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Chicago Cubs’ Pursuit of Alex Bregman: What’s at Stake This Offseason?

As the Chicago Cubs head into another offseason, many fans are hopeful that the team will make a splash by signing star third baseman Alex Bregman in free agency. Bregman is undeniably one of the most coveted free agent hitters still available, and given the Cubs’ current roster needs, he appears to be the best fit among the top free agents. However, while the signing of Bregman could bolster the Cubs’ offense, it might come with some roster complications that could make this pursuit more difficult than anticipated.

Bregman: The Best Remaining Free Agent Fit

At this point, Bregman is arguably one of the three best hitters remaining in free agency, alongside former Cubs Kyle Tucker and Cody Bellinger. Tucker and Bellinger, both of whom primarily play in the outfield, would add depth to an already crowded Cubs outfield, which diminishes their appeal in Chicago. Bregman, on the other hand, would provide the Cubs with the much-needed impact bat to add to their infield. A three-time All-Star and two-time World Series champion, Bregman is undoubtedly a player that could elevate the Cubs’ chances of returning to the postseason and winning their first championship since 2016.

However, signing Bregman is not without its challenges. The Cubs’ current infield situation complicates matters, as Bregman would almost certainly force Matt Shaw to second base, displacing current second baseman Nico Hoerner. Hoerner, who will become a free agent after the 2026 season, might then either be traded or leave the team if he doesn’t receive an extension. This is a risk that Cubs management would need to weigh carefully as they make their decision on whether or not to pursue Bregman.

Should the Cubs Pursue Bregman Now and Worry About the Rest Later?

Despite the potential roster shakeup, there’s an argument to be made that the Cubs should prioritize signing Bregman and deal with the ripple effects later. Bregman is an elite talent—he has consistently been one of the best third basemen in the game and has delivered in postseason situations, making him an undeniable asset for any team looking to contend. Adding Bregman to the Cubs lineup would undoubtedly increase their chances of competing at the highest level and could help them secure that elusive championship.

Additionally, with the Cubs already having a strong outfield, the signing of Bregman would allow them to focus on bolstering other areas of the roster in future offseasons. If the Cubs could acquire Bregman without sacrificing key prospects or assets, it may make sense to pull the trigger now and worry about other roster moves later.

The Latest Buzz: Cubs Falling Behind in Bregman Sweepstakes

While the Cubs have been linked to Bregman throughout the offseason, the latest reports suggest that they are not being as aggressive as some of the other teams in pursuit of the star third baseman. In a January 1 article by MLB.com’s Mark Feinsand, sources indicated that the Toronto Blue Jays and Arizona Diamondbacks may be the frontrunners for Bregman’s services. The Boston Red Sox were also mentioned as a possible landing spot for the third baseman, though the reunion remains a long shot.

Feinsand’s article further revealed that while the Cubs and the Detroit Tigers have been connected to Bregman at various points in the offseason, it seems that Chicago is not being viewed as one of the more aggressive teams in the race. This lack of urgency could be a sign that the Cubs may not be willing to commit the necessary resources to outbid other teams, which would be a disappointing turn for many fans hoping for a major splash this offseason.

Should the Cubs Focus on a Starting Pitcher Instead?

From a roster-building perspective, it could make more sense for the Cubs to prioritize signing one of the high-end starting pitchers available in free agency. With names like Framber Valdez, Ranger Suarez, and Zac Gallen on the market, adding a frontline starter would bolster the Cubs’ pitching rotation, which has been one of the team’s most pressing concerns over the past few seasons.

The Cubs have a solid foundation in their lineup but could benefit greatly from strengthening their pitching staff if they want to compete for a division title. Adding a pitcher of Valdez’s, Suarez’s, or Gallen’s caliber could provide the Cubs with the stability they need in the rotation while allowing them to pursue other offensive options down the road.

The Potential Fallout from a Quiet Offseason

As the Cubs’ offseason progresses, many fans are growing increasingly frustrated at the lack of major moves so far. If the biggest move the team makes this winter is the signing of a middle-reliever like Phil Maton, it will be difficult for the fanbase to ignore the disappointment, especially after losing out on someone like Kyle Tucker, who would have significantly upgraded the Cubs’ outfield.

If the Cubs don’t land Bregman, they may face some tough questions about their offseason strategy and long-term goals. Fans will want to see the front office show a stronger commitment to winning in the short term, especially with key players like Bellinger and Tucker having left the team. It remains to be seen whether Bregman will be the key addition the Cubs need, but at this point, the team may need to make a bold move soon if they want to stay competitive in a crowded NL Central division.

Final Thoughts: Is Bregman the Right Move for the Cubs?

As the Cubs’ offseason unfolds, it’s clear that the pursuit of Alex Bregman is not without its complications. The third baseman would undoubtedly be a fantastic addition to Chicago’s roster, but the timing and fit with the current roster leave some questions unanswered. If the Cubs are serious about making a deep playoff push, they will need to evaluate all their options carefully. Whether they go all-in on Bregman or shift their focus to strengthening their pitching staff, this offseason could be pivotal in determining whether the Cubs return to championship contention. Only time will tell if the Cubs can make the moves necessary to bring them back to the top.