The Worst MLB Free-Agent Signings in History

In Major League Baseball, free agency can be a double-edged sword for teams. While it offers a chance to acquire top talent and bolster rosters, it also comes with the risk of costly mistakes. Throughout the history of the sport, there have been signings that left teams regretful, saddled with expensive contracts and underperforming players.

Here’s a rundown of some of the most notorious and ill-fated MLB free-agent signings of all time:

1. Albert Pujols to the Los Angeles Angels (2012): When the Angels signed the legendary Albert Pujols to a 10-year, $240 million deal, they expected to secure one of the game’s greatest hitters. However, Pujols struggled to replicate his stellar St. Louis Cardinals’ form. His production declined, and injuries hampered his performance, making the latter years of his contract a burden on the team’s payroll.

2. Jacoby Ellsbury to the New York Yankees (2014): The Yankees envisioned Ellsbury as a game-changer when they signed him to a seven-year, $153 million contract. Unfortunately, injuries plagued his time in New York, severely limiting his playing time and diminishing his impact on the field. The deal turned into a financial drain for the Yankees.

3. Josh Hamilton to the Los Angeles Angels (2013): Another Angels’ signing gone awry was Josh Hamilton’s five-year, $125 million contract. Despite a successful stint with the Texas Rangers, Hamilton struggled with injuries and inconsistency in Los Angeles. His performance failed to match the expectations set by his hefty contract.

4. Carl Pavano to the New York Yankees (2005): The Yankees signed Pavano to a four-year, $39.95 million deal hoping to bolster their pitching rotation. However, injuries severely limited his time on the field. Pavano made just 26 starts over four years, leaving the Yankees regretting their investment.

5. Chris Davis re-signing with the Baltimore Orioles (2016): After an impressive 2015 season, Davis inked a seven-year, $161 million contract to remain with the Orioles. Unfortunately, his production sharply declined, and he struggled at the plate, becoming a liability rather than an asset for the team.

6. Barry Zito to the San Francisco Giants (2007): Zito’s seven-year, $126 million contract with the Giants didn’t pan out as expected. Despite his success with the Oakland Athletics, Zito struggled in San Francisco, failing to live up to the high expectations set by his massive contract.

These signings serve as cautionary tales for MLB franchises, highlighting the inherent risks of free agency. While some deals result in immediate dividends, others turn into financial burdens, impacting teams for years to come. General managers and team owners must weigh the risks and rewards carefully when pursuing free agents, as the wrong move can have long-lasting consequences on a team’s success and financial stability.