Last offseason, the Chicago Cubs made a play to sign veteran star infielder Alex Bregman. Unfortunately, Jed Hoyer and company lost the bidding war to the Boston Red Sox.

After his first season with the Red Sox, Bregman has now entered free agency once again. This time around, it sounds like the Cubs have renewed their interest from last year.

Bregman would be a big upgrade, especially offensively, over what Chicago got last season from Matt Shaw. With Kyle Tucker expected to leave town in free agency, the Cubs are going to need more offensive firepower. He’s also a capable defensive third baseman.

With that being said, one MLB insider spoke out with an update about Chicago’s interest in Bregman.

Bruce Levine of 670 The Score has shared why Bregman is of such interest to the Cubs.

“Alex Bregman this free agent year, without losing a draft pick, ( qualifying offer) is more attractive to teams like the Cubs and Tigers,” Levine wrote. “.821 OPS despite playing only 114 games.Cubs offer last winter was 4 years ,$115 million.Right handed pop might be the way to go for Cubs.”

Alex Bregman, Chicago Cubs — Sep 24, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) hits a single against the Toronto Blue Jays in the first inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images

Throughout the course of the 2025 MLB season with Boston, Bregman ended up playing in 114 games. He hit 18 home runs, drove in 62 RBI, and produced a slash line of .273/.360/.462.

At 31 years old, Bregman still has quite a bit of good baseball left in the tank. If Chicago is serious about signing him, Hoyer is going to have to get aggressive. The Cubs are going to need to offer him years and a lot of money to get a deal done.

Will Chicago actually be willing to pay out the kind of contract that it will take to sign Bregman? That remains to be seen, but the team badly needs help. If the front office isn’t aggressive, the Cubs could see a big amount of regression during the 2026 MLB season.

Hopefully, the fans will get what they want this offseason. It doesn’t necessarily have to be Bregman, but fans want to see Chicago get aggressive and make win-now moves.

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