Alex Bregman signs with Cubs: What’s next for a Red Sox team that hasn’t spent in free agency?

If you’re a Red Sox fan, you’re probably sick and tired of reading the same story every offseason: Boston didn’t do enough in free agency. This time, it was Alex Bregman. The Red Sox failed to outbid the Cubs, and the All-Star third baseman is headed to Wrigleyville.

Bregman agreed to a five-year, $175-million deal with Chicago that includes no opt-outs, a full no-trade clause, and $70 million in deferred money, according to The Athletic’s Ken Rosenthal.

If your optimism now rests on Bo Bichette being the Red Sox’s fallback plan to improve the roster, brace yourself — he’s going to cost more years and more money than Bregman.

The deal the Cubs gave to Bregman wasn’t something the Red Sox couldn’t do. They simply didn’t want to commit to the player on anything other than their own terms. Boston could have offered the deferrals that Chicago issued in the deal, lowering the AAV (average annual value).

Bregman was the best free agent fit for this team outside of Pete Alonso, who signed with the Orioles at the beginning of the offseason. The veteran is a proven winner, making the postseason in each of his big league seasons and winning two World Series championships, and he instantly changed the dynamic in the Sox’ clubhouse the second he arrived at spring training.

Last February, the Red Sox shocked fans by signing Bregman to a three-year, $120-million deal that included opt-outs that allowed him to dip back into free agency and get one last big payday. The deal had deferrals, and more importantly, he would be mentoring the young clubhouse and an emerging core that featured Roman Anthony, Marcelo Mayer, and Kristian Campbell.

It was the first time in a long time that the Sox made a big splash in free agency. In fact, the Sox were very aggressive last year, trading for Garrett Crochet and signing him to a six-year contract extension. Boston finally started to give the impression they were serious about winning and signaled to the fan base they were ready to take advantage of this window of young talent.

The arrival of Bregman and Crochet led to a playoff berth, ultimately losing in the American League Wild Card round to the Yankees in the Bronx.

As the offseason began to unfold, the Red Sox were rumored to want to add two power bats. They’ve added one in Willson Contreras. They’ve also let viable options in Alonso, Bregman, and Kyle Schwarber sign in other markets.

Boston reportedly didn’t offer anything more than a three-year deal to Alonso. Schwarber wanted to remain in Philadelphia, and it would have taken a massive offer to lure him back to Boston.

The Sox have been linked to Ketel Marte, but the D-backs have reportedly removed him from the trade block. Even if the Sox and D-backs re-engage in trade talks, Arizona knows they have Boston over a barrel, and it’ll cost Breslow a massive trade package.

Marte makes a ton of sense, and Boston fans aren’t going to care what it’ll take to land him at this point. Since 2023, the 11-year veteran has been one of baseball’s most complete offensive players, earning back-to-back All-Star nods in 2024 and 2025 while slashing .283/.376/.517 with 28 home runs last season. His contract—six years, $116.5 million—is widely viewed as team-friendly, especially when stacked against what Bregman could command on the open market. Defensively, Marte remains reliable, ranking in the 74th percentile in range among second basemen.

The attention is now turned to Bichette, but he’s expected to meet with the deep-pocketed Phillies this week. In addition, Philadelphia recently hired Don Mattingly to be its new bench coach. Mattingly and Bichette have a great relationship, serving as a mentor for the former Blue Jays shortstop.

If the Red Sox miss out on Bichette, too, their options dwindle dramatically as to who they could bring in and play third base.

One potential alternative is Eugenio Suárez, who would unquestionably add thump to the middle of the order. Suárez split last season between the Diamondbacks and Mariners, launching 49 home runs with 118 RBIs—tying his career high from 2019.

He’s not the answer, but might be their only option by default.

Offensively, that production plays anywhere. Defensively, it’s another story.

Suárez would represent a significant downgrade from Bregman at third base for a Red Sox team that has already been among the league leaders in errors over the past two seasons. In 2025, Suárez posted -6 Defensive Runs Saved and -3 Outs Above Average, continuing a multi-year trend of average-to-below-average defense.

Boston could stomach defensive limitations if the bat were truly elite and consistent—similar to the calculus with Pete Alonso at first base. But Suárez also comes with swing-and-miss concerns, ranking in the 5th percentile in strikeout rate (29.8%), numbers uncomfortably reminiscent of Bobby Dalbec. Power alone isn’t enough if it further destabilizes an already shaky infield.

Another option: Breslow could give his new best friend, Chaim Bloom, a call and make a third trade with the Cardinals this offseason. Boston has been linked to Brendan Donovan. They were also linked closely to Nolan Arenado last offseason.

It’s hard to believe Arenado’s name hasn’t surfaced in trade discussions between Craig Breslow and Chaim Bloom. His contract, in fact, is relatively workable — especially given how motivated St. Louis appears to be to move it. Arenado is owed $27 million in 2026 (with $5 million already covered by the Rockies) and $15 million in 2027. The Cardinals, firmly in rebuild mode, would gladly shed a significant portion of that salary, while the Red Sox would aim to cap their financial exposure to avoid negative surplus value. Given Bloom’s deep familiarity with Boston’s farm system and the recent trade dialogue between the two organizations, finding common ground would not be difficult.

