hicago Cubs: Can They Break Through and Secure a Major Free Agent This Offseason?

As the offseason drags on, Chicago Cubs fans are growing increasingly skeptical about their team’s chances of making a significant splash in free agency. With each passing day, the hopes of landing a high-profile free agent seem to diminish.

The front office, led by Jed Hoyer, has shown interest in several top-tier players. Yet, a familiar pattern is emerging: the Cubs, a team historically known for its tight purse strings, are unlikely to outbid larger-market teams with deeper pockets. This was evident in their pursuit of Dylan Cease, where the Cubs were ultimately outbid by a bigger-market team.

The Alex Bregman Saga

One player the Cubs have been linked to in recent reports is Alex Bregman, the star third baseman from the Houston Astros. This connection has been building for some time, with Chicago expressing interest in bolstering their infield. Bregman, an elite talent, has long been one of the most consistent hitters in Major League Baseball.

The situation has taken a twist, however, with the Toronto Blue Jays, who had also been eyeing Bregman, making a surprise move by signing Kazuma Okamoto on January 3. This unexpected signing could now work in the Cubs’ favor. With Toronto potentially out of the running for Bregman, the Cubs find themselves in a better position to land the 29-year-old.

However, the road to securing Bregman is far from clear. The Boston Red Sox and the Arizona Diamondbacks remain serious contenders for his services. Both teams, known for their willingness to spend in free agency, are likely prepared to offer Bregman a more lucrative deal than the Cubs. This could make it difficult for Chicago to close the deal.

The Bo Bichette Opportunity

In addition to Bregman, there’s another elite free agent that the Cubs may be targeting: Bo Bichette. The Toronto Blue Jays shortstop became an unrestricted free agent after a stellar 2025 season. Bichette had an impressive campaign, hitting .311 with an .840 OPS, 18 home runs, and 94 RBIs. His bat was one of the key driving forces behind Toronto’s World Series run, where he continued his hot streak with a .348 postseason average and a .922 OPS.

Bichette’s postseason performance was nothing short of spectacular. In the winner-take-all Game 7 of the World Series, Bichette hit a crucial three-run home run, further cementing his status as a clutch player. Despite the Toronto Blue Jays falling short against the Los Angeles Dodgers, Bichette’s stock is higher than ever.

The Cubs Enter the Bichette Race

In an exciting turn of events, it appears that the Cubs are now actively pursuing Bichette. This was confirmed by New York Post MLB insider Jon Heyman in a January 3 post, where he noted that the Phillies, Yankees, Dodgers, Red Sox, and Cubs are all in the mix for the 27-year-old shortstop. Heyman further highlighted Bichette’s rare ability to hit .300 against fastballs, breaking balls, and changeups/splitters—skills that make him one of the most well-rounded hitters on the market.

This news is both exciting and concerning for Cubs fans. On one hand, it’s reassuring to see the Cubs involved in the chase for a talent like Bichette. On the other hand, the Cubs are competing against some of the most well-funded and aggressive teams in Major League Baseball. The Yankees, Dodgers, and Red Sox have proven time and again that they are willing to spend whatever it takes to land the best players available, making this a high-stakes battle for the Cubs.

Cubs Competing with Big-Market Teams

For the Cubs, competing with the big-market teams isn’t ideal. Historically, the Cubs have struggled to keep pace with the spending power of teams like the Yankees and Dodgers, who routinely bring in some of the best free agents. However, the Cubs’ involvement in the Bichette race is a step in the right direction.

At the very least, it shows that the Cubs are willing to make a push for a high-caliber player. Even if they don’t manage to land Bichette, their efforts demonstrate that the front office is intent on improving the team, and this can only bode well for the future.

Other Cubs News: The State of the Team Heading Into 2026

As the Cubs continue to pursue top free agents, the team is also making headlines for other reasons. There have been reports on the Cubs’ pitching staff heading into the 2025 season, with several players recovering from Tommy John surgeries. The team’s pitching staff, though talented, remains a work in progress, and much will depend on the health and effectiveness of key pitchers in 2026.

Additionally, there are ongoing discussions about the Cubs’ potential moves with players like Kyle Tucker, whose departure seems likely. The Cubs may need to address their outfield situation, and Tucker, if available, could be a key addition to their roster.

Lastly, the Cubs’ minor league system continues to generate excitement, with a top prospect set to break out in 2026. This offers a glimmer of hope for the future, as the team looks to develop homegrown talent that can make an impact at the major league level.

Final Thoughts

As the Cubs look to make a significant move in free agency, the challenge remains the same: competing against bigger-market teams with deeper pockets. The pursuit of Alex Bregman and Bo Bichette is a sign that the Cubs are trying to make a splash, but history suggests they may struggle to outbid the wealthier teams.

Nonetheless, there’s still plenty of time for Jed Hoyer and the front office to make a deal that could reshape the future of the franchise. Whether they land one of these stars or not, Cubs fans will be closely watching the coming months to see if their team can finally break through and secure a game-changing free agent.