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The Padres' seven-year, $144 million deal with Eric Hosmer is often pointed at as a classic mistake. After an impressive final season with the Royals, Hosmer's time with the Padres saw his numbers decline and performances fail to match the hefty contract.
2017 Offseason: Yoenis Cespedes
The Mets' decision to grant Yoenis Cespedes a four-year, $110 million deal was rooted in hope after a memorable 2015 season. However, injuries and off-field incidents plagued his tenure, and he eventually became known more for his absences than his contributions.