Arenado has a no-trade clause and desperately wants out of St. Louis as they undergo their rebuild. For Boston, they get another aging veteran with a short-term commitment and likely will get the Cardinals to pay down some of the salary owed to Arenado. They trade changes dramatically if Donovan is added to the mix. If Boston adds Arenado, they can move Mayer to second base and roll with their young core and the Cardinals' veterans from last season.

Boston has the pieces to trade from their farm system. Their pool of young positional players has dwindled, but with Mikey Romero, Franklin Arias, and Henry Godbout as the next wave, they could trade from that pool of players.

For the Cubs, they add a proven winner in Bregman while also enjoying a strong offseason to round out their roster. Chicago has added veterans to beef up its bullpen; they signed first baseman Tyler Austin to a one-year deal. If you recognize his name, that’s because he was the one who fought Joe Kelly a few years back. The Cubs also traded for Marlins right-handed starter Edward Cabrera last week.

Miami received outfield prospect Owen Caissie, along with minor-league infielders Cristian Hernandez and Edgardo De Leon. Caissie is a good player, very similar to Kyle Stowers, who they got in a deal from the Orioles.

The move to bring in Bregman likely signals the end of Kyle Tucker’s time in the Windy City. It also helps the Cubs write a wrong from last season when they were outbid for Bregman.

The gamble Bregman made on signing, essentially, a one-year deal with Boston, parlayed with his new Cubs’ deal, turns out to be a six-year, $215 million deal, which is good eating for a player embarking on the back nine of his career.

Which brings me back to Boston. They traded Rafael Devers in a massive salary dump and received pennies on the dollar in terms of player return. They’ve already traded James Tibbs III one of the players they got back for Devers. Breslow better hope that Kyle Harrison develops into a regular rotation piece, Jordan Hicks can figure it out and become an impact bullpen arm, and Jose Bello, the other young arm, makes any impact at all.

The move to trade Devers was to create financial flexibility, and the Red Sox have yet to show what exactly they have with that extra money. When it comes to John Henry, it’s all about dollars and cents; losing out on Bregman because they didn’t want to get uncomfortable in free agency makes absolutely no sense.

The other unfortunate part of Bregman signing with the Cubs is the timing of the announcement. Just hours earlier, the Red Sox wrapped up Fenway Fest in Boston, where Breslow, manager Alex Cora, and team president Sam Kennedy were once again pressed about the club’s free-agent pursuits — and the continued lack of meaningful spending. It would have been good theater to hear what Breslow, Cora, and Kennedy had to say if the Bregman news had dropped a mere eight to 10 hours earlier in the day. 

As has become routine, Kennedy’s response landed with a thud. He leaned heavily on the familiar talking point that the Red Sox were “very aggressive” last year and already have nearly $500 million committed in contracts. That argument rings hollow. Big-market teams don’t celebrate the opportunity to contend — they invest aggressively to win, year after year. Historically, that’s what Boston did. Lately, it hasn’t been.

“I think it’s just important to look at the facts,” Kennedy said at Fenway Fest on Saturday. “If you go back a year ago, this date last year, I believe our organization has taken on close to $500 million in contractual commitments to guys like Garrett Crochet, guys like Kristian Campbell, guys like Roman Anthony. So that’s just a fact. We’ve added $40 million in payroll through trades. That’s just a fact. We cannot and do not try to control social media narrative. We understand that talk radio is ablaze with opinions and ideas. That’s what makes this the best place in the world to be, to live, and to operate in baseball.”

Since Opening Day last season, Boston signed Crochet to a six-year, $170-million deal; Campbell to an eight-year, $60 million deal; Anthony to an eight-year, $130 million deal; and Aroldis Chapman to a one-year, $13-million deal.

There’s been a growing disconnect coming out of Fenway Park for several seasons now. The messaging doesn’t match the actions, and the fan base—particularly on social media—has grown louder, more frustrated, and more cynical as a result. At some point, that criticism can’t fall solely on the fans. Those with real platforms—the media members who cover the team daily and the personalities with massive reach—need to be willing to call this out for what it is: an organization increasingly unwilling to operate like the Boston Red Sox.

There are valid baseball reasons why the Red Sox could justify not signing Bregman. But free agency is never without risk. Rarely are teams shopping for players in their mid-20s entering their prime; more often, it’s aging veterans chasing one final payday. Bregman will get his in Chicago. Boston chose not to be part of that equation—and is left holding the bag.

And yes, perception can change quickly. If the Red Sox pivot and land impact talent—if spring training opens with a roster featuring names like Contreras, Bichette, Crochet, Sonny Gray, and a promising young core—the narrative flips overnight.

But for now, Red Sox fans are left with more questions than answers, and quite frankly, enough is enough.