The Chicago Cubs are not messing around in 2026. In a move that sent shockwaves through Major League Baseball, the North Siders have signed star third baseman Alex Bregman to a five-year, $175 million contract, marking the third-largest deal in franchise history and signaling the organization's intent to return to championship contention.

Bregman, a two-time World Series champion during his tenure with the Houston Astros, spent just one season with the Boston Red Sox before opting out of his contract to test free agency once again. The Cubs ultimately outbid Boston's reported $165 million offer by $10 million to secure one of the most complete players in baseball.

The 31-year-old infielder proved he still has plenty left in the tank during his 2025 campaign at Fenway Park. Bregman slashed .273/.360/.462 with 18 home runs, posting an impressive 128 OPS+ that placed him well above league average. His combination of plate discipline, power, and defensive versatility made him one of the most coveted free agents on the market.

From a contract structure standpoint, the Cubs have built in some financial flexibility. The deal includes $70 million in deferred money, a strategy designed to lower the competitive balance tax impact and give Chicago more room to maneuver in future offseasons. Bregman receives a full no-trade clause, giving him complete control over his destination, while the contract contains no opt-outs that might allow him to leave early.

The signing does create an interesting roster puzzle for Cubs president Jed Hoyer and manager Craig Counsell to solve. Chicago already boasts a talented infield that includes Gold Glove second baseman Nico Hoerner and highly-regarded third baseman Matt Shaw, who emerged as a key piece of the Cubs' future during recent seasons.

With Bregman now manning third base at Wrigley Field, the organization faces a decision. Trading either Hoerner or Shaw would bring back significant value and open a clear path for Bregman, while also addressing other roster needs. Hoerner's elite defense and contact-oriented approach would appeal to numerous contenders, while Shaw's youth and upside could net a substantial return in any trade package.

For Cubs fans who have watched their team struggle to recapture the magic of the 2016 World Series championship, Bregman represents exactly the type of proven winner the franchise needs. His postseason experience is extensive and impressive, having played in multiple World Series and countless high-leverage playoff situations during his time in Houston.

The veteran presence Bregman brings to the clubhouse cannot be understated either. Young Cubs players will benefit from sharing a locker room with someone who has performed on the biggest stages baseball has to offer.

Chicago's front office clearly believes the time is now to push their chips to the center of the table. The National League Central remains a winnable division, and adding a player of Bregman's caliber instantly elevates the Cubs' ceiling.

As spring training approaches, all eyes will be on Wrigley Field to see how Counsell deploys his revamped roster. One thing is certain: with Alex Bregman anchoring the hot corner, the Cubs have transformed themselves from pretenders into legitimate contenders. The Friendly Confines just got a whole lot more dangerous for opposing pitchers.