluing Duran this offseason on the trade market, he’s quite obviously the odd man out in a group that includes two Gold Glove winners in Ceddanne Rafaela and Wilyer Abreu to go along with Rookie of the Year finalist Roman Anthony.

There’s been rumors for weeks that the Royals are interested in trading for Duran, which should entice Boston as Kansas City has assets that would help the Red Sox in 2026. But as the days move along and no trade goes down between the two sides, you have to wonder what else might be at play.

Breslow is reportedly comfortable moving forward with all four of his top outfielders on the roster heading into spring training. And while that might just be lip service, it could signal that the Red Sox placing a high price tag on Duran has changed their appetite for wanting to move him. If they’re not getting the bites at the apple they want, they’re content rolling with Duran as a fourth outfielder.

Whether or not Duran is content with that designation is a larger conversation we should wait to have until it’s clear that he’s back in the fold for next season.

MORE RED SOX STORIES:

Payton Tolle vs. Connelly Early: Who Should The Red Sox Trade?

Fenway Sports Group Reportedly Selling NHL Team For Over $1 Billion

Veteran Insider Says Red Sox Leader to Land Ketel Marte

4. “Have they done enough to solidify the rotation?”

Annoying answer?

Maybe.

I think the additions of Sonny Gray and Johan Oviedo, both via trade, should be seen through no other lens other than positive. I don’t feel like the price for either player was outlandish, even if the upside is there for guys like Jhostynxon Garcia and Brandon Clarke - both moved in each respective deal.

Gray is coming off a four-year run of pitching some of the best baseball of his career between his time in Minnesota and St. Louis, and Oviedo has flashed at times while pitching for one of the worst teams in baseball over his last three professional seasons (he missed all of 2024 as he recovered from Tommy John surgery).

If both Gray and Oviedo can pitch at their peaks in 2026, they’ll be solid No. 2s and No. 3s behind Crochet. Add in whatever uptick you’re hoping to get from Brayan Bello during his age 27 season on top of either Tolle or Early grabbing that fifth spot and running with it, and there’s enough there to get excited about the starting rotation.

Reports from late November said the Red Sox were done investing in the starting pitching market after the acquisition of Gray. If that’s actually true, it’s truly not the end of the world.

With that said, there are still arms available that could help Boston feel even more confident in their rotation next season than they are now. Guys like Framber Valdez and Michael King are out there, and both would compete for either that No. 2 or 3 role upon arrival. Being able to bump Oviedo and Bello into the 4-5 spots in the pitching rotation would have both fans and media feeling a whole lot better about Boston’s arms moving forward.

5. “How much are they willing to spend?”

Unless you’ve been living under a rock, you know the answer in recent years has been somewhere between “almost nothing” and “not enough.”

And while last offseason was splashy, it was a bit of fool’s gold from a financial perspective.

They brought in Bregman on a big contract that allowed him to opt out immediately, signed Aroldis Chapman to an extremely team-friendly deal after a down stint in Pittsburgh, and traded for Crochet while still on a short money deal before giving him the extension.

Since winning the World Series in 2018, staying under the luxury tax has been the name of the game. And as of December 2025, that mantra remains true.

MassLive’s Sean McAdam reported in late November that ownership is concerned about exceeding the $244 million Competitive Balance Tax threshold in 2026, as this could trigger financial penalties and other operational restrictions.

According to the report, team officials believe crossing that line would result in a “moderate financial loss.” Because MLB teams do not share their financial records, it’s impossible to verify whether that claim reflects actual revenue projections or an internal preference for maintaining a certain level of spending discipline.

Anyone with a brain can tell you that it’s almost certainly the latter.

When the reports came down of Boston’s offer to Alonso only being for three years at $85 million, it was all the confirmation needed to show what McAdam was hearing about FSG was true.

They’re either going to have to get really creative like they did ahead of the 2025 season, or they’re going to have to have a real change in character in the next few weeks if this team is to get any better here before spring training.

If money isn’t an issue (it never should be), this team should be re-signing Bregman, trading for Marte (who plays on a team-friendly deal), signing either Valdez or King (or both), and filling in the gaps where needed.

Realistically? I believe one of the above is going to happen - most likely a Bregman deal, but I’m not holding my breath for any of those four in particular.

In a post-Dombrowski world for the Red Sox, it has become “Death, Taxes and the Red Sox being disappointing every offseason.”

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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.