As spring training approaches, the offseason for Major League Baseball (MLB) for 2024-25 is drawing to a close. For some players and teams, this winter has not yielded the desired outcomes, prompting discussions about the most significant disappointments this offseason. The analysis includes a mix of players, teams, and broader sentiments surrounding the league. While some entries may be seen as presumptuous—such as Pete Alonso potentially emerging as a winner—the current state of affairs suggests otherwise. Before listing the major losers, it is essential to acknowledge a few honorable mentions.

Starting with third baseman Alex Bregman, his lack of a signed contract at this stage is surprising. Speculation surrounding a potential reunion with the Houston Astros appears tenuous, especially given remarks made by Astros’ general manager Dana Brown during the team's annual media luncheon, where he referred to Bregman in the past tense. Yet, in comparison to other stars still seeking contracts, there remains a possibility for Bregman to secure a market-value deal, with reports indicating that at least one team has made a six-year offer to the veteran.

The Milwaukee Brewers have also faced challenges this offseason. Known for a relatively quiet winter, the team has again adopted a low-profile approach, exacerbated by the loss of shortstop Willy Adames to free agency. Additionally, the trade of star relief pitcher Devin Williams returned only uninspiring assets, leaving the Brewers in a difficult position to improve their roster.