fifteen unclaimed free agents and trade deals that, if successful, could have significantly altered the course of Cardinals franchise history
The St. Louis Cardinals have a rich history, but it could have been even more illustrious had they executed some key free agency and trade market opportunities differently. In a series of near-misses, the team has found itself on the wrong side of deals that, in hindsight, could have significantly altered their trajectory.
The Marcell Ozuna Trade (2017)
One of the most notable near-misses was the trade that sent Zac Gallen, who later became a multiple Cy Young Award finalist with other teams, including a strong performance in 2020-2023, to the Miami Marlins in exchange for Marcell Ozuna. Retaining Gallen instead could have dramatically bolstered the Cardinals' pitching strength and overall team success. This trade is now viewed retrospectively as a significant misstep for the Cardinals.
Prospects on the Line
Alongside Gallen, prospects like Sandy Alcantara (ranked #6 in MLB.com's Cardinals prospects list in 2017) were involved or considered in trades at the time. Avoiding these moves or structuring different trades involving these top prospects might have benefited the team substantially.
The Brendan Donovan Conundrum (2025)
Brendan Donovan, one of the Cardinals' best players and a flexible, reliable infielder/outfielder, has been a subject of trade considerations during the team's ongoing rebuild. His contract timeline may not match the team’s competitive window, and trading Donovan sooner or leveraging his trade value aggressively at the deadline could have brought back significant prospect capital to accelerate the rebuild.
Free Agent and Trade Deadline Opportunities
The Cardinals have been in a phase of dealing with expiring contracts and evaluating trade deadline strategies. For instance, they did not acquire a right-handed bat at some deadlines despite lineup needs. Missed opportunities for adding established hitters or bullpen arms via trades or free agency at critical moments could have altered their offensive or pitching depth.
Strategic Misses in Contending Windows
The Cardinals' "win-now" moves have occasionally involved trading away prospects who blossomed elsewhere (e.g., Gallen). This pattern suggests that more careful prospect valuation or resisting aggressive trades might have preserved a stronger talent base.
While explicit details of 15 individual near-misses are not exhaustively listed here, the Marcell Ozuna-Zac Gallen trade stands as the most cited single pivotal near-miss. Other prospects and key players like Sandy Alcantara and Brendan Donovan represent similar critical trade/free agency decisions that could have shaped the franchise’s history differently.
For a comprehensive list of 15 specific near-miss opportunities, further detailed historical analysis beyond the current search results would be required, as current available sources discuss major examples rather than a complete catalog.
The St. Louis Cardinals could have enhanced their sports glory, especially in baseball (MLB), had they retained Zac Gallen, who became a multiple Cy Young Award finalist, in the Marcell Ozuna trade (2017). Simultaneously, the Cardinals' reluctance to reconsider or avoid trades involving prospects like Sandy Alcantara might have significantly bolstered their success. In addition, neglecting to acquire a right-handed bat at some trade deadlines despite lineup needs and failing to add established hitters or bullpen arms via trades or free agency could have bolstered their offensive or pitching depth.
