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The Orioles seemingly struck gold with Chris Davis, awarding him a seven-year, $161 million contract after a stellar season. Unfortunately, his performance plummeted thereafter, including a historically poor 2018 season, cementing him as a financial burden for the franchise.
2015 Offseason: Pablo Sandoval
Pablo Sandoval's five-year, $95 million deal with the Red Sox was one of the most bewildering. A drop in work ethic and performance led to Sandoval's exit from the team, leaving a poor legacy behind.
2014 Offseason: Jacoby Ellsbury
Jacoby Ellsbury’s seven-year, $153 million contract with the Yankees became burdensome as injuries derailed his potential performance, resulting in him never being able to make a significant impact for the team.