2025-26 MLB Offseason Grades: Cubs Land Bregman While Orioles Build a Juggernaut
The 2025-26 Major League Baseball winter has been one of the most volatile and expensive in the history of the sport. With franchise cornerstones changing zip codes and front offices committing hundreds of millions of dollars to secure postseason windows, the competitive landscape has been fundamentally reshaped. Our comprehensive 2025-26 MLB offseason grades evaluate the biggest winners and losers of the winter, providing a deep dive into the finalized deals that will define the upcoming season.
The North Side Splash: Chicago Cubs Land Alex Bregman
Grade: A-
The Chicago Cubs made the loudest statement of the early winter by securing Alex Bregman on a five-year, $175 million contract. For a Cubs team that has struggled to find consistent production and veteran leadership at the hot corner, Bregman represents a massive upgrade. His postseason pedigree and elite on-base skills provide a perfect anchor for the middle of the Chicago batting order.
While $35 million annually is a steep price for a player entering his age-32 season, the Cubs are clearly in a "win-now" mode. By prying Bregman away from the Houston Astros, Chicago has not only filled their biggest offensive void but also added a championship-caliber presence to a clubhouse that is desperate to return to the top of the NL Central.
Baltimore’s Power Play: Pete Alonso and Shane Baz
Grade: A+
The Baltimore Orioles have officially graduated from a "young team on the rise" to a legitimate American League juggernaut. This winter, the Orioles addressed their two most glaring needs by signing Pete Alonso to a five-year, $155 million deal and securing elite closer Ryan Helsley in free agency. Alonso, who leaves the New York Mets after a storied tenure, brings a consistent 40-home run threat to a roster already stacked with young talent like Adley Rutschman.
The Orioles also made significant waves regarding their pitching staff. In a major roster shakeup, Baltimore acquired Shane Baz to solidify the rotation. To facilitate their aggressive pursuit of veteran talent, the Orioles traded Grayson Rodriguez to the Los Angeles Angels in a deal that brought outfielder Taylor Ward to Camden Yards. While losing a young arm like Rodriguez is difficult, the addition of Baz and the lockdown ninth-inning security of Helsley signal that Baltimore's ownership is fully committed to maximizing their current championship window.
The Mets’ Massive Infield Overhaul
Grade: B+
Despite losing Alonso, the New York Mets were perhaps the busiest team in baseball. Steve Cohen’s front office pivoted quickly, rebuilding their entire middle infield through a combination of high-priced free agency and aggressive trades. The Mets signed Bo Bichette to a three-year, $126 million contract, moving him away from the Toronto Blue Jays to serve as a cornerstone of their new-look offense.
The Mets didn't stop there. They also acquired Marcus Semien in a blockbuster trade with the Texas Rangers and signed veteran Jorge Polanco to bolster their depth. To solidify the bullpen, they landed one of the best relievers in the game, Devin Williams. While the total expenditure is eye-popping, the Mets have effectively replaced Alonso's production with a more balanced, high-contact lineup. The only question remains whether this veteran-heavy infield can maintain health throughout the 162-game grind.
Toronto Rebuilds the Rotation: The Dylan Cease Megadeal
Grade: B
The Toronto Blue Jays took a calculated risk this winter, shifting their focus from the lineup to the mound. After losing Bichette, the Jays invested heavily in pitching by signing Dylan Cease to a seven-year, $210 million contract. Cease has proven to be one of the most durable and high-strikeout starters in the league, and he immediately slots in as the ace of a pitching staff that is looking to reinvent itself.
The $210 million commitment is a significant gamble on a pitcher’s long-term health, especially as the team saw Shane Baz depart for Baltimore. However, the Blue Jays needed a front-line starter to compete in the gauntlet of the AL East. While the loss of Bichette leaves a hole at shortstop that may be difficult to fill with internal options, the acquisition of Cease ensures that Toronto will have a chance to win every fifth day.
2025-26 MLB Offseason Grades: Evaluating the Rest of the Field
Grade: C+ to B-
Other notable moves across the league have further shaped the 2026 projections. The Los Angeles Angels significantly upgraded their pitching staff by acquiring Grayson Rodriguez, giving them a potential long-term anchor for their rotation. Meanwhile, the St. Louis Cardinals have entered a retooling phase, and the Philadelphia Phillies have remained steady, relying on their core of JT Realmuto, Kyle Schwarber, and Ranger Suarez.
As we look toward Spring Training, these 2025-26 MLB offseason grades reflect a league that is increasingly divided between those willing to spend at the top of the market and those looking to rebuild through the draft. The balance of power has shifted toward the East, but as the Cubs and Orioles have shown, aggressive moves on the trade and free-agent markets can change the trajectory of an entire division overnight.
