MLB Offseason 2026: Evaluating the Biggest Winners and Losers

With spring training on the horizon, the 2026 MLB offseason has officially concluded, leaving a clear trail of strategic triumphs and puzzling missteps. The landscape of the league has been reshaped by blockbuster signings, surprising trades, and notable inaction from several would-be contenders. As rosters are finalized, it's time to evaluate which teams and players positioned themselves for success and which may face an uphill battle in the coming season. This analysis, drawing on key offseason developments, highlights the definitive winners and losers from a winter that saw the rich get richer and left several contenders with more questions than answers.

Definitive Winners: Teams That Made Major Moves

Several franchises made decisive moves to bolster their championship aspirations, with one team continuing its reign as the offseason's undisputed champion.

Los Angeles Dodgers: The Dynasty Builds

The two-time defending World Series champions, the Los Angeles Dodgers, delivered another masterclass in roster construction. Their signature move was the stunning acquisition of elite closer Edwin Díaz on a three-year, $69 million contract, a deal that surprised the league and directly addressed the bullpen as the team's only perceived flaw. This move, coupled with their already star-studded roster featuring Shohei Ohtani and Yoshinobu Yamamoto, solidifies them as the overwhelming favorites for the 2026 title. With a payroll exceeding $400 million, the Dodgers have successfully translated financial might into sustained on-field dominance.

Chicago Cubs: A Big-Market Flex

The Chicago Cubs responded aggressively to the market, making a significant statement by signing third baseman Alex Bregman to a five-year, $175 million contract. This deal, the third-largest in franchise history, signals a willingness from the big-market Cubs to flex their financial power in free agency. Projection systems like PECOTA now place the Cubs among the top teams in the National League, tied with the Braves and Mets. While questions remain about their pitching staff, the addition of Bregman dramatically boosts their lineup and championship credibility.

Notable Losers: Teams with Questionable Winters

Conversely, a number of teams with playoff aspirations had offseasons marked by inactivity or puzzling roster decisions, leaving their fanbases concerned.

Houston Astros: A Step Backwards?

The Houston Astros, who missed the postseason for the first time since 2016, failed to make significant improvements to their roster. Despite adding Japanese pitcher Tatsuya Imai, the team enters spring training with an awkward positional logjam, potentially forcing a trade of a player like Isaac Paredes or Christian Walker. FanGraphs projects the Astros to regress to 81 wins, suggesting their inactivity this winter may not be enough to return them to October baseball, making it a flat and concerning offseason.

San Diego Padres: Handcuffed and Weakened

Financial constraints related to player salaries and a potential franchise sale severely limited the San Diego Padres. The team failed to adequately replace the losses of key players like Dylan Cease, Robert Suarez, and Luis Arraez. Their starting rotation, now without Cease and Yu Darvish, is projected to be among the worst in the league. Without adding elite talent or addressing a lineup that ranked 28th in home runs last season, the Padres appear significantly weaker, setting the stage for a potentially difficult 2026 campaign.

Individual Winners and Losers

The offseason also had profound implications for individual players, with some securing life-changing deals and others facing unexpected market realities.

Winner: Tarik Skubal

Detroit Tigers ace Tarik Skubal, a two-time Cy Young winner, made arbitration history. By comparing himself to any major-league pitcher in his prime, Skubal and agent Scott Boras secured a record $32 million salary for 2026, shattering the previous arbitration record. This landmark deal not only rewards Skubal's elite performance but also pushes the boundaries of the arbitration system, setting a new precedent for top-tier talent.

Winner: Pete Alonso

First baseman Pete Alonso achieved his goal of a long-term contract with a contender, signing a five-year, $155 million deal with the Baltimore Orioles. For Alonso, this move provides financial security and a chance to compete, while for the Orioles, it marks a long-overdue foray into signing a top-tier, right-handed power bat to stabilize their young lineup.

Loser: Munetaka Murakami

Japanese slugger Munetaka Murakami experienced one of the most disappointing market outcomes. Hailed as the next great Japanese phenom after hitting 56 home runs in NPB in 2022, he was expected to command a contract north of $150 million. Instead, he signed a modest two-year, $34 million deal with the Chicago White Sox. Concerns about his swing-and-miss rate against NPB pitching evidently scared off contenders, resulting in a significant underpayment for his perceived talent.

The Complex Cases: Winners(ish) and Losers(ish)

Some teams' offseasons defy simple categorization, featuring both brilliant moves and lingering concerns.

Toronto Blue Jays: Pitching Up, Hitting Down

The Blue Jays made a massive splash by signing ace Dylan Cease to a franchise-record seven-year, $210 million deal, giving them one of baseball's best rotations. However, their lineup is objectively weaker after failing to sign Kyle Tucker and not re-signing homegrown star Bo Bichette. This imbalance between a strengthened pitching staff and a diminished offense prevents them from being a clear-cut winner.

New York Yankees: Running It Back

The New York Yankees' biggest move was re-signing outfielder Cody Bellinger, a perfect fit. However, their overall inactivity in a market filled with top talent was underwhelming. While they remain a strong team projected to win their division, the front office's decision not to aggressively add more pieces around Aaron Judge in the final years of his prime leaves room for criticism regarding their championship urgency.

Conclusion: A Season Shaped by Winter

The 2026 MLB offseason has dramatically altered the league's hierarchy. The Los Angeles Dodgers have further cemented their status as a modern dynasty, while teams like the Cubs and Orioles have signaled serious intent. Conversely, the Astros, Padres, and Brewers—who spent zero dollars on major-league free agents—face justified skepticism. As players report to camp, the consequences of these winter decisions will begin to unfold on the field, setting the narrative for a season where the groundwork for success or failure was laid months in advance.