15 worst New York Yankees free agent signings in franchise history

Minnesota Twins v New York Yankees
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6. Jose Contreras: Four Years, $32 Million, 2002

Jose Contreras was the second-to-last great example of a bygone era of baseball, where the Boston Red Sox tried their darndest to steal targets away from the Yankees, only to be left holding an exploding banana cream pie instead.

The Yankees somehow added Contreras, a Cuban defector, after the 2002 season when he had previously been in Boston's clutches. They did the same with A-Rod the next winter. Then, the world imploded upon itself.

Contreras was actually quite good in his first season in the Bronx, especially as a starter. He dealt with shoulder issues, but went 6-1 with a 2.34 ERA as a starting pitcher during his rookie season.

Unfortunately, the postseason did not go well; seven earned runs and seven walks allowed in 11 innings across eight outings/two series. That should've been expected, though, considering he went 1–1 with a 7.43 ERA out of the 'pen during the regular season.

Ultimately, the injury issues returned during his sophomore season, and Contreras was dealt to the White Sox midseason ... where he won a World Series as part of a super-rotation of strange names (Jon Garland? Freddy Garcia?) and made an All-Star team. Acceptable career. Brutal Yankee. Sox win this round -- Sox of both colors.