Yankees worst free agent contracts ever handed out

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Such a strange year was 2013. The Yanks missed the playoffs, it was their worst finish since 1992, and they had Kevin Youkilis under contract. That’s right, a player embedded into Red Sox lore spent time in pinstripes (shocker).

Youkilis’ contract wasn’t horrible by any means; it was a relatively fair 1-year, $12 million deal. But he was just flat outdone as a major league player. He batted an abysmal .219 with two homers and eight RBIs in 105 at-bats.

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He even went to Japan the next season before retiring. That 2013 roster was so strange looking back on. So many recognizable names past their primes — Lyle Overbay, Alfonso Soriano, Ichiro, Vernon Wells, Travis Haffner, even Andy Pettitte put off his retirement for another year to share his last season with Mariano Rivera.

Then there’s the big one. Alex Rodriguez. It’s almost impossible to talk about Yankee contracts without talking about A-Rod. His 2007 re-signing was massive and back loaded — 10 years, $275 million. Jeez.

A-Rod had immense, God-given talent, but father time claims all, and A-Rod was no exemption. If anything, it came after him harder than anyone else. The speed Rodriguez once had all but evaporated in his later years.

He was a shell of still being paid superstar money. But those first few years of the contract were arguably well worth it, as his postseason homers in 2009 were crucial. Back then, Rodriguez appeared timeless.

Next. Yankees recent history shows they won’t overspend on an ace. dark

So, sound off in the comments. Who do you think had the worst contract in Yankee history? It’s undoubtedly a difficult choice with all the candidates available.