Alex Bregman signs with Cubs: What’s next for a Red Sox team that hasn’t spent in free agency? taken at BSJ Headquarters (Red Sox)

Troy Taormina-Imagn Images

Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) walks on the field before the second inning against the Houston Astros at Daikin Park.

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

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