Yankees Worst Free Agent Signings All-Time

WORST YANKEES FREE AGENT SIGNINGSRecently, Adam and Rich discussed the Top-5 Greatest Yankees of All-Time.  That got both of them thinking, “If those are the best players in Yankees history, who are the worst?”  With that thought bouncing in their minds, they decided to figure out which players comprise the Yankees Worst Free Agent Signings in franchise history.

All teams have bad free agent signings.  The player either was signed way past their prime, what the player accomplished for the team was simply was not worth the money spent, or injuries cause the player to simply not be able to play for the team.  The Yankees are no exception to this.  All Yankees fans have their favorite “worst free agent signings”, but here are Adam and Rich’s choices for the worst signings.

The countdown will be from the fifth worst down to the absolute worst free agent signing in Yankees history.  At the end, you will be able to vote for your choice of the worst signing. Grab a seat and some popcorn, because we now begin down the terrifying path of the worst signings in Yankees history:

Yankees Worst Free Agent Signings Number 5

Adam – The fifth spot is tough but I have to award the dubious honor to Javier Vazquez. The Yankees signed Vazquez in 2004 out of Montreal to a four-year deal worth over $40 Mil. At face value, the deal seemed good and Vazquez was only 27 years old. At the time of the signing, he was considered one of the better pitchers in baseball. He rewarded the Yankees with a 4.91 ERA, 100 fewer strikeouts than the previous season, and an absolute implosion against the hated Red Sox. In game 7 of the horrific 2004 ALCS, he pitched two innings giving up five walks and three runs. The Yankees were able to trade away the final three years of the contract and get away. So why is he on the list?

Well, the Yankees did not learn. A few years later, after a stellar season in Atlanta where he struck out 238 with a 2.87 ERA, the Yankees brought him back to New York yet again. Well, this time he would raise his ERA to 5.32 and again strike out more than 100 batters less than the year before. He was a bad signing not once but twice and that is how he makes it into number five on my list of Yankees worst free agent signings.

Rich –  Jose Contreras is my choice for the fifth worst free agent signing in Yankees history.  Going after Jose Contreras is how the Yankees earned the title of “The Evil Empire” by Larry Luchino and the Boston Red Sox (the Yankees pulled some shady things to help limit other teams access to Jose like renting out entire hotel floors etc.).  The Yankees signed the Cuban superstar for four years and $32 million, not a bad amount in the winter of 2003.  Contreras was a decent pitcher over his 11 year MLB career, but his best years came as a member of the Chicago White Sox (he was traded to the White Sox after just under 2 years with the Yankees for Esteban Loaiza).  On the Yankees, he was routinely injured, and only made 27 starts (was relegated to the bullpen at one point) and only pitched in 166 innings, and he went 15-7 with an ERA of 4.64, and a WHIP of 1.302.  Like I said, he wasn’t a bad pitcher, but the injuries and lack of production didn’t live up to the hype.

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