Chicago Cubs should sign this World Series champion in free agency

The Chicago Cubs are in a position where they are looking to add premier players to bolster the roster. After making the playoffs in 2025, this offseason is pivotal in making sure they remain competitive. The focus of the fanbase has been the outfield, but one infielder may be in a position to join the team and make an immediate impact. Let’s take a deeper dive into this report and discuss why this would make sense for the Cubbies this offseason.

Chicago Cubs interested in adding Alex Bregman

In a report published by Patrick Mooney and Sahadev Sharma of The Athletic, the Chicago Cubs “have shown renewed interest” in third baseman Alex Bregman. The two sides had conversations during spring training last year before he signed with the Boston Red Sox. Last season, the Cubs offered a four-year, $115 million contract with opt-out clauses after the second and third seasons, but he would not sign.

Bregman had a good season with the Red Sox as he would have a .821 OPS with 18 home runs, 62 RBI, and a 51:70 walk-to-strikeout ratio over 114 games. While Chicago has Matt Shaw at third base, this would fill a major hole in the lineup to replace Kyle Tucker. The number-two prospect in the organization, Moises Ballesteros, is also on the verge of a call-up, so this move would likely have other factors. Could signing Bregman lead to a trade for some pitching?

The Chicago Cubs would be a better offensive team with Alex Bregman than they are without him signing. With the left side of the infield being Bregman and Dansby Swanson, that is a good building block to success. They are going to be in a battle for his services, as the Red Sox are still reportedly interested in a return as well as some other teams vying for him.

Why Bregman to the Cubs makes sense

The Chicago Cubs have made things clear: they are looking to win games. In order to do that, they need to outclass the Milwaukee Brewers and signing Bregman allows the gap to be lessened. Even entering his age 32 season, Bregman is an outstanding hitter and won the 2024 Gold Glove at third base, giving the infield defense a boost. If Chicago is going to be outbid by another team for Kyle Tucker, this gives the team a chance to keep an elite hitter on the roster.

Bregman has played at least 114 games in each of his last four seasons, so he is going to be on the field. He also brings not only a pair of championships, but production in the playoffs. In 102 career playoff games, he has a .791 OPS with 19 home runs and 55 RBI, making him one of the elite playoff performers. Yes, it would be another right-handed hitter in the lineup, but Bregman is a contact-first player with pop in the bat.

He will also take pressure off the pitching staff by playing an elite third base. He has played 129 career games at shortstop and nine at second base, so there is the potential of moving him around the diamond if needed. This would be a great signing, and the Cubs should be all in on adding Bregman to the middle of their lineup for the 2026 season.

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