MLB insider just dragged the Cubs back into the Alex Bregman free agency circus

Here we go again.

Jordan Campbell

Boston Red Sox v Tampa Bay Rays / Maddie Malhotra/Boston Red Sox/GettyImages

Pitching is the focus of the Chicago Cubs' offseason, but the fact remains that they are losing a big piece of their offense in Kyle Tucker. While the Cubs seem to be comfortable with giving more plate appearances to Owen Caissie and Moises Ballesteros in 2026, it stands to reason the team will be opportunistic if one of the top position players on the free-agent market has a sweepstakes that stalls.

Odds would circle Alex Bregman as the likeliest candidate to have his free agency drag out, considering he is likely looking for the long-term contract that alluded him last offseason, but an injury and second-half slump could lead to the same hesitancy teams acted with last offseason.

Last offseason, Bregman's free agency dragged into February, leading to the Cubs trying to take advantage. Their efforts weren't as urgent as the Boston Red Sox, but a creative three-year deal from Boston has allowed the All-Star third baseman to test free agency once again.

ESPN's Jeff Passan does point to the Red Sox wanting to bring Bregman back, but suggests that the Detroit Tigers and Cubs are expected to rejoin the fray this offseason. Passan also mentioned the Philadelphia Phillies as a potential suitor for Bregman.

The Chicago Cubs appear to be circling back to their interest in Alex Bregman from last offseason.

First and foremost, if the Red Sox get as aggressive as they were last offseason in their efforts to bring Bregman back, the Cubs likely won't stand in their way. While the Cubs likely feel the same way about Bregman that they did last winter, the assumption is that if they were going to jump the market for a free agent, it would be for a starting pitcher.

If things get weird between Bregman and the Red Sox, that likely is when the Cubs would enter the picture. Matt Shaw did enough during the second half of the season to suggest he is capable of being the long-term answer at third base, but for a Cubs team entering a season where their chips should be pushed to the middle of the table, they need to find a way to replace the offense they are losing with Tucker's departure.

Adding an offensive upgrade at third base while pushing Shaw to a utility role feels like the easiest way for the Cubs to do so.

Jordan Campbell

For nearly 15 years, Jordan has been a workhorse across the FanSided network - including being the inaugural site expert for Cubbies Crib, as well as a stop at Da Windy City as the site expert. In addition to returning to be a Co-Site Expert at Cubbies Crib, Jordan was previously the Site Expert at Bear Goggles On. In the years since, Jordan has joined FanSided's full-time team, serving as a staff writer for the MLB division. Jordan's work can be seen across the MLB division, including a consistent presence on our Cubs, Twins, Astros, and Tigers sites. Since 2010, Jordan has dedicated his craft to providing insightful commentary on all things Chicago sports, and he has enjoyed his venture into all things Major League Baseball.