Cubs Weigh Matt Shaw’s Rise Against Alex Bregman’s Free-Agent Return

The Chicago Cubs enter the Winter Meetings with a delicate balancing act between their young core and high-profile free-agent opportunities. Matt Shaw’s emergence at third base has energized fans and provided clarity on the infield, while Alex Bregman’s return to free agency presents the chance to add a proven, impactful bat.

Bregman, a three-time All-Star and two-time World Series champion, opted out of the Red Sox after a solid 2025 season, hitting .273/.360/.462 with 18 home runs across 114 games. His presence on the market commands attention and reshapes strategic conversations for teams like Chicago.

Meanwhile, Shaw solidified his role as a reliable everyday third baseman. He combined strong defensive skills with poise at the plate, proving he could handle the position under the bright lights of Wrigley Field. His growth provides stability, but it also complicates potential roster changes involving Bregman.

The Cubs also feature Nico Hoerner at second base, a team leader and anchor, which limits positional flexibility. Any significant roster addition must account for the existing structure, creating a complex decision-making environment as free agency unfolds.

1. Shaw’s Role and Impact

Matt Shaw’s breakout season offered the Cubs a glimpse of their future core. Defensively sound and offensively poised, Shaw has established himself as a key contributor at third base. His emergence has reduced uncertainty around a position the Cubs needed to solidify. Shaw’s versatility is a potential asset if the team adds a high-profile bat. The front office could explore rotating him between third, second, or designated hitter duties, testing his flexibility to accommodate roster upgrades. While trade interest in Shaw could theoretically arise, the likelihood appears low. Chicago seems committed to building around its young talent, suggesting Shaw’s long-term role is secure unless an extraordinary opportunity presents itself. The team faces a strategic question: does adding Bregman enhance the lineup without disrupting the growth trajectory of its rising star? Shaw’s development and performance will influence every move Chicago considers during the Winter Meetings.

2. Bregman’s Potential Influence

Alex Bregman represents an immediate offensive upgrade. His experience and postseason success could lift the clubhouse and provide a veteran presence the Cubs value, especially in high-pressure situations. Adding Bregman would instantly strengthen the lineup, but Chicago has demonstrated the ability to win without him. Shaw’s steady play at third base suggests that the Cubs can balance youth and veteran influence effectively. Integrating Bregman would require careful roster management. Position rotations, playing time, and lineup construction must be addressed to maintain harmony while maximizing overall production. Ultimately, Bregman’s arrival could accelerate the Cubs’ competitive window, but it also introduces strategic questions regarding Shaw’s role and long-term development. The team must weigh immediate gains against sustaining a promising young core.

3. Strategic Crossroads

The Cubs’ offseason strategy hinges on balancing proven talent with emerging stars. Shaw’s presence provides stability and potential flexibility, while Bregman’s availability offers a rare opportunity to bolster the lineup immediately. Chicago’s front office must decide whether to prioritize long-term development or pursue a high-impact free-agent addition that could shift the team’s competitive trajectory. Each option carries risks and rewards, and the decision will shape roster construction for years to come. As the Winter Meetings progress, the organization’s choices will signal its priorities to both fans and the league. How aggressively the Cubs pursue Bregman—and how they integrate Shaw into the equation—will define the team’s direction heading into 2026. Shaw’s emergence and Bregman’s potential addition represent a critical intersection of youth and experience, forcing Chicago to navigate one of its most consequential offseasons in recent memory.