Last Updated: June 17th, 2026 by Michael Schatz
Major League Baseball history is filled with free agent signings that teams wish they could take back. From massive contracts that didn’t pan out to letting future Hall of Famers slip away, here are some of the most regrettable free agent decisions in National League history.
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Jeffrey Hammonds’ Brewers Bust
In 2000, the Milwaukee Brewers made a costly mistake by signing Jeffrey Hammonds to a three-year, $22.2 million contract. The deal came after Hammonds posted an impressive .924 OPS with the Colorado Rockies, but the Brewers failed to account for the infamous Coors Field Effect, which artificially inflated his statistics.
Tino Martinez’s Cardinals Disappointment
The Cardinals signed Tino Martinez to a three-year, $21 million contract in 2002 as Mark McGwire’s replacement. The move proved disastrous as Martinez struggled to adapt to his new team, posting a dismal 2-for-25 performance in the 2002 postseason. His tenure was cut short when the team traded him to Tampa Bay before his contract expired.
Cubs Let Greg Maddux Slip Away
In one of baseball’s biggest blunders, the Cubs lost Greg Maddux in 1992 right after he won his first Cy Young Award with the team. The decision proved catastrophic as Maddux went on to win three more consecutive Cy Young Awards with the Atlanta Braves, cementing his legacy as one of baseball’s greatest pitchers.
Pirates Lose Barry Bonds
The Pirates’ loss of Barry Bonds in 1992 marked a turning point in baseball history. While retaining Bonds might have been impossible for the small-market Pirates, his departure dramatically altered the course of MLB history. Bonds would go on to become baseball’s all-time home run leader with the Giants.
Eric Milton’s Cincinnati Disaster
The Reds signed Eric Milton to a three-year, $25.5 million contract in 2005, failing to consider how their ballpark would affect his pitching style. As a fly-ball pitcher in a hitter-friendly park, Milton struggled significantly, teaching the Reds a costly lesson about their new stadium’s characteristics.
Diamondbacks’ Russ Ortiz Mistake
The Diamondbacks’ four-year, $33 million investment in Russ Ortiz in 2004 proved disastrous. Ortiz made just 28 starts for Arizona, posting a terrible 5-16 record with a 7.00 ERA. This signing stands as one of the worst in franchise history, providing minimal return on a significant investment.
Dodgers’ Darren Dreifort Debacle
The Dodgers’ five-year, $55 million commitment to Darren Dreifort in 2000 backfired spectacularly. Dreifort managed only 200 innings throughout the entire contract before retiring, making this one of the most regrettable contracts in Dodgers history.
Barry Zito’s Giants Contract
The Giants’ seven-year, $126 million investment in Barry Zito in 2006 yielded mixed results. While his ERA increased significantly from his Oakland days, Zito contributed to two World Series championships. Despite not meeting financial expectations, his positive fan relationship somewhat softened the blow of this massive contract.
Mike Hampton’s Rocky Mountain Low
The Rockies’ eight-year, $121 million commitment to Mike Hampton in 2001 became infamous when he cited Colorado’s school system as his reason for signing. The relationship was short-lived, as Hampton departed for Atlanta just two years into the massive contract, making it one of the most notorious free-agent failures in MLB history.
Oscar Gamble’s Short-Lived Padres Stint
The Padres signed Oscar Gamble to a six-year, $2.8 million contract in 1978, but the relationship was remarkably brief. Despite being known for his iconic afro and solid hitting, Gamble spent just one season with San Diego – the worst of his career. The short-lived experiment ended quickly, making it one of the Padres’ most regrettable free agent decisions.