The Chicago Cubs have some interesting decisions to make when it comes to attacking this upcoming offseason.

While nothing is set in stone right now, the writing seems to be on the wall that Kyle Tucker’s time in Chicago has ended. Multiple reports have come out saying that the Cubs don’t expect to be competitive in his free agency market, given that he’s expected to command around $400 million. That’s twice as much as what the Cubs have ever given a player before, and they don’t appear keen to set a new precedent with Tucker.

But Jed Hoyer and the rest of the front office understand that they’ll need to at least try to replace Tucker’s production in the lineup. Luckily, there are many compelling potential replacements available, all of whom will come with a more appealing price tag than King Tucker.

One that has been linked to the Cubs several times is former Houston Astros and Boston Red Sox third baseman Alex Bregman.

Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images / Mark J. Rebilas-Imagn Images

Like New York Mets slugger Pete Alonso (who is another intriguing Tucker replacement for Chicago), Bregman is hitting free agency for the second straight offseason after opting out of the three-year, $120 million deal he signed with the Red Sox last offseason after spending his first nine MLB seasons in Houston.

Bregman hit .273 with an .822 OPS, 18 home runs, and 62 RBIs in just 114 games because he missed about two months with a quad strain. He also earned his first All-Star nod since the 2019 season.

While Bregman does make a lot of sense for Chicago, a November 8 report from MLB.com’s Mark Feinsand raises interesting questions.

Feinsand noted that the Cubs offered Bregman a four-year, $130 million offer last winter. For those keeping track, that’s $10 million more (albeit with one more year) than what he got from the Red Sox.

This begs the questions of why Bregman turned that offer down (especially if he intended to opt out after one season all along), and whether his doing so would suggest that he simply doesn’t want to join the Cubs.

Of course, other factors could have gone into his decision. Perhaps the Cubs’ contract offer didn’t include a player option after 2025, or maybe Bregman just wanted a three-year deal. Or maybe he believed the Red Sox were just the better option for him.

Regardless, news of this past contract offer makes Bregman’s potential future in Chicago somewhat murky.

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