5 worst contracts in modern New York Yankees history

2. Carl Pavano

Hey, happy 46th birthday a few days ago, Carl Pavano! You were the absolute worst variety of Yankee signing.

Yes, even more insufferable than the No. 1 spot on our list.

After all, you’ve got to love a guy who takes big money, spends the entirety of his contract injured, then immediately gains a second wind after joining another team, vowing (and exacting!) revenge on a team that did nothing wrong.

Seriously, how can you go scorched earth on the Yankees for three years of … having to deal with you being a staggering disappointment? It’s the kind of thing that seems to happen to this team all the time. Former Yankees who struggled in pinstripes saving their very best for the team that “wronged” them by twiddling their thumbs and not receiving results.

Carl Pavano, a former Red Sox top prospect and Connecticut native, turned down larger offers from Boston, Detroit and Cincy to sign a four-year, $39.95 million contract with the Yankees after the 2004 season. The post-2004 “we lost badly!” pitching splurge doesn’t get nearly the hatred of the 2014 spending spree, but it was stunningly pointless in retrospect.

The move made sense! Pavano, just 29, was coming off a special season in Florida where he threw 222.1 innings, kept the ball on the ground, and finished sixth in the Cy Young voting (18-8, 3.00). He began 2005 with a 4–2 record and a 3.69 in 10 starts before succumbing to shoulder pain, throwing off the trajectory of his campaign.

Then came 2006, a disaster unlike any other. He missed the start of the year with a literal bruised ass, suffering a buttocks injury in the spring. He then proceeded not to pitch at all at the MLB level, making a few rehab starts before breaking his ribs in a mid-summer car accident and then not telling the Yankees about it until the day before he was supposed to be activated. Again, does this sound like someone who was “wronged”? In 2007, he returned, struggled, and had Tommy John surgery, returning to make seven starts with a 5.77 ERA in 2008.

In 2009, he left … and threw 199.1 innings immediately, split between Cleveland and Minnesota, where he met the Yankees in Game 3 of the ALDS! Luckily, this story has a happy ending. As red as Pavano’s ass still was, for whatever reason, he carried a shutout into the seventh inning of that game, at which point Alex Rodriguez hit a baseball so hard off him to right-center that it unraveled and turned to dust when it struck the baggie at the Metrodome. He also gave up a dinger to Jorge Posada minutes later, officially taking the L in the game and the series.

In 2010, he tried again. After a dominant season (17-11, 3.75 ERA, COME ON HOW IS THAT POSSIBLE?!), Pavano again lost Game 2 of the ALDS this time, giving up a tie-breaking homer to Lance Berkman.

Sorry, man. Maybe don’t try to cover up a car accident next time? Would love to hear Pavano’s side of the story. As of now, I’ll never get it.