The Chicago Cubs have made a move in their efforts to sign Alex Bregman by proposing a four-year deal with multiple opt-outs. Despite ballpark concerns about the slugger, the Cubs’ bold move contrasts with reports suggesting that other contenders like the Houston Astros and Boston Red Sox have shifted their focus away from pursuing the All-Star third baseman.

Despite Bregman’s track record—winning two World Series titles and a career .870 OPS in the postseason along with field skills at third base. However, uncertainties surround how well he would adapt to playing at Wrigley Field in Chicago. Taking into account the stadium’s dimensions and weather conditions known for challenging right-handed pull hitters like Bregman makes it hard to predict if he can keep up his offensive performance in such an environment.

Alex Bregman Deal: A Smart Signing or a Risky Gamble?

Cubs Zone posted little information about the Cubs’ offer to Alex Bregman on X. They wrote, “The Cubs reportedly have a “creative, potentially unprecedented” contract offer out to Alex Bregman, per Matthew Trueblood”. Also, “the deal is believed to be worth around $30 million annually over four years, with multiple opt-outs.”

With the market thinning, the Cubs saw an opportunity to strike late. Their offer reportedly pays around $30 million per year, possibly exceeding the $31.35 million AAV of Rafael Devers’ contract—a key benchmark for Bregman and his agent, Scott Boras. The inclusion of multiple opt-outs aligns with Boras’ usual strategy of maintaining flexibility, much like the Cubs’ deal with Cody Bellinger last offseason.

Despite the Cubs’ aggressive approach, some analysts question whether Wrigley Field suits Bregman’s hitting profile. ESPN’s Jesse Rogers bluntly stated on a podcast with Buster Olney that Alex Bregman should “avoid the Cubs at all costs” citing the park’s dimensions, wind patterns, and pitcher-friendly conditions.

Wrigley Field’s tall outfield fences and unpredictable wind currents often suppress right-handed power hitters. Bregman, whose home run power relies heavily on pulling the ball to left field, may struggle to replicate his Minute Maid Park success in Chicago’s tougher environment. Historically, right-handed hitters with gap-to-gap power—like Bregman—have seen their numbers dip at Wrigley, especially in cold early-season games.

Nevertheless, Chicago appears willing to gamble. If Bregman believes in his ability to adjust, he may accept the Cubs’ offer—especially since his other options are sadly dwindling. The decision now rests with him: short-term flexibility with a questionable park fit or a longer-term deal elsewhere?

Financial Implications: Can the Cubs even afford Bregman?

The Cubs must navigate a tight financial situation if they intend to sign Alex Bregman without exceeding the competitive balance tax (CBT) threshold. They currently have just over $35 million in space before hitting the first CBT penalty level, meaning a deal averaging $30 million per year would leave them with minimal financial flexibility for other roster needs. With bullpen help, catching depth, and additional lineup reinforcements still on their checklist, the Cubs must carefully structure Bregman’s contract to avoid handcuffing themselves financially for the 2025 season.

One possible solution is the front-loaded, opt-out-heavy structure similar to Cody Bellinger’s deal, which allowed Chicago to defer some costs while maintaining payroll flexibility. However, if Bregman underperforms or struggles with Wrigley’s conditions, the Cubs could be left paying a premium for declining production. Additionally, if he opts out early, they risk losing him without long-term stability, potentially disrupting their infield plans. Balancing Bregman’s contract against their broader roster needs presents a high-stakes financial gamble for Chicago’s front office.

With Alex Bregman’s market options shrinking, Chicago must weigh the risk of a high-AAV deal with multiple opt-outs. Should Bregman take the plunge and embrace the challenge, or wait for a more favorable opportunity elsewhere?