Boston Red Sox chief baseball officer Craig Breslow has been busy wheeling and dealing this offseason with the St. Louis Cardinals, completing trades for right-hander Sonny Gray and first baseman Willson Contreras. Could a third time be the charm which lands Boston its replacement for Alex Bregman at third base?

Make no mistake: Boston’s top preference appears to be re-signing Bregman, who earned rave reviews on and off the field in his first season with the Red Sox.

But interest in Bregman is bubbling league-wide, so it’s no guarantee he returns to Boston in 2026.

If that’s the case, here’s a name to consider: Nolan Arenado. So let’s run through the pros and cons of trading for Arenado.

There’s no doubt the 34-year-old Cardinals third baseman is heading into the twilight of his career. He hit a career-low. 237 in 2025. And Arenado’s power numbers (12 home runs, 52 RBIs, .666 OPS) were his worst since his rookie year in 2013, COVID season not withstanding.

In his prime, Arenado was a force, earning six top-10 finishes in MVP voting. The eight-time All-Star has won 10 Gold Glove Awards, six Platinum Glove Awards and five Silver Slugger Awards.

Yes, Arenado has clearly lost a step. But here’s the rub: He has just two years and $42 million remaining on his contract. If Boston is willing to deal with his drop in production, Arenado could be a nice short-term solution with one of the Red Sox’s top prospects (Marcelo Mayer? Franklin Arias?) waiting in the wings.

The Boston Globe’s Tim Healey reported on a possible Red Sox-Cardinals Arenado trade last month. So did The Athletic.

“(Arenado) was linked to the Red Sox last winter, and Boston was one of five teams he was willing to approve for a trade,” The Athletic’s Will Sammon, Ken Rosenthal and Katie Woo reported last month.

Look, it’s clear Breslow likes dealing with St. Louis, whose front office is being run by former Red Sox chief baseball officer Chaim Bloom.

And it’s clear the Red Sox aren’t itching to give out a nine-figure contract to Bregman.

Is Bregman a better bet in terms of production on the field and in the lineup? Absolutely.

But Arenado is a cheaper, short-term option who seemingly aligns with the vision of the Red Sox front office.

The Boston Red Sox have adjusted their roster over the past month and a half, and more moves could be on the way. Through it all, Masataka Yoshida’s role with the club in 2026 hasn’t become any clearer.

Yoshida is a DH, but Boston has multiple players who will be in need of DH starts next season.

With the Red Sox in possession of four starting outfielders, it’s presumed that the DH spot, on many occasions, will be filled by one of those players.

Then there’s the new acquisition of Willson Contreras, who is expected to get some DH reps on days that he’s taking a break from first base, with Triston Casas possibly factoring into the equation as a backup first baseman. And speaking of Casas, he’s another guy who could demand DH starts once he’s healthy and looking like himself again.

Boston’s DH logjam would be a lot simpler of Yoshida wasn’t a productive player. There’d be nothing to miss by keeping him out of the lineup most of the time.

But Yoshida’s final month of the 2025 season saw him perform like one of Boston’s best offensive players, indicating that he’s still very much a productive bat when healthy.

It’s always good to have depth, especially because it helps you guard against inevitable injuries. On the other hand, there’s a fine line between depth and too much of it. People who claim that there’s “no such thing as too much depth” aren’t really factoring in the experience of the players who are getting stale on a bench all season long (while chomping at the bit about how they could and would be playing everyday on another MLB team).

This often does something negative to the psyche of a player, and even to a greater clubhouse depending on how that player deals with the situation.

Yoshida has been nothing but a consummate professional by all accounts. This doesn’t seem to be an issue with him, in the sense that Boston’s clubhouse would be affected.

Still, it’s hard to see how the Red Sox will find enough reps for all of their capable bats in 2026. It’ll be up to Alex Cora to work his magic.

Yoshida’s MLB career, starting in 2023, includes a .282 average, 29 home runs, and 154 RBIs over 303 games. Prior to Boston, Yoshida excelled in Japan’s NPB for seven seasons with the Orix Buffaloes, hitting .327 with 133 home runs. He signed a five-year, $90 million deal with the Red Sox in December 2022, running through 2027, with a 2025 salary of $18.6 million.

The Boston Red Sox have made their big offseason moves via trades, but an insider doesn’t think they should continue that approach.

Boston landed a notable lineup upgrade when acquiring Willson Contreras. The Red Sox also landed starting pitcher Sonny Gray from the St. Louis Cardinals, and The Athletic’s Ken Rosenthal reported that they’ve discussed another deal with the National League club for Brendan Donovan.

However, Rosenthal doesn’t believe Boston will make that third trade with former Red Sox executive Chaim Bloom. The insider explained Tuesday on “Foul Territory” why the Red Sox should set their sights on free agency to target another position player such as Alex Bregman or Bo Bichette.

“You can’t keep trading from your system, and Brendan Donovan would cost more in prospects than Contreras or Gray did,” Rosenthal said. “So I expect — and I’ve written — that their next move should be a big free-agent hitter. Whether it’s Bregman or Bichette, even someone else.”

The Red Sox also sent top prospect Jhostynxon García to the Pittsburgh Pirates to acquire starting pitcher Johan Oviedo. Rosenthal thinks they should avoid moving more young talent and instead tackle the open market for another impact hitter.

“That is the way they should go at this point because, again, they’ve traded enough from their system where they would probably be better suited to make a free-agent signing,” he said.

Red Sox chief baseball officer Craig Breslow called it a “priority” to acquire another big batter, but he wouldn’t limit the search to free agency or another trade.

According to a new report from The Athletic’s Ken Rosenthal and Will Sammon published Monday, the Boston Red Sox have discussed a potential Brendan Donovan trade with the St. Louis Cardinals.

“St. Louis Cardinals president of baseball operations Chaim Bloom, who already has traded right-hander Sonny Gray and first baseman Willson Contreras to the Boston Red Sox, might not be done dealing with his former club,” Rosenthal and Sammon wrote.

“The Cardinals and Red Sox also have discussed a trade that would send infielder/outfielder Brendan Donovan to Boston, according to people briefed on the conversations. Donovan likely would play second base for the Red Sox, who have also been linked to the Arizona Diamondbacks’ Ketel Marte.”

Rosenthal and Sammon clarified that no deal is close.

Donovan’s 2025 season with the Cardinals showcased his versatility and talent despite setbacks. He had a career year, batting .287 over 118 games with 10 home runs, 50 RBIs, and 64 runs scored, while posting a .775 OPS and making his first All-Star team. A left groin strain sidelined him from mid-August, ending his year early as the Cardinals finished 78-84, fourth in the NL Central.

Across his four-year MLB career, all with St. Louis, Donovan has maintained a .282 average, with 40 homers, 202 RBIs, 241 runs, and 498 hits.

The Boston Red Sox might need to find a new answer against left-handed pitching…

The Seattle Mariners came to an agreement with outfielder Rob Refsnyder on a one-year contract on Monday.

This is a breaking news story that will be updated.